JPWO2017122649A1 - フッ素原子含有化合物及びその利用 - Google Patents
フッ素原子含有化合物及びその利用 Download PDFInfo
- Publication number
- JPWO2017122649A1 JPWO2017122649A1 JP2017561119A JP2017561119A JPWO2017122649A1 JP WO2017122649 A1 JPWO2017122649 A1 JP WO2017122649A1 JP 2017561119 A JP2017561119 A JP 2017561119A JP 2017561119 A JP2017561119 A JP 2017561119A JP WO2017122649 A1 JPWO2017122649 A1 JP WO2017122649A1
- Authority
- JP
- Japan
- Prior art keywords
- group
- chloride
- carbon atoms
- fluoro
- atom
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 125000001153 fluoro group Chemical group F* 0.000 title claims abstract description 91
- 150000001875 compounds Chemical class 0.000 title claims abstract description 89
- 229910052731 fluorine Inorganic materials 0.000 title claims abstract description 80
- 125000003118 aryl group Chemical group 0.000 claims abstract description 30
- -1 2- (trifluoromethyl) phenyl group Chemical group 0.000 claims description 280
- 125000004432 carbon atom Chemical group C* 0.000 claims description 131
- 239000002966 varnish Substances 0.000 claims description 62
- 125000000217 alkyl group Chemical group 0.000 claims description 54
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 54
- 238000000034 method Methods 0.000 claims description 33
- 239000010409 thin film Substances 0.000 claims description 33
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 32
- 229910052799 carbon Inorganic materials 0.000 claims description 29
- 125000005843 halogen group Chemical group 0.000 claims description 28
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 20
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 20
- 229910052801 chlorine Inorganic materials 0.000 claims description 20
- 229910052740 iodine Inorganic materials 0.000 claims description 20
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 19
- 239000000463 material Substances 0.000 claims description 19
- 239000003960 organic solvent Substances 0.000 claims description 19
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 18
- 238000005401 electroluminescence Methods 0.000 claims description 18
- 239000002019 doping agent Substances 0.000 claims description 17
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 13
- 125000001188 haloalkyl group Chemical group 0.000 claims description 10
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 8
- 125000005348 fluorocycloalkyl group Chemical group 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000004407 fluoroaryl group Chemical group 0.000 claims description 6
- 125000003107 substituted aryl group Chemical group 0.000 claims description 6
- 125000004986 diarylamino group Chemical group 0.000 claims description 5
- 150000004820 halides Chemical class 0.000 claims description 5
- 125000002577 pseudohalo group Chemical group 0.000 claims description 4
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 3
- 239000010410 layer Substances 0.000 description 53
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 42
- 239000002904 solvent Substances 0.000 description 39
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 34
- 238000006243 chemical reaction Methods 0.000 description 32
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 26
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- 230000015572 biosynthetic process Effects 0.000 description 22
- 239000000706 filtrate Substances 0.000 description 22
- 238000003786 synthesis reaction Methods 0.000 description 22
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- 239000000203 mixture Substances 0.000 description 19
- 239000000758 substrate Substances 0.000 description 19
- 238000002347 injection Methods 0.000 description 18
- 239000007924 injection Substances 0.000 description 18
- 229910052757 nitrogen Inorganic materials 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- 238000005160 1H NMR spectroscopy Methods 0.000 description 17
- 239000000725 suspension Substances 0.000 description 17
- 238000001914 filtration Methods 0.000 description 15
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 15
- 125000003342 alkenyl group Chemical group 0.000 description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- 239000010408 film Substances 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- 230000005525 hole transport Effects 0.000 description 12
- 238000005259 measurement Methods 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- IRZFQKXEKAODTJ-UHFFFAOYSA-M sodium;propan-2-yloxymethanedithioate Chemical group [Na+].CC(C)OC([S-])=S IRZFQKXEKAODTJ-UHFFFAOYSA-M 0.000 description 11
- 125000000304 alkynyl group Chemical group 0.000 description 10
- 239000002994 raw material Substances 0.000 description 10
- 238000007789 sealing Methods 0.000 description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 10
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 150000001721 carbon Chemical group 0.000 description 9
- 238000000576 coating method Methods 0.000 description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 125000001072 heteroaryl group Chemical group 0.000 description 8
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 7
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 7
- 150000001448 anilines Chemical class 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- 235000011181 potassium carbonates Nutrition 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 125000000542 sulfonic acid group Chemical group 0.000 description 7
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- 239000012298 atmosphere Substances 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 6
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 6
- 239000004810 polytetrafluoroethylene Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000007740 vapor deposition Methods 0.000 description 6
- VRLCFIBHVFTRES-UHFFFAOYSA-N 1,1,2,3,3-pentafluoroprop-1-ene Chemical group F[C](F)C(F)=C(F)F VRLCFIBHVFTRES-UHFFFAOYSA-N 0.000 description 5
- XWCKIXLTBNGIHV-UHFFFAOYSA-N 2,3,4,5-tetrafluorobenzoyl chloride Chemical compound FC1=CC(C(Cl)=O)=C(F)C(F)=C1F XWCKIXLTBNGIHV-UHFFFAOYSA-N 0.000 description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
- 125000003172 aldehyde group Chemical group 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 239000007810 chemical reaction solvent Substances 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 125000003396 thiol group Chemical group [H]S* 0.000 description 5
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 5
- XMFMIKSWEJRJQE-UHFFFAOYSA-N 2,3,4,5-tetrafluorobenzamide Chemical compound NC(=O)C1=CC(F)=C(F)C(F)=C1F XMFMIKSWEJRJQE-UHFFFAOYSA-N 0.000 description 4
- QCAHUFWKIQLBNB-UHFFFAOYSA-N 3-(3-methoxypropoxy)propan-1-ol Chemical compound COCCCOCCCO QCAHUFWKIQLBNB-UHFFFAOYSA-N 0.000 description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- 229940126062 Compound A Drugs 0.000 description 4
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 4
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 238000004140 cleaning Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 125000004991 fluoroalkenyl group Chemical group 0.000 description 4
- 239000002346 layers by function Substances 0.000 description 4
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 4
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 239000012046 mixed solvent Substances 0.000 description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 4
- 239000011148 porous material Substances 0.000 description 4
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000006161 Suzuki-Miyaura coupling reaction Methods 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 3
- 229910000024 caesium carbonate Inorganic materials 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- QWXYZCJEXYQNEI-OSZHWHEXSA-N intermediate I Chemical compound COC(=O)[C@@]1(C=O)[C@H]2CC=[N+](C\C2=C\C)CCc2c1[nH]c1ccccc21 QWXYZCJEXYQNEI-OSZHWHEXSA-N 0.000 description 3
- GXMIHVHJTLPVKL-UHFFFAOYSA-N n,n,2-trimethylpropanamide Chemical compound CC(C)C(=O)N(C)C GXMIHVHJTLPVKL-UHFFFAOYSA-N 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 229940078552 o-xylene Drugs 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- DHRLEVQXOMLTIM-UHFFFAOYSA-N phosphoric acid;trioxomolybdenum Chemical compound O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.OP(O)(O)=O DHRLEVQXOMLTIM-UHFFFAOYSA-N 0.000 description 3
- IYDGMDWEHDFVQI-UHFFFAOYSA-N phosphoric acid;trioxotungsten Chemical compound O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O IYDGMDWEHDFVQI-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 235000011009 potassium phosphates Nutrition 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- 239000001211 (E)-4-phenylbut-3-en-2-one Substances 0.000 description 2
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 2
- ONUFSRWQCKNVSL-UHFFFAOYSA-N 1,2,3,4,5-pentafluoro-6-(2,3,4,5,6-pentafluorophenyl)benzene Chemical group FC1=C(F)C(F)=C(F)C(F)=C1C1=C(F)C(F)=C(F)C(F)=C1F ONUFSRWQCKNVSL-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- UDONPJKEOAWFGI-UHFFFAOYSA-N 1-methyl-3-phenoxybenzene Chemical compound CC1=CC=CC(OC=2C=CC=CC=2)=C1 UDONPJKEOAWFGI-UHFFFAOYSA-N 0.000 description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 2
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 2
- RMQCEYDJRVXDDD-UHFFFAOYSA-N 2-(trifluoromethyl)benzenecarbothioyl chloride Chemical compound FC(F)(F)C1=CC=CC=C1C(Cl)=S RMQCEYDJRVXDDD-UHFFFAOYSA-N 0.000 description 2
- PKURFTDCIWJBDF-UHFFFAOYSA-N 2-hexylnaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(CCCCCC)=CC=C21 PKURFTDCIWJBDF-UHFFFAOYSA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 2
- CUJHDWFNNBTXTG-UHFFFAOYSA-N 4-[9-(4-aminophenyl)-2,7-bis(4-carbazol-9-ylphenyl)fluoren-9-yl]aniline Chemical compound Nc1ccc(cc1)C1(c2cc(ccc2-c2ccc(cc12)-c1ccc(cc1)-n1c2ccccc2c2ccccc12)-c1ccc(cc1)-n1c2ccccc2c2ccccc12)c1ccc(N)cc1 CUJHDWFNNBTXTG-UHFFFAOYSA-N 0.000 description 2
- SWUBEMMFTUPINB-UHFFFAOYSA-N 9-[3-carbazol-9-yl-5-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]carbazole Chemical compound C1=CC=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=C(C=C(C=2)N2C3=CC=CC=C3C3=CC=CC=C32)N2C3=CC=CC=C3C3=CC=CC=C32)=N1 SWUBEMMFTUPINB-UHFFFAOYSA-N 0.000 description 2
- 108091006149 Electron carriers Proteins 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 101150003085 Pdcl gene Proteins 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 0 [Al]*N*1C=CC(C2(c3ccccc3-c3c2cccc3)c2ccccc2)=CC=C1 Chemical compound [Al]*N*1C=CC(C2(c3ccccc3-c3c2cccc3)c2ccccc2)=CC=C1 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 239000005456 alcohol based solvent Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 125000002078 anthracen-1-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([*])=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
- 125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
- 125000005228 aryl sulfonate group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 229930008407 benzylideneacetone Natural products 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- HHNHBFLGXIUXCM-GFCCVEGCSA-N cyclohexylbenzene Chemical compound [CH]1CCCC[C@@H]1C1=CC=CC=C1 HHNHBFLGXIUXCM-GFCCVEGCSA-N 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- AOGQPLXWSUTHQB-UHFFFAOYSA-N hexyl acetate Chemical compound CCCCCCOC(C)=O AOGQPLXWSUTHQB-UHFFFAOYSA-N 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- YSBUANSGDLZTKV-UHFFFAOYSA-N n-phenylcarbamoyl chloride Chemical compound ClC(=O)NC1=CC=CC=C1 YSBUANSGDLZTKV-UHFFFAOYSA-N 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-SVYQBANQSA-N oxolane-d8 Chemical compound [2H]C1([2H])OC([2H])([2H])C([2H])([2H])C1([2H])[2H] WYURNTSHIVDZCO-SVYQBANQSA-N 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000011736 potassium bicarbonate Substances 0.000 description 2
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
- 235000015497 potassium bicarbonate Nutrition 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- 229910000160 potassium phosphate Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 2
- BWHOZHOGCMHOBV-BQYQJAHWSA-N trans-benzylideneacetone Chemical compound CC(=O)\C=C\C1=CC=CC=C1 BWHOZHOGCMHOBV-BQYQJAHWSA-N 0.000 description 2
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- IDQUIFLAFFZYEX-UHFFFAOYSA-N (3-carbazol-9-ylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC(N2C3=CC=CC=C3C3=CC=CC=C32)=C1 IDQUIFLAFFZYEX-UHFFFAOYSA-N 0.000 description 1
- JGAVTCVHDMOQTJ-UHFFFAOYSA-N (4-carbazol-9-ylphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 JGAVTCVHDMOQTJ-UHFFFAOYSA-N 0.000 description 1
- JWJQEUDGBZMPAX-UHFFFAOYSA-N (9-phenylcarbazol-3-yl)boronic acid Chemical compound C12=CC=CC=C2C2=CC(B(O)O)=CC=C2N1C1=CC=CC=C1 JWJQEUDGBZMPAX-UHFFFAOYSA-N 0.000 description 1
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
- 125000006649 (C2-C20) alkynyl group Chemical group 0.000 description 1
- DCTMXCOHGKSXIZ-UHFFFAOYSA-N (R)-1,3-Octanediol Chemical compound CCCCCC(O)CCO DCTMXCOHGKSXIZ-UHFFFAOYSA-N 0.000 description 1
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- 125000006013 1,1-difluoroethoxy group Chemical group 0.000 description 1
- 125000006002 1,1-difluoroethyl group Chemical group 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- KIBPOQOFHGSRNY-UHFFFAOYSA-N 1,5-dichloro-2-(chloromethyl)-4-fluoro-5-nitrocyclohexa-1,3-diene Chemical compound ClC1=C(CCl)C=C(C(C1)([N+](=O)[O-])Cl)F KIBPOQOFHGSRNY-UHFFFAOYSA-N 0.000 description 1
- OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 1
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 description 1
- ZLNVRXFZTPRLIK-UHFFFAOYSA-N 1-(chloromethyl)-2,3,4,5,6-pentafluorobenzene Chemical compound FC1=C(F)C(F)=C(CCl)C(F)=C1F ZLNVRXFZTPRLIK-UHFFFAOYSA-N 0.000 description 1
- FPIUHZTVPROGQE-UHFFFAOYSA-N 1-(chloromethyl)-2,3,4,5-tetrafluoro-6-nitrobenzene Chemical compound FC1=C(CCl)C(=C(C(=C1F)F)F)[N+](=O)[O-] FPIUHZTVPROGQE-UHFFFAOYSA-N 0.000 description 1
- PVSKKLFYHHQKFR-UHFFFAOYSA-N 1-(chloromethyl)-2,3,4,5-tetrafluorobenzene Chemical compound FC1=CC(CCl)=C(F)C(F)=C1F PVSKKLFYHHQKFR-UHFFFAOYSA-N 0.000 description 1
- RLWBYURQFNYMIW-UHFFFAOYSA-N 1-(chloromethyl)-2,3,4-trifluorobenzene Chemical compound FC1=CC=C(CCl)C(F)=C1F RLWBYURQFNYMIW-UHFFFAOYSA-N 0.000 description 1
- WCOSFWYZZNLKLX-UHFFFAOYSA-N 1-(chloromethyl)-2,3,5,6-tetrafluoro-4-(1,2,2-trifluoroethenyl)benzene Chemical compound FC1=C(CCl)C(=C(C(=C1F)C(=C(F)F)F)F)F WCOSFWYZZNLKLX-UHFFFAOYSA-N 0.000 description 1
- LXQPOEOIIDQDDB-UHFFFAOYSA-N 1-(chloromethyl)-2,3,5,6-tetrafluoro-4-(trifluoromethyl)benzene Chemical compound FC1=C(F)C(C(F)(F)F)=C(F)C(F)=C1CCl LXQPOEOIIDQDDB-UHFFFAOYSA-N 0.000 description 1
- IEKYTIJMIUKVMR-UHFFFAOYSA-N 1-(chloromethyl)-2,3,5,6-tetrafluoro-4-methylbenzene Chemical compound CC1=C(F)C(F)=C(CCl)C(F)=C1F IEKYTIJMIUKVMR-UHFFFAOYSA-N 0.000 description 1
- GUCWYIVGQZRLNJ-UHFFFAOYSA-N 1-(chloromethyl)-2,3,5-trifluorobenzene Chemical compound FC1=C(CCl)C=C(C=C1F)F GUCWYIVGQZRLNJ-UHFFFAOYSA-N 0.000 description 1
- OVUKQQRPTLPXTD-UHFFFAOYSA-N 1-(chloromethyl)-2,3-difluorobenzene Chemical compound FC1=CC=CC(CCl)=C1F OVUKQQRPTLPXTD-UHFFFAOYSA-N 0.000 description 1
- JMXPOOVDUVHJRO-UHFFFAOYSA-N 1-(chloromethyl)-2,4,5-trifluorobenzene Chemical compound FC1=CC(F)=C(CCl)C=C1F JMXPOOVDUVHJRO-UHFFFAOYSA-N 0.000 description 1
- XPGHWBDZNQUUQD-UHFFFAOYSA-N 1-(chloromethyl)-2,4-difluorobenzene Chemical compound FC1=CC=C(CCl)C(F)=C1 XPGHWBDZNQUUQD-UHFFFAOYSA-N 0.000 description 1
- BBXDMCQDLOCXRA-UHFFFAOYSA-N 1-(chloromethyl)-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1CCl BBXDMCQDLOCXRA-UHFFFAOYSA-N 0.000 description 1
- NLCDSGYIRRQYEA-UHFFFAOYSA-N 1-(chloromethyl)-2-fluoro-3-(trifluoromethyl)benzene Chemical compound FC1=C(CCl)C=CC=C1C(F)(F)F NLCDSGYIRRQYEA-UHFFFAOYSA-N 0.000 description 1
- FFJVADDDXFORRX-UHFFFAOYSA-N 1-(chloromethyl)-2-fluoro-4-methylbenzene Chemical compound CC1=CC=C(CCl)C(F)=C1 FFJVADDDXFORRX-UHFFFAOYSA-N 0.000 description 1
- HIDSJCQJOQDPEO-UHFFFAOYSA-N 1-(chloromethyl)-2-fluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(CCl)C(F)=C1 HIDSJCQJOQDPEO-UHFFFAOYSA-N 0.000 description 1
- MOBRMRJUKNQBMY-UHFFFAOYSA-N 1-(chloromethyl)-2-fluorobenzene Chemical compound FC1=CC=CC=C1CCl MOBRMRJUKNQBMY-UHFFFAOYSA-N 0.000 description 1
- OINTXXMBRBLMHH-UHFFFAOYSA-N 1-(chloromethyl)-3,5-bis(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC(CCl)=CC(C(F)(F)F)=C1 OINTXXMBRBLMHH-UHFFFAOYSA-N 0.000 description 1
- VNGSMSFVLAAOGK-UHFFFAOYSA-N 1-(chloromethyl)-3,5-difluorobenzene Chemical compound FC1=CC(F)=CC(CCl)=C1 VNGSMSFVLAAOGK-UHFFFAOYSA-N 0.000 description 1
- XGASTRVQNVVYIZ-UHFFFAOYSA-N 1-(chloromethyl)-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(CCl)=C1 XGASTRVQNVVYIZ-UHFFFAOYSA-N 0.000 description 1
- UYPQFFOMZPINFM-UHFFFAOYSA-N 1-(chloromethyl)-3-fluoro-2-nitrobenzene Chemical compound [O-][N+](=O)c1c(F)cccc1CCl UYPQFFOMZPINFM-UHFFFAOYSA-N 0.000 description 1
- UNZBMTCZGLEHHO-UHFFFAOYSA-N 1-(chloromethyl)-3-fluoro-5-(trifluoromethyl)benzene Chemical compound FC1=CC(CCl)=CC(C(F)(F)F)=C1 UNZBMTCZGLEHHO-UHFFFAOYSA-N 0.000 description 1
- XBDXMDVEZLOGMC-UHFFFAOYSA-N 1-(chloromethyl)-3-fluorobenzene Chemical compound FC1=CC=CC(CCl)=C1 XBDXMDVEZLOGMC-UHFFFAOYSA-N 0.000 description 1
- XAAVHHVOSNAXJG-UHFFFAOYSA-N 1-(chloromethyl)-4-(1,1,2,2,2-pentafluoroethyl)benzene Chemical compound FC(C(F)(F)F)(C1=CC=C(CCl)C=C1)F XAAVHHVOSNAXJG-UHFFFAOYSA-N 0.000 description 1
- MCHDHQVROPEJJT-UHFFFAOYSA-N 1-(chloromethyl)-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(CCl)C=C1 MCHDHQVROPEJJT-UHFFFAOYSA-N 0.000 description 1
- FZTZSNPJDFLZOZ-UHFFFAOYSA-N 1-(chloromethyl)-4-fluoro-2-(trifluoromethyl)benzene Chemical compound FC1=CC=C(CCl)C(C(F)(F)F)=C1 FZTZSNPJDFLZOZ-UHFFFAOYSA-N 0.000 description 1
- BQQAXQSWBZWPAQ-UHFFFAOYSA-N 1-(chloromethyl)-4-fluoro-2-methylbenzene Chemical compound CC1=CC(F)=CC=C1CCl BQQAXQSWBZWPAQ-UHFFFAOYSA-N 0.000 description 1
- DUWNMKQNZAEBMZ-UHFFFAOYSA-N 1-(chloromethyl)-4-fluoro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(F)=CC=C1CCl DUWNMKQNZAEBMZ-UHFFFAOYSA-N 0.000 description 1
- IZXWCDITFDNEBY-UHFFFAOYSA-N 1-(chloromethyl)-4-fluorobenzene Chemical compound FC1=CC=C(CCl)C=C1 IZXWCDITFDNEBY-UHFFFAOYSA-N 0.000 description 1
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
- JNEFYNWPEMTPEB-UHFFFAOYSA-N 1-bromo-2-(chloromethyl)-3-fluorobenzene Chemical compound FC1=CC=CC(Br)=C1CCl JNEFYNWPEMTPEB-UHFFFAOYSA-N 0.000 description 1
- OPMKPLUMLVBPET-UHFFFAOYSA-N 1-bromo-2-(chloromethyl)-4-fluorobenzene Chemical compound FC1=CC=C(Br)C(CCl)=C1 OPMKPLUMLVBPET-UHFFFAOYSA-N 0.000 description 1
- KQLBOTQKXUSZMJ-UHFFFAOYSA-N 1-bromo-3-(chloromethyl)-2-fluorobenzene Chemical compound FC1=C(Br)C=CC=C1CCl KQLBOTQKXUSZMJ-UHFFFAOYSA-N 0.000 description 1
- MJGOLNNLNQQIHR-UHFFFAOYSA-N 1-chloro-2-(chloromethyl)-3-fluorobenzene Chemical compound FC1=CC=CC(Cl)=C1CCl MJGOLNNLNQQIHR-UHFFFAOYSA-N 0.000 description 1
- WHIYGQHPMKXCBH-UHFFFAOYSA-N 1-chloro-2-(chloromethyl)-4-fluorobenzene Chemical compound FC1=CC=C(Cl)C(CCl)=C1 WHIYGQHPMKXCBH-UHFFFAOYSA-N 0.000 description 1
- YLTYCUOGVPKILN-UHFFFAOYSA-N 1-chloro-3-(chloromethyl)-2-fluorobenzene Chemical compound FC1=C(Cl)C=CC=C1CCl YLTYCUOGVPKILN-UHFFFAOYSA-N 0.000 description 1
- XKFGZKBYLFDLMS-UHFFFAOYSA-N 1-chloro-3-(chloromethyl)-5-fluorobenzene Chemical compound FC1=CC(Cl)=CC(CCl)=C1 XKFGZKBYLFDLMS-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- 125000006420 1-fluorocyclopropyl group Chemical group [H]C1([H])C([H])([H])C1(F)* 0.000 description 1
- 125000004790 1-fluoroethoxy group Chemical group FC(C)O* 0.000 description 1
- 125000004776 1-fluoroethyl group Chemical group [H]C([H])([H])C([H])(F)* 0.000 description 1
- 125000006019 1-methyl-1-propenyl group Chemical group 0.000 description 1
- 125000006021 1-methyl-2-propenyl group Chemical group 0.000 description 1
- 125000006018 1-methyl-ethenyl group Chemical group 0.000 description 1
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 description 1
- YQTCYDZONRUIEZ-UHFFFAOYSA-N 2,3,4,5,6-pentafluorobenzenecarbothioyl chloride Chemical compound FC1=C(F)C(F)=C(C(Cl)=S)C(F)=C1F YQTCYDZONRUIEZ-UHFFFAOYSA-N 0.000 description 1
- UOJCTEGNHXRPKO-UHFFFAOYSA-N 2,3,4,5,6-pentafluorobenzenesulfonyl chloride Chemical compound FC1=C(F)C(F)=C(S(Cl)(=O)=O)C(F)=C1F UOJCTEGNHXRPKO-UHFFFAOYSA-N 0.000 description 1
- KNSAASMUGPIKMC-UHFFFAOYSA-N 2,3,4,5-tetrafluoro-6-nitrobenzenecarbothioyl chloride Chemical compound FC1=C(C(=S)Cl)C(=C(C(=C1F)F)F)[N+](=O)[O-] KNSAASMUGPIKMC-UHFFFAOYSA-N 0.000 description 1
- SPOZTRXNFPGAQC-UHFFFAOYSA-N 2,3,4,5-tetrafluoro-6-nitrobenzenesulfonyl chloride Chemical compound FC1=C(C(=C(C(=C1F)F)F)[N+](=O)[O-])S(=O)(=O)Cl SPOZTRXNFPGAQC-UHFFFAOYSA-N 0.000 description 1
- RUGZVPRCKQMYAZ-UHFFFAOYSA-N 2,3,4,5-tetrafluoro-6-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=C(F)C(F)=C(F)C(F)=C1C(Cl)=O RUGZVPRCKQMYAZ-UHFFFAOYSA-N 0.000 description 1
- LXOPOQFUWROOMK-UHFFFAOYSA-N 2,3,4-trifluorobenzenecarbothioyl chloride Chemical compound FC1=C(C(=S)Cl)C=CC(=C1F)F LXOPOQFUWROOMK-UHFFFAOYSA-N 0.000 description 1
- XFTDZYFHXRZLEF-UHFFFAOYSA-N 2,3,4-trifluorobenzenesulfonyl chloride Chemical compound FC1=CC=C(S(Cl)(=O)=O)C(F)=C1F XFTDZYFHXRZLEF-UHFFFAOYSA-N 0.000 description 1
- NXRQXCFBZGIRGN-UHFFFAOYSA-N 2,3,4-trifluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C(F)=C1F NXRQXCFBZGIRGN-UHFFFAOYSA-N 0.000 description 1
- QFXPAFKAJVBROC-UHFFFAOYSA-N 2,3,5,6-tetrafluoro-4-(1,2,2-trifluoroethenyl)benzenecarbothioyl chloride Chemical compound FC1=C(C(=S)Cl)C(=C(C(=C1F)C(=C(F)F)F)F)F QFXPAFKAJVBROC-UHFFFAOYSA-N 0.000 description 1
- XREXMQVYVUMIJB-UHFFFAOYSA-N 2,3,5,6-tetrafluoro-4-(1,2,2-trifluoroethenyl)benzenesulfonyl chloride Chemical compound FC1=C(C(=C(C(=C1F)C(=C(F)F)F)F)F)S(=O)(=O)Cl XREXMQVYVUMIJB-UHFFFAOYSA-N 0.000 description 1
- NQSNPVFVRVPSTN-UHFFFAOYSA-N 2,3,5,6-tetrafluoro-4-(trifluoromethyl)benzenecarbothioyl chloride Chemical compound FC1=C(C(=S)Cl)C(=C(C(=C1F)C(F)(F)F)F)F NQSNPVFVRVPSTN-UHFFFAOYSA-N 0.000 description 1
- FHFMCKBNFUVUDT-UHFFFAOYSA-N 2,3,5,6-tetrafluoro-4-(trifluoromethyl)benzoyl chloride Chemical compound FC1=C(F)C(C(F)(F)F)=C(F)C(F)=C1C(Cl)=O FHFMCKBNFUVUDT-UHFFFAOYSA-N 0.000 description 1
- HOWIJXXJTRRUMM-UHFFFAOYSA-N 2,3,5,6-tetrafluoro-4-methylbenzenecarbothioyl chloride Chemical compound FC1=C(C(=S)Cl)C(=C(C(=C1F)C)F)F HOWIJXXJTRRUMM-UHFFFAOYSA-N 0.000 description 1
- BCLOLHGRBBHSEB-UHFFFAOYSA-N 2,3,5,6-tetrafluoro-4-methylbenzenesulfonyl chloride Chemical compound C1(=C(C(=C(C(=C1F)S(=O)(=O)Cl)F)F)C)F BCLOLHGRBBHSEB-UHFFFAOYSA-N 0.000 description 1
- SCFPILCRJUUNLP-UHFFFAOYSA-N 2,3,5,6-tetrafluoro-4-methylbenzoyl chloride Chemical compound CC1=C(F)C(F)=C(C(Cl)=O)C(F)=C1F SCFPILCRJUUNLP-UHFFFAOYSA-N 0.000 description 1
- QNEANEWDLHYOMZ-UHFFFAOYSA-N 2,3,5,6-tetrafluorobenzenecarbothioyl chloride Chemical compound FC1=C(C(=S)Cl)C(=C(C=C1F)F)F QNEANEWDLHYOMZ-UHFFFAOYSA-N 0.000 description 1
- WQJDRBBQQXGDNZ-UHFFFAOYSA-N 2,3,5,6-tetrafluorobenzenesulfonyl chloride Chemical compound FC1=CC(F)=C(F)C(S(Cl)(=O)=O)=C1F WQJDRBBQQXGDNZ-UHFFFAOYSA-N 0.000 description 1
- AELMDUZWKHVPIF-UHFFFAOYSA-N 2,3,5,6-tetrafluorobenzoyl chloride Chemical compound FC1=CC(F)=C(F)C(C(Cl)=O)=C1F AELMDUZWKHVPIF-UHFFFAOYSA-N 0.000 description 1
- QTIPHWWHHRFTNO-UHFFFAOYSA-N 2,3,5-trifluorobenzoyl chloride Chemical compound FC1=CC(F)=C(F)C(C(Cl)=O)=C1 QTIPHWWHHRFTNO-UHFFFAOYSA-N 0.000 description 1
- SZTFWSJRXBEVSX-UHFFFAOYSA-N 2,3,6-trifluorobenzenecarbothioyl chloride Chemical compound FC1=C(C(=S)Cl)C(=CC=C1F)F SZTFWSJRXBEVSX-UHFFFAOYSA-N 0.000 description 1
- DMUGJQMADYEWSQ-UHFFFAOYSA-N 2,3,6-trifluorobenzoyl chloride Chemical compound FC1=CC=C(F)C(C(Cl)=O)=C1F DMUGJQMADYEWSQ-UHFFFAOYSA-N 0.000 description 1
- FWSKALITQIVFBA-UHFFFAOYSA-N 2,3-difluorobenzenecarbothioyl chloride Chemical compound FC1=C(C(=S)Cl)C=CC=C1F FWSKALITQIVFBA-UHFFFAOYSA-N 0.000 description 1
- VHCVYGNNCGAWBP-UHFFFAOYSA-N 2,3-difluorobenzenesulfonyl chloride Chemical compound FC1=CC=CC(S(Cl)(=O)=O)=C1F VHCVYGNNCGAWBP-UHFFFAOYSA-N 0.000 description 1
- CDCFERWURRNLLA-UHFFFAOYSA-N 2,3-difluorobenzoyl chloride Chemical compound FC1=CC=CC(C(Cl)=O)=C1F CDCFERWURRNLLA-UHFFFAOYSA-N 0.000 description 1
- QBDAFARLDLCWAT-UHFFFAOYSA-N 2,3-dihydropyran-6-one Chemical compound O=C1OCCC=C1 QBDAFARLDLCWAT-UHFFFAOYSA-N 0.000 description 1
- ZZMVDONRUQBRTJ-UHFFFAOYSA-N 2,4,5-trifluoro-3-methyl-6-nitrobenzenesulfonyl chloride Chemical compound FC1=C(C(=C(C(=C1C)F)F)[N+](=O)[O-])S(=O)(=O)Cl ZZMVDONRUQBRTJ-UHFFFAOYSA-N 0.000 description 1
- IGBLDVIZBYMRCW-UHFFFAOYSA-N 2,4,5-trifluoro-3-methyl-6-nitrobenzoyl chloride Chemical compound CC1=C(F)C(F)=C([N+]([O-])=O)C(C(Cl)=O)=C1F IGBLDVIZBYMRCW-UHFFFAOYSA-N 0.000 description 1
- CUANBNYRWULDGI-UHFFFAOYSA-N 2,4,5-trifluorobenzenecarbothioyl chloride Chemical compound FC1=C(C(=S)Cl)C=C(C(=C1)F)F CUANBNYRWULDGI-UHFFFAOYSA-N 0.000 description 1
- STCZWXXRRTWRSK-UHFFFAOYSA-N 2,4,5-trifluorobenzenesulfonyl chloride Chemical compound FC1=CC(F)=C(S(Cl)(=O)=O)C=C1F STCZWXXRRTWRSK-UHFFFAOYSA-N 0.000 description 1
- STBGCAUUOPNJBH-UHFFFAOYSA-N 2,4,5-trifluorobenzoyl chloride Chemical compound FC1=CC(F)=C(C(Cl)=O)C=C1F STBGCAUUOPNJBH-UHFFFAOYSA-N 0.000 description 1
- UBACQSYWDWBYMJ-UHFFFAOYSA-N 2,4,6-trifluorobenzenecarbothioyl chloride Chemical compound FC1=C(C(=S)Cl)C(=CC(=C1)F)F UBACQSYWDWBYMJ-UHFFFAOYSA-N 0.000 description 1
- XINCBNCLCIQIJM-UHFFFAOYSA-N 2,4,6-trifluorobenzenesulfonyl chloride Chemical compound FC1=CC(F)=C(S(Cl)(=O)=O)C(F)=C1 XINCBNCLCIQIJM-UHFFFAOYSA-N 0.000 description 1
- SIFIJQFBERMWMU-UHFFFAOYSA-N 2,4,6-trifluorobenzoyl chloride Chemical compound FC1=CC(F)=C(C(Cl)=O)C(F)=C1 SIFIJQFBERMWMU-UHFFFAOYSA-N 0.000 description 1
- QSVXAAIZVOEAHE-UHFFFAOYSA-N 2,4,6-tris(trifluoromethyl)benzenecarbothioyl chloride Chemical compound FC(C1=C(C(=S)Cl)C(=CC(=C1)C(F)(F)F)C(F)(F)F)(F)F QSVXAAIZVOEAHE-UHFFFAOYSA-N 0.000 description 1
- NPZZWUGVSJMTRC-UHFFFAOYSA-N 2,4,6-tris(trifluoromethyl)benzenesulfonyl chloride Chemical compound FC(C1=C(C(=CC(=C1)C(F)(F)F)C(F)(F)F)S(=O)(=O)Cl)(F)F NPZZWUGVSJMTRC-UHFFFAOYSA-N 0.000 description 1
- YETUQCIZTJPWRS-UHFFFAOYSA-N 2,4-dichloro-5-fluoro-4-nitrocyclohexa-1,5-diene-1-carbonyl chloride Chemical compound ClC1=C(C(=O)Cl)C=C(C(C1)([N+](=O)[O-])Cl)F YETUQCIZTJPWRS-UHFFFAOYSA-N 0.000 description 1
- HLVQKMHAPXILIT-UHFFFAOYSA-N 2,4-dichloro-5-fluoro-4-nitrocyclohexa-1,5-diene-1-carbothioyl chloride Chemical compound ClC1=C(C(=S)Cl)C=C(C(C1)([N+](=O)[O-])Cl)F HLVQKMHAPXILIT-UHFFFAOYSA-N 0.000 description 1
- XKMLDGMMADVTSN-UHFFFAOYSA-N 2,4-dichloro-5-fluoro-4-nitrocyclohexa-1,5-diene-1-sulfonyl chloride Chemical compound ClC1=C(C=C(C(C1)([N+](=O)[O-])Cl)F)S(=O)(=O)Cl XKMLDGMMADVTSN-UHFFFAOYSA-N 0.000 description 1
- MTCVHLZVNBFVIG-UHFFFAOYSA-N 2,4-difluorobenzenecarbothioyl chloride Chemical compound FC1=C(C(=S)Cl)C=CC(=C1)F MTCVHLZVNBFVIG-UHFFFAOYSA-N 0.000 description 1
- FJSAJUXIHJIAMD-UHFFFAOYSA-N 2,4-difluorobenzenesulfonyl chloride Chemical compound FC1=CC=C(S(Cl)(=O)=O)C(F)=C1 FJSAJUXIHJIAMD-UHFFFAOYSA-N 0.000 description 1
- JSWRVDNTKPAJLB-UHFFFAOYSA-N 2,4-difluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C(F)=C1 JSWRVDNTKPAJLB-UHFFFAOYSA-N 0.000 description 1
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 1
- CKCPGERPKBKMDF-UHFFFAOYSA-N 2,5-difluorobenzenecarbothioyl chloride Chemical compound FC1=C(C(=S)Cl)C=C(C=C1)F CKCPGERPKBKMDF-UHFFFAOYSA-N 0.000 description 1
- CELLJWUVMKEJDY-UHFFFAOYSA-N 2,5-difluorobenzenesulfonyl chloride Chemical compound FC1=CC=C(F)C(S(Cl)(=O)=O)=C1 CELLJWUVMKEJDY-UHFFFAOYSA-N 0.000 description 1
- RLRUKKDFNWXXRT-UHFFFAOYSA-N 2,5-difluorobenzoyl chloride Chemical compound FC1=CC=C(F)C(C(Cl)=O)=C1 RLRUKKDFNWXXRT-UHFFFAOYSA-N 0.000 description 1
- TZLSRMNRCDHVTF-UHFFFAOYSA-N 2,6-difluorobenzenecarbothioyl chloride Chemical compound FC1=C(C(=S)Cl)C(=CC=C1)F TZLSRMNRCDHVTF-UHFFFAOYSA-N 0.000 description 1
- QXWAUQMMMIMLTO-UHFFFAOYSA-N 2,6-difluorobenzenesulfonyl chloride Chemical compound FC1=CC=CC(F)=C1S(Cl)(=O)=O QXWAUQMMMIMLTO-UHFFFAOYSA-N 0.000 description 1
- QRHUZEVERIHEPT-UHFFFAOYSA-N 2,6-difluorobenzoyl chloride Chemical compound FC1=CC=CC(F)=C1C(Cl)=O QRHUZEVERIHEPT-UHFFFAOYSA-N 0.000 description 1
- OIMWTJRLFZKCJJ-UHFFFAOYSA-N 2,7-dibromo-9,9-bis(4-nitrophenyl)fluorene Chemical compound [O-][N+](=O)C1=CC=C(C=C1)C1(C2=CC(Br)=CC=C2C2=C1C=C(Br)C=C2)C1=CC=C(C=C1)[N+]([O-])=O OIMWTJRLFZKCJJ-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
- VXQBJTKSVGFQOL-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethyl acetate Chemical compound CCCCOCCOCCOC(C)=O VXQBJTKSVGFQOL-UHFFFAOYSA-N 0.000 description 1
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical compound CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 1
- FRFNHABGFLDQOU-UHFFFAOYSA-N 2-(chloromethyl)-1,3,5-trifluorobenzene Chemical compound FC1=CC(F)=C(CCl)C(F)=C1 FRFNHABGFLDQOU-UHFFFAOYSA-N 0.000 description 1
- SJNPUJMOIINRPS-UHFFFAOYSA-N 2-(chloromethyl)-1,3,5-tris(trifluoromethyl)benzene Chemical compound FC(C1=C(CCl)C(=CC(=C1)C(F)(F)F)C(F)(F)F)(F)F SJNPUJMOIINRPS-UHFFFAOYSA-N 0.000 description 1
- MJXRENZUAQXZGJ-UHFFFAOYSA-N 2-(chloromethyl)-1,3-difluorobenzene Chemical compound FC1=CC=CC(F)=C1CCl MJXRENZUAQXZGJ-UHFFFAOYSA-N 0.000 description 1
- INXKTZMJFPRVAY-UHFFFAOYSA-N 2-(chloromethyl)-1,4-difluorobenzene Chemical compound FC1=CC=C(F)C(CCl)=C1 INXKTZMJFPRVAY-UHFFFAOYSA-N 0.000 description 1
- NVMNTWHOSXLNKZ-UHFFFAOYSA-N 2-(chloromethyl)-1-fluoro-3-(trifluoromethyl)benzene Chemical compound FC1=CC=CC(C(F)(F)F)=C1CCl NVMNTWHOSXLNKZ-UHFFFAOYSA-N 0.000 description 1
- AQEQIDYJUOAAQH-UHFFFAOYSA-N 2-(chloromethyl)-1-fluoro-3-iodobenzene Chemical compound FC1=C(C(=CC=C1)I)CCl AQEQIDYJUOAAQH-UHFFFAOYSA-N 0.000 description 1
- OZGWDDBROIXNRQ-UHFFFAOYSA-N 2-(chloromethyl)-1-fluoro-4-(trifluoromethyl)benzene Chemical compound FC1=CC=C(C(F)(F)F)C=C1CCl OZGWDDBROIXNRQ-UHFFFAOYSA-N 0.000 description 1
- XVPJABNPZBSPIK-UHFFFAOYSA-N 2-(chloromethyl)-1-fluoro-4-iodobenzene Chemical compound FC1=CC=C(I)C=C1CCl XVPJABNPZBSPIK-UHFFFAOYSA-N 0.000 description 1
- NRDFOZDHNQKLOO-UHFFFAOYSA-N 2-(chloromethyl)-1-fluoro-4-methylbenzene Chemical compound CC1=CC=C(F)C(CCl)=C1 NRDFOZDHNQKLOO-UHFFFAOYSA-N 0.000 description 1
- JXEGJILGVKWEMR-UHFFFAOYSA-N 2-(chloromethyl)-1-fluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C(CCl)=C1 JXEGJILGVKWEMR-UHFFFAOYSA-N 0.000 description 1
- IGURRQIIIXYJND-UHFFFAOYSA-N 2-(chloromethyl)-4-fluoro-1-(trifluoromethyl)benzene Chemical compound FC1=CC=C(C(F)(F)F)C(CCl)=C1 IGURRQIIIXYJND-UHFFFAOYSA-N 0.000 description 1
- MTKSHHODKOMICW-UHFFFAOYSA-N 2-(chloromethyl)-4-fluoro-1-methylbenzene Chemical compound CC1=CC=C(F)C=C1CCl MTKSHHODKOMICW-UHFFFAOYSA-N 0.000 description 1
- RRDMOQVRYCINEH-UHFFFAOYSA-N 2-(chloromethyl)-4-fluoro-1-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1CCl RRDMOQVRYCINEH-UHFFFAOYSA-N 0.000 description 1
- ZIZGWNOAHUCACM-UHFFFAOYSA-N 2-(trifluoromethyl)benzenesulfonyl chloride Chemical compound FC(F)(F)C1=CC=CC=C1S(Cl)(=O)=O ZIZGWNOAHUCACM-UHFFFAOYSA-N 0.000 description 1
- MXIUWSYTQJLIKE-UHFFFAOYSA-N 2-(trifluoromethyl)benzoyl chloride Chemical compound FC(F)(F)C1=CC=CC=C1C(Cl)=O MXIUWSYTQJLIKE-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 1
- IHCCLXNEEPMSIO-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 IHCCLXNEEPMSIO-UHFFFAOYSA-N 0.000 description 1
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 1
- KYNNNKFAVRPOBK-UHFFFAOYSA-N 2-bromo-1-(chloromethyl)-3-fluorobenzene Chemical compound FC1=CC=CC(CCl)=C1Br KYNNNKFAVRPOBK-UHFFFAOYSA-N 0.000 description 1
- WXESCQMTNVSFHX-UHFFFAOYSA-N 2-bromo-1-(chloromethyl)-4-fluorobenzene Chemical compound FC1=CC=C(CCl)C(Br)=C1 WXESCQMTNVSFHX-UHFFFAOYSA-N 0.000 description 1
- YZXLEQLNBFIGRR-UHFFFAOYSA-N 2-bromo-3-fluorobenzenesulfonyl chloride Chemical compound FC1=CC=CC(S(Cl)(=O)=O)=C1Br YZXLEQLNBFIGRR-UHFFFAOYSA-N 0.000 description 1
- BIDXHLMXMWMYJC-UHFFFAOYSA-N 2-bromo-3-fluorobenzoyl chloride Chemical compound FC1=CC=CC(C(Cl)=O)=C1Br BIDXHLMXMWMYJC-UHFFFAOYSA-N 0.000 description 1
- DHWBKAMNEHOWTR-UHFFFAOYSA-N 2-bromo-4-fluorobenzenecarbothioyl chloride Chemical compound BrC1=C(C(=S)Cl)C=CC(=C1)F DHWBKAMNEHOWTR-UHFFFAOYSA-N 0.000 description 1
- GJPWPFVLPNTOOL-UHFFFAOYSA-N 2-bromo-4-fluorobenzenesulfonyl chloride Chemical compound FC1=CC=C(S(Cl)(=O)=O)C(Br)=C1 GJPWPFVLPNTOOL-UHFFFAOYSA-N 0.000 description 1
- AXZRUTPBQMAWLP-UHFFFAOYSA-N 2-bromo-4-fluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C(Br)=C1 AXZRUTPBQMAWLP-UHFFFAOYSA-N 0.000 description 1
- FUDHLCUAEHWWFD-UHFFFAOYSA-N 2-bromo-5-fluorobenzenecarbothioyl chloride Chemical compound BrC1=C(C(=S)Cl)C=C(C=C1)F FUDHLCUAEHWWFD-UHFFFAOYSA-N 0.000 description 1
- JUJFSUADOZWKSR-UHFFFAOYSA-N 2-bromo-5-fluorobenzenesulfonyl chloride Chemical compound FC1=CC=C(Br)C(S(Cl)(=O)=O)=C1 JUJFSUADOZWKSR-UHFFFAOYSA-N 0.000 description 1
- XTODIZFNGWAEAZ-UHFFFAOYSA-N 2-bromo-6-fluorobenzenesulfonyl chloride Chemical compound FC1=CC=CC(Br)=C1S(Cl)(=O)=O XTODIZFNGWAEAZ-UHFFFAOYSA-N 0.000 description 1
- ZQOQNOOLDFFUDH-UHFFFAOYSA-N 2-bromo-6-fluorobenzoyl chloride Chemical compound FC1=CC=CC(Br)=C1C(Cl)=O ZQOQNOOLDFFUDH-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- PVTAFZLDYHBRRC-UHFFFAOYSA-N 2-chloro-1-(chloromethyl)-3-fluorobenzene Chemical compound FC1=CC=CC(CCl)=C1Cl PVTAFZLDYHBRRC-UHFFFAOYSA-N 0.000 description 1
- HMIAXVWVTBIGON-UHFFFAOYSA-N 2-chloro-1-(chloromethyl)-4-fluorobenzene Chemical compound FC1=CC=C(CCl)C(Cl)=C1 HMIAXVWVTBIGON-UHFFFAOYSA-N 0.000 description 1
- GFBKKJAGMDXUCL-UHFFFAOYSA-N 2-chloro-3-fluorobenzenecarbothioyl chloride Chemical compound ClC1=C(C(=S)Cl)C=CC=C1F GFBKKJAGMDXUCL-UHFFFAOYSA-N 0.000 description 1
- JGUJGYPYRWDTMV-UHFFFAOYSA-N 2-chloro-3-fluorobenzenesulfonyl chloride Chemical compound FC1=CC=CC(S(Cl)(=O)=O)=C1Cl JGUJGYPYRWDTMV-UHFFFAOYSA-N 0.000 description 1
- DIUKLCJZYOPHGW-UHFFFAOYSA-N 2-chloro-3-fluorobenzoyl chloride Chemical compound FC1=CC=CC(C(Cl)=O)=C1Cl DIUKLCJZYOPHGW-UHFFFAOYSA-N 0.000 description 1
- FIJYIJBXEJWINA-UHFFFAOYSA-N 2-chloro-4-fluorobenzenecarbothioyl chloride Chemical compound ClC1=C(C(=S)Cl)C=CC(=C1)F FIJYIJBXEJWINA-UHFFFAOYSA-N 0.000 description 1
- FCFPJKHVCHKCMP-UHFFFAOYSA-N 2-chloro-4-fluorobenzenesulfonyl chloride Chemical compound FC1=CC=C(S(Cl)(=O)=O)C(Cl)=C1 FCFPJKHVCHKCMP-UHFFFAOYSA-N 0.000 description 1
- POIAZJJVWRVLBO-UHFFFAOYSA-N 2-chloro-4-fluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C(Cl)=C1 POIAZJJVWRVLBO-UHFFFAOYSA-N 0.000 description 1
- MUAOMJKKQNIPAO-UHFFFAOYSA-N 2-chloro-5-fluorobenzenecarbothioyl chloride Chemical compound ClC1=C(C(=S)Cl)C=C(C=C1)F MUAOMJKKQNIPAO-UHFFFAOYSA-N 0.000 description 1
- IKUKZLDGZFXXNE-UHFFFAOYSA-N 2-chloro-5-fluorobenzenesulfonyl chloride Chemical compound FC1=CC=C(Cl)C(S(Cl)(=O)=O)=C1 IKUKZLDGZFXXNE-UHFFFAOYSA-N 0.000 description 1
- SGZSJPBASHYOHQ-UHFFFAOYSA-N 2-chloro-5-fluorobenzoyl chloride Chemical compound FC1=CC=C(Cl)C(C(Cl)=O)=C1 SGZSJPBASHYOHQ-UHFFFAOYSA-N 0.000 description 1
- ICTXXKXLYRVOQI-UHFFFAOYSA-N 2-chloro-6-fluorobenzenecarbothioyl chloride Chemical compound ClC1=C(C(=S)Cl)C(=CC=C1)F ICTXXKXLYRVOQI-UHFFFAOYSA-N 0.000 description 1
- FJSIDPINTJZFNS-UHFFFAOYSA-N 2-chloro-6-fluorobenzenesulfonyl chloride Chemical compound FC1=CC=CC(Cl)=C1S(Cl)(=O)=O FJSIDPINTJZFNS-UHFFFAOYSA-N 0.000 description 1
- GFNAJZAKJGKJCS-UHFFFAOYSA-N 2-chloro-6-fluorobenzoyl chloride Chemical compound FC1=CC=CC(Cl)=C1C(Cl)=O GFNAJZAKJGKJCS-UHFFFAOYSA-N 0.000 description 1
- WHKKNVAGWPTSRS-UHFFFAOYSA-N 2-dodecylnaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(CCCCCCCCCCCC)=CC=C21 WHKKNVAGWPTSRS-UHFFFAOYSA-N 0.000 description 1
- RXHTZICCFFSAGH-UHFFFAOYSA-N 2-fluoro-3-(trifluoromethyl)benzenecarbothioyl chloride Chemical compound FC1=C(C(=S)Cl)C=CC=C1C(F)(F)F RXHTZICCFFSAGH-UHFFFAOYSA-N 0.000 description 1
- RIKGRFSGIOOYEK-UHFFFAOYSA-N 2-fluoro-3-(trifluoromethyl)benzoyl chloride Chemical compound FC1=C(C(Cl)=O)C=CC=C1C(F)(F)F RIKGRFSGIOOYEK-UHFFFAOYSA-N 0.000 description 1
- APSBPZKWGAZIPU-UHFFFAOYSA-N 2-fluoro-4-methylbenzenecarbothioyl chloride Chemical compound FC1=C(C(=S)Cl)C=CC(=C1)C APSBPZKWGAZIPU-UHFFFAOYSA-N 0.000 description 1
- SDBFDPOFXLVGQF-UHFFFAOYSA-N 2-fluoro-4-methylbenzenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C(F)=C1 SDBFDPOFXLVGQF-UHFFFAOYSA-N 0.000 description 1
- SVSVOPWCUHQFAM-UHFFFAOYSA-N 2-fluoro-4-methylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C(F)=C1 SVSVOPWCUHQFAM-UHFFFAOYSA-N 0.000 description 1
- OOLBZYANQGKUAQ-UHFFFAOYSA-N 2-fluoro-4-nitrobenzenecarbothioyl chloride Chemical compound FC1=C(C(=S)Cl)C=CC(=C1)[N+](=O)[O-] OOLBZYANQGKUAQ-UHFFFAOYSA-N 0.000 description 1
- FNCNMVPZFVXQTL-UHFFFAOYSA-N 2-fluoro-4-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=C(S(Cl)(=O)=O)C(F)=C1 FNCNMVPZFVXQTL-UHFFFAOYSA-N 0.000 description 1
- BUBMAUUSVWQBMS-UHFFFAOYSA-N 2-fluoro-4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C(F)=C1 BUBMAUUSVWQBMS-UHFFFAOYSA-N 0.000 description 1
- UHYWZVNYBCOTTE-UHFFFAOYSA-N 2-fluoro-5-(trifluoromethyl)benzenecarbothioyl chloride Chemical compound FC1=C(C(=S)Cl)C=C(C=C1)C(F)(F)F UHYWZVNYBCOTTE-UHFFFAOYSA-N 0.000 description 1
- XTHDSFNKYHMRFZ-UHFFFAOYSA-N 2-fluoro-5-(trifluoromethyl)benzenesulfonyl chloride Chemical compound FC1=CC=C(C(F)(F)F)C=C1S(Cl)(=O)=O XTHDSFNKYHMRFZ-UHFFFAOYSA-N 0.000 description 1
- OFVKAIZITGCCDN-UHFFFAOYSA-N 2-fluoro-5-(trifluoromethyl)benzoyl chloride Chemical compound FC1=CC=C(C(F)(F)F)C=C1C(Cl)=O OFVKAIZITGCCDN-UHFFFAOYSA-N 0.000 description 1
- BODDMLVCYSGMOO-UHFFFAOYSA-N 2-fluoro-5-iodobenzenecarbothioyl chloride Chemical compound FC1=C(C(=S)Cl)C=C(C=C1)I BODDMLVCYSGMOO-UHFFFAOYSA-N 0.000 description 1
- OJLNQOQZULKEKC-UHFFFAOYSA-N 2-fluoro-5-iodobenzenesulfonyl chloride Chemical compound Fc1ccc(I)cc1S(Cl)(=O)=O OJLNQOQZULKEKC-UHFFFAOYSA-N 0.000 description 1
- CEMYZMDITJKYDA-UHFFFAOYSA-N 2-fluoro-5-iodobenzoyl chloride Chemical compound FC1=CC=C(I)C=C1C(Cl)=O CEMYZMDITJKYDA-UHFFFAOYSA-N 0.000 description 1
- GOAWUUQCRFPGFM-UHFFFAOYSA-N 2-fluoro-5-methylbenzenecarbothioyl chloride Chemical compound FC1=C(C(=S)Cl)C=C(C=C1)C GOAWUUQCRFPGFM-UHFFFAOYSA-N 0.000 description 1
- MOZTWWZAQLPJMT-UHFFFAOYSA-N 2-fluoro-5-methylbenzenesulfonyl chloride Chemical compound CC1=CC=C(F)C(S(Cl)(=O)=O)=C1 MOZTWWZAQLPJMT-UHFFFAOYSA-N 0.000 description 1
- WVRZOPWHCFDYSQ-UHFFFAOYSA-N 2-fluoro-5-methylbenzoyl chloride Chemical compound CC1=CC=C(F)C(C(Cl)=O)=C1 WVRZOPWHCFDYSQ-UHFFFAOYSA-N 0.000 description 1
- SJGKIULTSDRTCQ-UHFFFAOYSA-N 2-fluoro-5-nitrobenzenecarbothioyl chloride Chemical compound FC1=C(C(=S)Cl)C=C(C=C1)[N+](=O)[O-] SJGKIULTSDRTCQ-UHFFFAOYSA-N 0.000 description 1
- VQHGELUKJYOETQ-UHFFFAOYSA-N 2-fluoro-5-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=C(F)C(S(Cl)(=O)=O)=C1 VQHGELUKJYOETQ-UHFFFAOYSA-N 0.000 description 1
- SXJNRYPVXFTJOU-UHFFFAOYSA-N 2-fluoro-5-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(F)C(C(Cl)=O)=C1 SXJNRYPVXFTJOU-UHFFFAOYSA-N 0.000 description 1
- XTNSXNXWWXBOIU-UHFFFAOYSA-N 2-fluoro-6-(trifluoromethyl)benzenecarbothioyl chloride Chemical compound FC1=C(C(=S)Cl)C(=CC=C1)C(F)(F)F XTNSXNXWWXBOIU-UHFFFAOYSA-N 0.000 description 1
- VVCAQQGQZZLRJK-UHFFFAOYSA-N 2-fluoro-6-(trifluoromethyl)benzenesulfonyl chloride Chemical compound FC1=CC=CC(C(F)(F)F)=C1S(Cl)(=O)=O VVCAQQGQZZLRJK-UHFFFAOYSA-N 0.000 description 1
- ZDRYDSJMVRRAAF-UHFFFAOYSA-N 2-fluoro-6-(trifluoromethyl)benzoyl chloride Chemical compound FC1=CC=CC(C(F)(F)F)=C1C(Cl)=O ZDRYDSJMVRRAAF-UHFFFAOYSA-N 0.000 description 1
- PFVGZGZEFURWIE-UHFFFAOYSA-N 2-fluoro-6-iodobenzenecarbothioyl chloride Chemical compound FC1=C(C(=S)Cl)C(=CC=C1)I PFVGZGZEFURWIE-UHFFFAOYSA-N 0.000 description 1
- KUULKUHCAMRGCF-UHFFFAOYSA-N 2-fluoro-6-iodobenzoyl chloride Chemical compound FC1=CC=CC(I)=C1C(Cl)=O KUULKUHCAMRGCF-UHFFFAOYSA-N 0.000 description 1
- DFNGSFRCSOSDIX-UHFFFAOYSA-N 2-fluorobenzenecarbothioyl chloride Chemical compound FC1=C(C(=S)Cl)C=CC=C1 DFNGSFRCSOSDIX-UHFFFAOYSA-N 0.000 description 1
- ZSZKAQCISWFDCQ-UHFFFAOYSA-N 2-fluorobenzenesulfonyl chloride Chemical compound FC1=CC=CC=C1S(Cl)(=O)=O ZSZKAQCISWFDCQ-UHFFFAOYSA-N 0.000 description 1
- RAAGZOYMEQDCTD-UHFFFAOYSA-N 2-fluorobenzoyl chloride Chemical compound FC1=CC=CC=C1C(Cl)=O RAAGZOYMEQDCTD-UHFFFAOYSA-N 0.000 description 1
- 125000004791 2-fluoroethoxy group Chemical group FCCO* 0.000 description 1
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000006020 2-methyl-1-propenyl group Chemical group 0.000 description 1
- 125000006022 2-methyl-2-propenyl group Chemical group 0.000 description 1
- MEFNVSITOPKYCS-UHFFFAOYSA-N 2-octylnaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(CCCCCCCC)=CC=C21 MEFNVSITOPKYCS-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- HSEHKULCGSMHAE-UHFFFAOYSA-N 3,4,5-trifluorobenzenesulfonyl chloride Chemical compound FC1=CC(S(Cl)(=O)=O)=CC(F)=C1F HSEHKULCGSMHAE-UHFFFAOYSA-N 0.000 description 1
- YRUNCQNKZIQTEO-UHFFFAOYSA-N 3,4,5-trifluorobenzoyl chloride Chemical compound FC1=CC(C(Cl)=O)=CC(F)=C1F YRUNCQNKZIQTEO-UHFFFAOYSA-N 0.000 description 1
- 125000004361 3,4,5-trifluorophenyl group Chemical group [H]C1=C(F)C(F)=C(F)C([H])=C1* 0.000 description 1
- FSGLUBQENACWCC-UHFFFAOYSA-N 3,4-difluorobenzenesulfonyl chloride Chemical compound FC1=CC=C(S(Cl)(=O)=O)C=C1F FSGLUBQENACWCC-UHFFFAOYSA-N 0.000 description 1
- RPQWXGVZELKOEU-UHFFFAOYSA-N 3,4-difluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C=C1F RPQWXGVZELKOEU-UHFFFAOYSA-N 0.000 description 1
- BTRCVKADYDVSLI-UHFFFAOYSA-N 3,5-bis(trifluoromethyl)benzenesulfonyl chloride Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(S(Cl)(=O)=O)=C1 BTRCVKADYDVSLI-UHFFFAOYSA-N 0.000 description 1
- WAKMMQSMEDJRRI-UHFFFAOYSA-N 3,5-bis(trifluoromethyl)benzoyl chloride Chemical compound FC(F)(F)C1=CC(C(Cl)=O)=CC(C(F)(F)F)=C1 WAKMMQSMEDJRRI-UHFFFAOYSA-N 0.000 description 1
- ICRDZTRMUBACTH-UHFFFAOYSA-N 3,5-difluorobenzenecarbothioyl chloride Chemical compound FC=1C=C(C(=S)Cl)C=C(C=1)F ICRDZTRMUBACTH-UHFFFAOYSA-N 0.000 description 1
- IIQKIICAOXAXEJ-UHFFFAOYSA-N 3,5-difluorobenzenesulfonyl chloride Chemical compound FC1=CC(F)=CC(S(Cl)(=O)=O)=C1 IIQKIICAOXAXEJ-UHFFFAOYSA-N 0.000 description 1
- OYZWEOORLJBPMA-UHFFFAOYSA-N 3,5-difluorobenzoyl chloride Chemical compound FC1=CC(F)=CC(C(Cl)=O)=C1 OYZWEOORLJBPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 description 1
- DYVKHLGFIPFKMZ-UHFFFAOYSA-N 3,6-di(nonyl)naphthalene-1,8-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(CCCCCCCCC)=CC2=CC(CCCCCCCCC)=CC(S(O)(=O)=O)=C21 DYVKHLGFIPFKMZ-UHFFFAOYSA-N 0.000 description 1
- WOJDFUWWKJARLI-UHFFFAOYSA-N 3,6-di(nonyl)naphthalene-1-sulfonic acid Chemical compound OS(=O)(=O)C1=CC(CCCCCCCCC)=CC2=CC(CCCCCCCCC)=CC=C21 WOJDFUWWKJARLI-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- JCVDWIAVFOPBGX-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)propanal Chemical compound ClC1=CC=C(CCC=O)C(Cl)=C1 JCVDWIAVFOPBGX-UHFFFAOYSA-N 0.000 description 1
- NHCWIDIVEAKSAO-UHFFFAOYSA-N 3-(chloromethyl)-1,2,4,5-tetrafluorobenzene Chemical compound FC1=CC(F)=C(F)C(CCl)=C1F NHCWIDIVEAKSAO-UHFFFAOYSA-N 0.000 description 1
- ILHMMAZNAJPBDF-UHFFFAOYSA-N 3-(chloromethyl)-5-fluorobenzonitrile Chemical compound FC1=CC(CCl)=CC(C#N)=C1 ILHMMAZNAJPBDF-UHFFFAOYSA-N 0.000 description 1
- BFWSDVKKNDZYHA-UHFFFAOYSA-N 3-(trifluoromethyl)benzenecarbothioyl chloride Chemical compound FC(F)(F)C1=CC=CC(C(Cl)=S)=C1 BFWSDVKKNDZYHA-UHFFFAOYSA-N 0.000 description 1
- ONCAZCNPWWQQMW-UHFFFAOYSA-N 3-(trifluoromethyl)benzenesulfonyl chloride Chemical compound FC(F)(F)C1=CC=CC(S(Cl)(=O)=O)=C1 ONCAZCNPWWQQMW-UHFFFAOYSA-N 0.000 description 1
- RUJYJCANMOTJMO-UHFFFAOYSA-N 3-(trifluoromethyl)benzoyl chloride Chemical compound FC(F)(F)C1=CC=CC(C(Cl)=O)=C1 RUJYJCANMOTJMO-UHFFFAOYSA-N 0.000 description 1
- HSJRFLZQNKYQGS-UHFFFAOYSA-N 3-[9,9-bis(4-nitrophenyl)-7-(9-phenylcarbazol-3-yl)fluoren-2-yl]-9-phenylcarbazole Chemical compound [O-][N+](=O)c1ccc(cc1)C1(c2cc(ccc2-c2ccc(cc12)-c1ccc2n(-c3ccccc3)c3ccccc3c2c1)-c1ccc2n(-c3ccccc3)c3ccccc3c2c1)c1ccc(cc1)[N+]([O-])=O HSJRFLZQNKYQGS-UHFFFAOYSA-N 0.000 description 1
- GRTHDDIILOWDFI-UHFFFAOYSA-N 3-bromo-2-fluorobenzenecarbothioyl chloride Chemical compound BrC=1C(=C(C(=S)Cl)C=CC=1)F GRTHDDIILOWDFI-UHFFFAOYSA-N 0.000 description 1
- HCIVRVSTKMVMGM-UHFFFAOYSA-N 3-bromo-2-fluorobenzenesulfonyl chloride Chemical compound FC1=C(Br)C=CC=C1S(Cl)(=O)=O HCIVRVSTKMVMGM-UHFFFAOYSA-N 0.000 description 1
- MCRKBWVSQZTERQ-UHFFFAOYSA-N 3-bromo-2-fluorobenzoyl chloride Chemical compound FC1=C(Br)C=CC=C1C(Cl)=O MCRKBWVSQZTERQ-UHFFFAOYSA-N 0.000 description 1
- QXBFGUDNYBXRLI-UHFFFAOYSA-N 3-bromo-4-fluorobenzenecarbothioyl chloride Chemical compound BrC=1C=C(C(=S)Cl)C=CC=1F QXBFGUDNYBXRLI-UHFFFAOYSA-N 0.000 description 1
- BEEHKBVVTWJSRH-UHFFFAOYSA-N 3-bromo-4-fluorobenzenesulfonyl chloride Chemical compound FC1=CC=C(S(Cl)(=O)=O)C=C1Br BEEHKBVVTWJSRH-UHFFFAOYSA-N 0.000 description 1
- HPHZOCIBMCWXCQ-UHFFFAOYSA-N 3-bromo-4-fluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C=C1Br HPHZOCIBMCWXCQ-UHFFFAOYSA-N 0.000 description 1
- AHWDOTRRKSFOEA-UHFFFAOYSA-N 3-bromo-5-fluorobenzenecarbothioyl chloride Chemical compound BrC=1C=C(C(=S)Cl)C=C(C=1)F AHWDOTRRKSFOEA-UHFFFAOYSA-N 0.000 description 1
- HZJBQCUMWMMHMK-UHFFFAOYSA-N 3-bromo-5-fluorobenzenesulfonyl chloride Chemical compound FC1=CC(Br)=CC(S(Cl)(=O)=O)=C1 HZJBQCUMWMMHMK-UHFFFAOYSA-N 0.000 description 1
- RGMMCYNLNAUIJX-UHFFFAOYSA-N 3-bromo-5-fluorobenzoyl chloride Chemical compound FC1=CC(Br)=CC(C(Cl)=O)=C1 RGMMCYNLNAUIJX-UHFFFAOYSA-N 0.000 description 1
- PPYLXLRXJABZCN-UHFFFAOYSA-N 3-chloro-2-fluorobenzenecarbothioyl chloride Chemical compound ClC=1C(=C(C(=S)Cl)C=CC=1)F PPYLXLRXJABZCN-UHFFFAOYSA-N 0.000 description 1
- LIRQNYQIFFLGIE-UHFFFAOYSA-N 3-chloro-2-fluorobenzenesulfonyl chloride Chemical compound FC1=C(Cl)C=CC=C1S(Cl)(=O)=O LIRQNYQIFFLGIE-UHFFFAOYSA-N 0.000 description 1
- VBYJOUAMJITBNL-UHFFFAOYSA-N 3-chloro-2-fluorobenzoyl chloride Chemical compound FC1=C(Cl)C=CC=C1C(Cl)=O VBYJOUAMJITBNL-UHFFFAOYSA-N 0.000 description 1
- YGVCPTTYFRDYRZ-UHFFFAOYSA-N 3-chloro-4-fluorobenzenecarbothioyl chloride Chemical compound ClC=1C=C(C(=S)Cl)C=CC=1F YGVCPTTYFRDYRZ-UHFFFAOYSA-N 0.000 description 1
- DXFXNSNBZNELII-UHFFFAOYSA-N 3-chloro-4-fluorobenzenesulfonyl chloride Chemical compound FC1=CC=C(S(Cl)(=O)=O)C=C1Cl DXFXNSNBZNELII-UHFFFAOYSA-N 0.000 description 1
- DLZUHSFUBZTBQZ-UHFFFAOYSA-N 3-chloro-4-fluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C=C1Cl DLZUHSFUBZTBQZ-UHFFFAOYSA-N 0.000 description 1
- VFSQCTZAXPWXDF-UHFFFAOYSA-N 3-chloro-5-fluorobenzenecarbothioyl chloride Chemical compound ClC=1C=C(C(=S)Cl)C=C(C=1)F VFSQCTZAXPWXDF-UHFFFAOYSA-N 0.000 description 1
- DMJUAPPEXOKHSW-UHFFFAOYSA-N 3-chloro-5-fluorobenzenesulfonyl chloride Chemical compound FC1=CC(Cl)=CC(S(Cl)(=O)=O)=C1 DMJUAPPEXOKHSW-UHFFFAOYSA-N 0.000 description 1
- CQQPZYVMGWYJOO-UHFFFAOYSA-N 3-chloro-5-fluorobenzoyl chloride Chemical compound FC1=CC(Cl)=CC(C(Cl)=O)=C1 CQQPZYVMGWYJOO-UHFFFAOYSA-N 0.000 description 1
- YYKFOAVIBLQADJ-UHFFFAOYSA-N 3-cyano-5-fluorobenzenecarbothioyl chloride Chemical compound C(#N)C=1C=C(C(=S)Cl)C=C(C=1)F YYKFOAVIBLQADJ-UHFFFAOYSA-N 0.000 description 1
- ZQEROTOETXELJU-UHFFFAOYSA-N 3-cyano-5-fluorobenzenesulfonyl chloride Chemical compound FC1=CC(C#N)=CC(S(Cl)(=O)=O)=C1 ZQEROTOETXELJU-UHFFFAOYSA-N 0.000 description 1
- WLBLIJUBANCKOH-UHFFFAOYSA-N 3-cyano-5-fluorobenzoyl chloride Chemical compound FC1=CC(C#N)=CC(C(Cl)=O)=C1 WLBLIJUBANCKOH-UHFFFAOYSA-N 0.000 description 1
- DZYOZGWKVUJSSR-UHFFFAOYSA-N 3-fluoro-2-nitrobenzenecarbothioyl chloride Chemical compound FC=1C(=C(C(=S)Cl)C=CC=1)[N+](=O)[O-] DZYOZGWKVUJSSR-UHFFFAOYSA-N 0.000 description 1
- DKFATVSJDGJDQW-UHFFFAOYSA-N 3-fluoro-2-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=C(F)C=CC=C1S(Cl)(=O)=O DKFATVSJDGJDQW-UHFFFAOYSA-N 0.000 description 1
- VVFRPFIZSXRDJH-UHFFFAOYSA-N 3-fluoro-2-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=C(F)C=CC=C1C(Cl)=O VVFRPFIZSXRDJH-UHFFFAOYSA-N 0.000 description 1
- VDNRXCYMWBORTO-UHFFFAOYSA-N 3-fluoro-4-(trifluoromethyl)benzenecarbothioyl chloride Chemical compound FC=1C=C(C(=S)Cl)C=CC=1C(F)(F)F VDNRXCYMWBORTO-UHFFFAOYSA-N 0.000 description 1
- OWOFQIUPVZIKSH-UHFFFAOYSA-N 3-fluoro-4-(trifluoromethyl)benzenesulfonyl chloride Chemical compound FC1=CC(S(Cl)(=O)=O)=CC=C1C(F)(F)F OWOFQIUPVZIKSH-UHFFFAOYSA-N 0.000 description 1
- DPDAEMNQJYDHRQ-UHFFFAOYSA-N 3-fluoro-4-(trifluoromethyl)benzoyl chloride Chemical compound FC1=CC(C(Cl)=O)=CC=C1C(F)(F)F DPDAEMNQJYDHRQ-UHFFFAOYSA-N 0.000 description 1
- YECZXXCHFMSPRD-UHFFFAOYSA-N 3-fluoro-4-methylbenzenecarbothioyl chloride Chemical compound FC=1C=C(C(=S)Cl)C=CC=1C YECZXXCHFMSPRD-UHFFFAOYSA-N 0.000 description 1
- YDUHIMCRFRIVFI-UHFFFAOYSA-N 3-fluoro-4-methylbenzenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1F YDUHIMCRFRIVFI-UHFFFAOYSA-N 0.000 description 1
- DPWCZSXNEGNALT-UHFFFAOYSA-N 3-fluoro-4-methylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1F DPWCZSXNEGNALT-UHFFFAOYSA-N 0.000 description 1
- CRMXFTUJPYDCNY-UHFFFAOYSA-N 3-fluoro-4-nitrobenzenecarbothioyl chloride Chemical compound FC=1C=C(C(=S)Cl)C=CC=1[N+](=O)[O-] CRMXFTUJPYDCNY-UHFFFAOYSA-N 0.000 description 1
- AAWFUSFNPBRQDE-UHFFFAOYSA-N 3-fluoro-4-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=C(S(Cl)(=O)=O)C=C1F AAWFUSFNPBRQDE-UHFFFAOYSA-N 0.000 description 1
- DPAMLESDGWVDBW-UHFFFAOYSA-N 3-fluoro-4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1F DPAMLESDGWVDBW-UHFFFAOYSA-N 0.000 description 1
- FUDNPJYHGCLHEO-UHFFFAOYSA-N 3-fluoro-5-(trifluoromethyl)benzenecarbothioyl chloride Chemical compound FC=1C=C(C(=S)Cl)C=C(C=1)C(F)(F)F FUDNPJYHGCLHEO-UHFFFAOYSA-N 0.000 description 1
- LANWEGQCPRKLAI-UHFFFAOYSA-N 3-fluoro-5-(trifluoromethyl)benzenesulfonyl chloride Chemical compound FC1=CC(C(F)(F)F)=CC(S(Cl)(=O)=O)=C1 LANWEGQCPRKLAI-UHFFFAOYSA-N 0.000 description 1
- BGAKSLBTFLVNAH-UHFFFAOYSA-N 3-fluoro-5-(trifluoromethyl)benzoyl chloride Chemical compound FC1=CC(C(Cl)=O)=CC(C(F)(F)F)=C1 BGAKSLBTFLVNAH-UHFFFAOYSA-N 0.000 description 1
- HGRGTBUWPVKXEW-UHFFFAOYSA-N 3-fluorobenzenecarbothioyl chloride Chemical compound FC=1C=C(C(=S)Cl)C=CC=1 HGRGTBUWPVKXEW-UHFFFAOYSA-N 0.000 description 1
- OKYSUJVCDXZGKE-UHFFFAOYSA-N 3-fluorobenzenesulfonyl chloride Chemical compound FC1=CC=CC(S(Cl)(=O)=O)=C1 OKYSUJVCDXZGKE-UHFFFAOYSA-N 0.000 description 1
- SYVNVEGIRVXRQH-UHFFFAOYSA-N 3-fluorobenzoyl chloride Chemical compound FC1=CC=CC(C(Cl)=O)=C1 SYVNVEGIRVXRQH-UHFFFAOYSA-N 0.000 description 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- AWVCSOPYZNBXLK-UHFFFAOYSA-N 4-(1,1,2,2,2-pentafluoroethyl)benzenecarbothioyl chloride Chemical compound FC(C(F)(F)F)(C1=CC=C(C(=S)Cl)C=C1)F AWVCSOPYZNBXLK-UHFFFAOYSA-N 0.000 description 1
- VTGRVYJPIVZZGS-UHFFFAOYSA-N 4-(chloromethyl)-1,2-difluorobenzene Chemical compound FC1=CC=C(CCl)C=C1F VTGRVYJPIVZZGS-UHFFFAOYSA-N 0.000 description 1
- NKYBHYJCRWYNTJ-UHFFFAOYSA-N 4-(chloromethyl)-1-ethoxy-2-(trifluoromethyl)benzene Chemical compound CCOC1=CC=C(CCl)C=C1C(F)(F)F NKYBHYJCRWYNTJ-UHFFFAOYSA-N 0.000 description 1
- LSKZGATXKOIZNR-UHFFFAOYSA-N 4-(chloromethyl)-1-fluoro-2-(trifluoromethyl)benzene Chemical compound FC1=CC=C(CCl)C=C1C(F)(F)F LSKZGATXKOIZNR-UHFFFAOYSA-N 0.000 description 1
- SDAPHOYTPICABO-UHFFFAOYSA-N 4-(chloromethyl)-1-fluoro-2-methylbenzene Chemical compound CC1=CC(CCl)=CC=C1F SDAPHOYTPICABO-UHFFFAOYSA-N 0.000 description 1
- ZEANBUCPNMDYES-UHFFFAOYSA-N 4-(chloromethyl)-1-fluoro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(CCl)=CC=C1F ZEANBUCPNMDYES-UHFFFAOYSA-N 0.000 description 1
- LBRMEGUZSFQNIT-UHFFFAOYSA-N 4-(chloromethyl)-2-fluoro-1-(trifluoromethyl)benzene Chemical compound FC1=CC(CCl)=CC=C1C(F)(F)F LBRMEGUZSFQNIT-UHFFFAOYSA-N 0.000 description 1
- CDFRDDZQCBOCGF-UHFFFAOYSA-N 4-(chloromethyl)-2-fluoro-1-methylbenzene Chemical compound CC1=CC=C(CCl)C=C1F CDFRDDZQCBOCGF-UHFFFAOYSA-N 0.000 description 1
- OBWIVHSCVRIOAA-UHFFFAOYSA-N 4-(chloromethyl)-2-fluoro-1-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(CCl)C=C1F OBWIVHSCVRIOAA-UHFFFAOYSA-N 0.000 description 1
- HBJIJFADGURZGI-UHFFFAOYSA-N 4-(chloromethyl)-3-fluorobenzonitrile Chemical compound FC1=CC(C#N)=CC=C1CCl HBJIJFADGURZGI-UHFFFAOYSA-N 0.000 description 1
- OXZYBOLWRXENKT-UHFFFAOYSA-N 4-(trifluoromethyl)benzoyl chloride Chemical compound FC(F)(F)C1=CC=C(C(Cl)=O)C=C1 OXZYBOLWRXENKT-UHFFFAOYSA-N 0.000 description 1
- BCMFTOCCLOAGBP-UHFFFAOYSA-N 4-(trifluoromethylsulfanyl)benzoyl chloride Chemical compound FC(F)(F)SC1=CC=C(C(Cl)=O)C=C1 BCMFTOCCLOAGBP-UHFFFAOYSA-N 0.000 description 1
- IQQKLDUOACMTHC-UHFFFAOYSA-N 4-[9,9-bis(4-nitrophenyl)-7-[4-(N-phenylanilino)phenyl]fluoren-2-yl]-N,N-diphenylaniline Chemical compound [O-][N+](=O)c1ccc(cc1)C1(c2cc(ccc2-c2ccc(cc12)-c1ccc(cc1)N(c1ccccc1)c1ccccc1)-c1ccc(cc1)N(c1ccccc1)c1ccccc1)c1ccc(cc1)[N+]([O-])=O IQQKLDUOACMTHC-UHFFFAOYSA-N 0.000 description 1
- OMMDKWKADHHWIB-UHFFFAOYSA-N 4-[9-(4-aminophenyl)-2,7-bis(3-carbazol-9-ylphenyl)fluoren-9-yl]aniline Chemical compound Nc1ccc(cc1)C1(c2cc(ccc2-c2ccc(cc12)-c1cccc(c1)-n1c2ccccc2c2ccccc12)-c1cccc(c1)-n1c2ccccc2c2ccccc12)c1ccc(N)cc1 OMMDKWKADHHWIB-UHFFFAOYSA-N 0.000 description 1
- GNGIOQVWZPAHPF-UHFFFAOYSA-N 4-[9-(4-aminophenyl)-2,7-bis(9-phenylcarbazol-3-yl)fluoren-9-yl]aniline Chemical compound Nc1ccc(cc1)C1(c2cc(ccc2-c2ccc(cc12)-c1ccc2n(-c3ccccc3)c3ccccc3c2c1)-c1ccc2n(-c3ccccc3)c3ccccc3c2c1)c1ccc(N)cc1 GNGIOQVWZPAHPF-UHFFFAOYSA-N 0.000 description 1
- UDKQGFMDBMYVHI-UHFFFAOYSA-N 4-bromo-1-(chloromethyl)-2-fluorobenzene Chemical compound FC1=CC(Br)=CC=C1CCl UDKQGFMDBMYVHI-UHFFFAOYSA-N 0.000 description 1
- JKXAKUDNMINKEU-UHFFFAOYSA-N 4-bromo-2-(chloromethyl)-1-fluorobenzene Chemical compound FC1=CC=C(Br)C=C1CCl JKXAKUDNMINKEU-UHFFFAOYSA-N 0.000 description 1
- JOPVKLRKFIPVHT-UHFFFAOYSA-N 4-bromo-2-fluorobenzenecarbothioyl chloride Chemical compound BrC1=CC(=C(C(=S)Cl)C=C1)F JOPVKLRKFIPVHT-UHFFFAOYSA-N 0.000 description 1
- PCFIABOQFAFDAU-UHFFFAOYSA-N 4-bromo-2-fluorobenzoyl chloride Chemical compound FC1=CC(Br)=CC=C1C(Cl)=O PCFIABOQFAFDAU-UHFFFAOYSA-N 0.000 description 1
- ZDAGIAOHMSXWES-UHFFFAOYSA-N 4-chloro-2,4-difluorocyclohexa-1,5-diene-1-sulfonyl chloride Chemical compound ClC1(CC(=C(C=C1)S(=O)(=O)Cl)F)F ZDAGIAOHMSXWES-UHFFFAOYSA-N 0.000 description 1
- SRVZHRWUBAEOID-UHFFFAOYSA-N 4-chloro-2-(chloromethyl)-1-fluorobenzene Chemical compound FC1=CC=C(Cl)C=C1CCl SRVZHRWUBAEOID-UHFFFAOYSA-N 0.000 description 1
- XCLZEDMAWGTLTL-UHFFFAOYSA-N 4-chloro-2-fluorobenzenecarbothioyl chloride Chemical compound ClC1=CC(=C(C(=S)Cl)C=C1)F XCLZEDMAWGTLTL-UHFFFAOYSA-N 0.000 description 1
- ZFZRENUEJCOCRE-UHFFFAOYSA-N 4-chloro-2-fluorobenzenesulfonyl chloride Chemical compound FC1=CC(Cl)=CC=C1S(Cl)(=O)=O ZFZRENUEJCOCRE-UHFFFAOYSA-N 0.000 description 1
- PWHFJLCMUCFYRQ-UHFFFAOYSA-N 4-chloro-2-fluorobenzoyl chloride Chemical compound FC1=CC(Cl)=CC=C1C(Cl)=O PWHFJLCMUCFYRQ-UHFFFAOYSA-N 0.000 description 1
- OPCGEDQNSSCKIB-UHFFFAOYSA-N 4-cyano-2-fluorobenzenecarbothioyl chloride Chemical compound C(#N)C1=CC(=C(C(=S)Cl)C=C1)F OPCGEDQNSSCKIB-UHFFFAOYSA-N 0.000 description 1
- UYHVZXCIAQVHMY-UHFFFAOYSA-N 4-cyano-2-fluorobenzenesulfonyl chloride Chemical compound FC1=CC(C#N)=CC=C1S(Cl)(=O)=O UYHVZXCIAQVHMY-UHFFFAOYSA-N 0.000 description 1
- WUFOPFHPVDSXHL-UHFFFAOYSA-N 4-cyano-2-fluorobenzoyl chloride Chemical compound FC1=CC(C#N)=CC=C1C(Cl)=O WUFOPFHPVDSXHL-UHFFFAOYSA-N 0.000 description 1
- KWXICGTUELOLSQ-UHFFFAOYSA-N 4-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=C(S(O)(=O)=O)C=C1 KWXICGTUELOLSQ-UHFFFAOYSA-N 0.000 description 1
- MAGFQRLKWCCTQJ-UHFFFAOYSA-N 4-ethenylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-N 0.000 description 1
- ADLODKVKPPSQON-UHFFFAOYSA-N 4-ethoxy-3-(trifluoromethyl)benzenecarbothioyl chloride Chemical compound FC(C=1C=C(C(=S)Cl)C=CC=1OCC)(F)F ADLODKVKPPSQON-UHFFFAOYSA-N 0.000 description 1
- AONSXOZROQCKGE-UHFFFAOYSA-N 4-ethoxy-3-(trifluoromethyl)benzenesulfonyl chloride 4-(trifluoromethyl)benzenesulfonyl chloride Chemical compound FC(C=1C=C(C=CC1OCC)S(=O)(=O)Cl)(F)F.FC(C1=CC=C(C=C1)S(=O)(=O)Cl)(F)F AONSXOZROQCKGE-UHFFFAOYSA-N 0.000 description 1
- CSVLARKLTDXMQD-UHFFFAOYSA-N 4-ethoxy-3-(trifluoromethyl)benzoyl chloride Chemical compound CCOC1=CC=C(C(Cl)=O)C=C1C(F)(F)F CSVLARKLTDXMQD-UHFFFAOYSA-N 0.000 description 1
- QZGOTHKUMRGXRD-UHFFFAOYSA-N 4-fluoro-2-(trifluoromethyl)benzenecarbothioyl chloride Chemical compound FC1=CC(=C(C(=S)Cl)C=C1)C(F)(F)F QZGOTHKUMRGXRD-UHFFFAOYSA-N 0.000 description 1
- IGMYEVQPXWKFQF-UHFFFAOYSA-N 4-fluoro-2-(trifluoromethyl)benzenesulfonyl chloride Chemical compound FC1=CC=C(S(Cl)(=O)=O)C(C(F)(F)F)=C1 IGMYEVQPXWKFQF-UHFFFAOYSA-N 0.000 description 1
- OEYHURRIOWWRMD-UHFFFAOYSA-N 4-fluoro-2-(trifluoromethyl)benzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C(C(F)(F)F)=C1 OEYHURRIOWWRMD-UHFFFAOYSA-N 0.000 description 1
- YNWRIKZMSVBXPJ-UHFFFAOYSA-N 4-fluoro-2-methylbenzenecarbothioyl chloride Chemical compound FC1=CC(=C(C(=S)Cl)C=C1)C YNWRIKZMSVBXPJ-UHFFFAOYSA-N 0.000 description 1
- XLPGWKNCWMFHOD-UHFFFAOYSA-N 4-fluoro-2-methylbenzenesulfonyl chloride Chemical compound CC1=CC(F)=CC=C1S(Cl)(=O)=O XLPGWKNCWMFHOD-UHFFFAOYSA-N 0.000 description 1
- KZUXJRQQHJREGH-UHFFFAOYSA-N 4-fluoro-2-methylbenzoyl chloride Chemical compound CC1=CC(F)=CC=C1C(Cl)=O KZUXJRQQHJREGH-UHFFFAOYSA-N 0.000 description 1
- VOEOWFCEKNJITD-UHFFFAOYSA-N 4-fluoro-2-nitrobenzenecarbothioyl chloride Chemical compound FC1=CC(=C(C(=S)Cl)C=C1)[N+](=O)[O-] VOEOWFCEKNJITD-UHFFFAOYSA-N 0.000 description 1
- BHSUAEKACYUVJP-UHFFFAOYSA-N 4-fluoro-2-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC(F)=CC=C1S(Cl)(=O)=O BHSUAEKACYUVJP-UHFFFAOYSA-N 0.000 description 1
- NQMGZEFEQXWOAT-UHFFFAOYSA-N 4-fluoro-2-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC(F)=CC=C1C(Cl)=O NQMGZEFEQXWOAT-UHFFFAOYSA-N 0.000 description 1
- WYIOURBYVHZNJD-UHFFFAOYSA-N 4-fluoro-3-(trifluoromethyl)benzenecarbothioyl chloride Chemical compound FC1=C(C=C(C(=S)Cl)C=C1)C(F)(F)F WYIOURBYVHZNJD-UHFFFAOYSA-N 0.000 description 1
- AYOKQWBPSUHEQU-UHFFFAOYSA-N 4-fluoro-3-(trifluoromethyl)benzenesulfonyl chloride Chemical compound FC1=CC=C(S(Cl)(=O)=O)C=C1C(F)(F)F AYOKQWBPSUHEQU-UHFFFAOYSA-N 0.000 description 1
- BUDISZQHCHGLJW-UHFFFAOYSA-N 4-fluoro-3-(trifluoromethyl)benzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C=C1C(F)(F)F BUDISZQHCHGLJW-UHFFFAOYSA-N 0.000 description 1
- GDVQMAMFBNZEBX-UHFFFAOYSA-N 4-fluoro-3-methylbenzenecarbothioyl chloride Chemical compound FC1=C(C=C(C(=S)Cl)C=C1)C GDVQMAMFBNZEBX-UHFFFAOYSA-N 0.000 description 1
- ALEQALYEZFNWOP-UHFFFAOYSA-N 4-fluoro-3-methylbenzenesulfonyl chloride Chemical compound CC1=CC(S(Cl)(=O)=O)=CC=C1F ALEQALYEZFNWOP-UHFFFAOYSA-N 0.000 description 1
- FMFLKTDRPXYUGP-UHFFFAOYSA-N 4-fluoro-3-methylbenzoyl chloride Chemical compound CC1=CC(C(Cl)=O)=CC=C1F FMFLKTDRPXYUGP-UHFFFAOYSA-N 0.000 description 1
- OZFQRIOIRFPCFZ-UHFFFAOYSA-N 4-fluoro-3-nitrobenzenecarbothioyl chloride Chemical compound FC1=C(C=C(C(=S)Cl)C=C1)[N+](=O)[O-] OZFQRIOIRFPCFZ-UHFFFAOYSA-N 0.000 description 1
- OJNVFOHHRJZBEG-UHFFFAOYSA-N 4-fluoro-3-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC(C(Cl)=O)=CC=C1F OJNVFOHHRJZBEG-UHFFFAOYSA-N 0.000 description 1
- BTMTUIFKQHQAPP-UHFFFAOYSA-N 4-fluorobenzenecarbothioyl chloride Chemical compound FC1=CC=C(C(Cl)=S)C=C1 BTMTUIFKQHQAPP-UHFFFAOYSA-N 0.000 description 1
- BFXHJFKKRGVUMU-UHFFFAOYSA-N 4-fluorobenzenesulfonyl chloride Chemical compound FC1=CC=C(S(Cl)(=O)=O)C=C1 BFXHJFKKRGVUMU-UHFFFAOYSA-N 0.000 description 1
- CZKLEJHVLCMVQR-UHFFFAOYSA-N 4-fluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C=C1 CZKLEJHVLCMVQR-UHFFFAOYSA-N 0.000 description 1
- ICTSJDQTIQLGSE-UHFFFAOYSA-N 4-hexylnaphthalene-1-sulfonic acid Chemical compound CCCCCCc1ccc(c2ccccc12)S(O)(=O)=O ICTSJDQTIQLGSE-UHFFFAOYSA-N 0.000 description 1
- FEPBITJSIHRMRT-UHFFFAOYSA-N 4-hydroxybenzenesulfonic acid Chemical compound OC1=CC=C(S(O)(=O)=O)C=C1 FEPBITJSIHRMRT-UHFFFAOYSA-N 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- ALUFGPFDDJIQCW-UHFFFAOYSA-N 5-(chloromethyl)-1,2,3-trifluorobenzene Chemical compound FC1=CC(CCl)=CC(F)=C1F ALUFGPFDDJIQCW-UHFFFAOYSA-N 0.000 description 1
- LVDUMVTYQQNAEQ-UHFFFAOYSA-N 5-bromo-2-fluorobenzenecarbothioyl chloride Chemical compound BrC=1C=CC(=C(C(=S)Cl)C=1)F LVDUMVTYQQNAEQ-UHFFFAOYSA-N 0.000 description 1
- LLDLTDWAHZBZIQ-UHFFFAOYSA-N 5-bromo-2-fluorobenzenesulfonyl chloride Chemical compound FC1=CC=C(Br)C=C1S(Cl)(=O)=O LLDLTDWAHZBZIQ-UHFFFAOYSA-N 0.000 description 1
- LEGBISULKASFCD-UHFFFAOYSA-N 5-bromo-2-fluorobenzoyl chloride Chemical compound FC1=CC=C(Br)C=C1C(Cl)=O LEGBISULKASFCD-UHFFFAOYSA-N 0.000 description 1
- IGRQLROCYOHBDF-UHFFFAOYSA-N 5-chloro-2-(chloromethyl)-1,5-difluorocyclohexa-1,3-diene Chemical compound ClC1(CC(=C(CCl)C=C1)F)F IGRQLROCYOHBDF-UHFFFAOYSA-N 0.000 description 1
- CCCRDACDUNRZHT-UHFFFAOYSA-N 5-chloro-2-fluorobenzenecarbothioyl chloride Chemical compound ClC=1C=CC(=C(C(=S)Cl)C=1)F CCCRDACDUNRZHT-UHFFFAOYSA-N 0.000 description 1
- OZKAHSNNKADHTK-UHFFFAOYSA-N 5-chloro-2-fluorobenzenesulfonyl chloride Chemical compound FC1=CC=C(Cl)C=C1S(Cl)(=O)=O OZKAHSNNKADHTK-UHFFFAOYSA-N 0.000 description 1
- VWGAATKTEAKOCO-UHFFFAOYSA-N 5-chloro-2-fluorobenzoyl chloride Chemical compound FC1=CC=C(Cl)C=C1C(Cl)=O VWGAATKTEAKOCO-UHFFFAOYSA-N 0.000 description 1
- HJIXUBUSVPDLTK-UHFFFAOYSA-N 5-fluoro-2-(trifluoromethyl)benzenecarbothioyl chloride Chemical compound FC=1C=C(C(=S)Cl)C(=CC=1)C(F)(F)F HJIXUBUSVPDLTK-UHFFFAOYSA-N 0.000 description 1
- DRXFNKKEESCKSG-UHFFFAOYSA-N 5-fluoro-2-(trifluoromethyl)benzenesulfonyl chloride Chemical compound FC1=CC=C(C(F)(F)F)C(S(Cl)(=O)=O)=C1 DRXFNKKEESCKSG-UHFFFAOYSA-N 0.000 description 1
- VHTVVTDYYXQDHS-UHFFFAOYSA-N 5-fluoro-2-(trifluoromethyl)benzoyl chloride Chemical compound FC1=CC=C(C(F)(F)F)C(C(Cl)=O)=C1 VHTVVTDYYXQDHS-UHFFFAOYSA-N 0.000 description 1
- ZYHCGKSWXBYCRA-UHFFFAOYSA-N 5-fluoro-2-methylbenzenecarbothioyl chloride Chemical compound FC=1C=C(C(=S)Cl)C(=CC=1)C ZYHCGKSWXBYCRA-UHFFFAOYSA-N 0.000 description 1
- NPEWBMJAUUSBLE-UHFFFAOYSA-N 5-fluoro-2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=C(F)C=C1S(Cl)(=O)=O NPEWBMJAUUSBLE-UHFFFAOYSA-N 0.000 description 1
- HBAQRSDZSVESSF-UHFFFAOYSA-N 5-fluoro-2-methylbenzoyl chloride Chemical compound CC1=CC=C(F)C=C1C(Cl)=O HBAQRSDZSVESSF-UHFFFAOYSA-N 0.000 description 1
- YIASFJKYSZBYIU-UHFFFAOYSA-N 5-fluoro-2-nitrobenzenecarbothioyl chloride Chemical compound FC=1C=C(C(=S)Cl)C(=CC=1)[N+](=O)[O-] YIASFJKYSZBYIU-UHFFFAOYSA-N 0.000 description 1
- ALKFOTRKZGCLFU-UHFFFAOYSA-N 5-fluoro-2-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1S(Cl)(=O)=O ALKFOTRKZGCLFU-UHFFFAOYSA-N 0.000 description 1
- DHNJQRSDZABGBP-UHFFFAOYSA-N 5-fluoro-2-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1C(Cl)=O DHNJQRSDZABGBP-UHFFFAOYSA-N 0.000 description 1
- YCPXWRQRBFJBPZ-UHFFFAOYSA-N 5-sulfosalicylic acid Chemical compound OC(=O)C1=CC(S(O)(=O)=O)=CC=C1O YCPXWRQRBFJBPZ-UHFFFAOYSA-N 0.000 description 1
- MPMSFLAIOPUDMV-UHFFFAOYSA-N 7-aminonaphthalene-1,3-disulfonic acid;sodium Chemical compound [Na].[Na].C1=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=CC(N)=CC=C21 MPMSFLAIOPUDMV-UHFFFAOYSA-N 0.000 description 1
- NWWWPDGERSVSBP-UHFFFAOYSA-N 9-phenyl-3-[7-(9-phenylcarbazol-3-yl)-9H-fluoren-2-yl]carbazole Chemical compound C1c2cc(ccc2-c2ccc(cc12)-c1ccc2n(-c3ccccc3)c3ccccc3c2c1)-c1ccc2n(-c3ccccc3)c3ccccc3c2c1 NWWWPDGERSVSBP-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229910021630 Antimony pentafluoride Inorganic materials 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- OZSKVOSOFGFJQO-UHFFFAOYSA-N BrC1=C(C(=S)Cl)C=CC=C1F.BrC1=C(C(=S)Cl)C(=CC=C1)F Chemical compound BrC1=C(C(=S)Cl)C=CC=C1F.BrC1=C(C(=S)Cl)C(=CC=C1)F OZSKVOSOFGFJQO-UHFFFAOYSA-N 0.000 description 1
- GYSVKTSICZEFDI-UHFFFAOYSA-N BrC=1C=C(CCl)C=C(C1)F.BrC=1C=C(CCl)C=CC1F Chemical compound BrC=1C=C(CCl)C=C(C1)F.BrC=1C=C(CCl)C=CC1F GYSVKTSICZEFDI-UHFFFAOYSA-N 0.000 description 1
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 description 1
- 125000005915 C6-C14 aryl group Chemical group 0.000 description 1
- UDYCQCSHSJLKFG-UHFFFAOYSA-N CCCCCCCCCCCCc1cc2ccccc2cc1S(O)(=O)=O Chemical compound CCCCCCCCCCCCc1cc2ccccc2cc1S(O)(=O)=O UDYCQCSHSJLKFG-UHFFFAOYSA-N 0.000 description 1
- XPQOEOAEOZRAIS-UHFFFAOYSA-N CCCCCCc1ccc(CCCCCC)c(c1)S(O)(=O)=O Chemical compound CCCCCCc1ccc(CCCCCC)c(c1)S(O)(=O)=O XPQOEOAEOZRAIS-UHFFFAOYSA-N 0.000 description 1
- ZINICSCDQVBRJU-UHFFFAOYSA-N CCCCCCc1ccc2cc(ccc2c1)S(O)(=O)=O Chemical compound CCCCCCc1ccc2cc(ccc2c1)S(O)(=O)=O ZINICSCDQVBRJU-UHFFFAOYSA-N 0.000 description 1
- MYKHUARBDBEWFH-UHFFFAOYSA-N CCCCCCc1ccc2cccc(c2c1)S(O)(=O)=O Chemical compound CCCCCCc1ccc2cccc(c2c1)S(O)(=O)=O MYKHUARBDBEWFH-UHFFFAOYSA-N 0.000 description 1
- JYAVIPNDJHQFON-UHFFFAOYSA-N CCCCc1cc2ccc(cc2cc1CCCC)S(O)(=O)=O Chemical compound CCCCc1cc2ccc(cc2cc1CCCC)S(O)(=O)=O JYAVIPNDJHQFON-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- ZVZRXZQPLPKTRB-UHFFFAOYSA-N ClC1=CC(=C(C=C1)NC(=S)Cl)F Chemical compound ClC1=CC(=C(C=C1)NC(=S)Cl)F ZVZRXZQPLPKTRB-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- JVEZBJSPAQQIMK-UHFFFAOYSA-N FC(C(F)(F)F)(C1=CC=C(C(=O)Cl)C=C1)F Chemical compound FC(C(F)(F)F)(C1=CC=C(C(=O)Cl)C=C1)F JVEZBJSPAQQIMK-UHFFFAOYSA-N 0.000 description 1
- AVAIQPJKRMLGGR-UHFFFAOYSA-N FC1=C(C(=CC(=C1)F)F)NC(=S)Cl.FC1=C(C=C(C(=C1)F)F)NC(=S)Cl Chemical compound FC1=C(C(=CC(=C1)F)F)NC(=S)Cl.FC1=C(C=C(C(=C1)F)F)NC(=S)Cl AVAIQPJKRMLGGR-UHFFFAOYSA-N 0.000 description 1
- NOCPAZULKASWST-UHFFFAOYSA-N FC1=C(C(=CC=C1)I)NC(=O)Cl.FC1=C(C=C(C=C1)I)NC(=O)Cl Chemical compound FC1=C(C(=CC=C1)I)NC(=O)Cl.FC1=C(C=C(C=C1)I)NC(=O)Cl NOCPAZULKASWST-UHFFFAOYSA-N 0.000 description 1
- MVMVJMULQKJUEC-UHFFFAOYSA-N FC1=C(C(=CC=C1F)F)S(=O)(=O)Cl.FC1=C(C=C(C=C1F)F)S(=O)(=O)Cl Chemical compound FC1=C(C(=CC=C1F)F)S(=O)(=O)Cl.FC1=C(C=C(C=C1F)F)S(=O)(=O)Cl MVMVJMULQKJUEC-UHFFFAOYSA-N 0.000 description 1
- XHYWOFRKTNHFPK-UHFFFAOYSA-N FC1=C(C=CC=C1C(F)(F)F)S(=O)(=O)Cl.FC1=C(C(=CC=C1)I)S(=O)(=O)Cl Chemical compound FC1=C(C=CC=C1C(F)(F)F)S(=O)(=O)Cl.FC1=C(C(=CC=C1)I)S(=O)(=O)Cl XHYWOFRKTNHFPK-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical group F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- GWEPGPGZPCOZMT-UHFFFAOYSA-N N-(2,3,4,5,6-pentafluorophenyl)carbamothioyl chloride Chemical compound FC1=C(C(=C(C(=C1F)F)F)F)NC(=S)Cl GWEPGPGZPCOZMT-UHFFFAOYSA-N 0.000 description 1
- MKMHBSHHCUYJQG-UHFFFAOYSA-N N-(2,3,4,5,6-pentafluorophenyl)carbamoyl chloride Chemical compound FC1=C(C(=C(C(=C1F)F)F)F)NC(=O)Cl MKMHBSHHCUYJQG-UHFFFAOYSA-N 0.000 description 1
- NIAPERDSSQYPPU-UHFFFAOYSA-N N-(2,3,4,5-tetrafluoro-6-nitrophenyl)carbamothioyl chloride Chemical compound FC1=C(C(=C(C(=C1F)F)F)[N+](=O)[O-])NC(=S)Cl NIAPERDSSQYPPU-UHFFFAOYSA-N 0.000 description 1
- UMSAXNMCAYKEAQ-UHFFFAOYSA-N N-(2,3,4,5-tetrafluoro-6-nitrophenyl)carbamoyl chloride Chemical compound FC1=C(C(=C(C(=C1F)F)F)[N+](=O)[O-])NC(=O)Cl UMSAXNMCAYKEAQ-UHFFFAOYSA-N 0.000 description 1
- WWUSMVKZMXHOJY-UHFFFAOYSA-N N-(2,3,4,5-tetrafluorophenyl)carbamothioyl chloride Chemical compound FC1=C(C=C(C(=C1F)F)F)NC(=S)Cl WWUSMVKZMXHOJY-UHFFFAOYSA-N 0.000 description 1
- GMBIFEYKWSXGNM-UHFFFAOYSA-N N-(2,3,4,5-tetrafluorophenyl)carbamoyl chloride Chemical compound FC1=C(C=C(C(=C1F)F)F)NC(=O)Cl GMBIFEYKWSXGNM-UHFFFAOYSA-N 0.000 description 1
- LCXOCPLHZVUBHU-UHFFFAOYSA-N N-(2,3,4-trifluorophenyl)carbamothioyl chloride Chemical compound FC1=C(C=CC(=C1F)F)NC(=S)Cl LCXOCPLHZVUBHU-UHFFFAOYSA-N 0.000 description 1
- BTTIVMYGWWTQCP-UHFFFAOYSA-N N-(2,3,4-trifluorophenyl)carbamoyl chloride Chemical compound FC1=C(C=CC(=C1F)F)NC(=O)Cl BTTIVMYGWWTQCP-UHFFFAOYSA-N 0.000 description 1
- JQDAXNYWESUGOZ-UHFFFAOYSA-N N-(2,3,5,6-tetrafluoro-4-methylphenyl)carbamothioyl chloride Chemical compound FC1=C(C(=C(C(=C1F)C)F)F)NC(=S)Cl JQDAXNYWESUGOZ-UHFFFAOYSA-N 0.000 description 1
- ADTXXIZZXFJPCQ-UHFFFAOYSA-N N-(2,3,5,6-tetrafluoro-4-methylphenyl)carbamoyl chloride Chemical compound FC1=C(C(=C(C(=C1F)C)F)F)NC(=O)Cl ADTXXIZZXFJPCQ-UHFFFAOYSA-N 0.000 description 1
- XAJOURPWOYLXSI-UHFFFAOYSA-N N-(2,3,5,6-tetrafluorophenyl)carbamothioyl chloride Chemical compound FC1=C(C(=C(C=C1F)F)F)NC(=S)Cl XAJOURPWOYLXSI-UHFFFAOYSA-N 0.000 description 1
- KJPZDNWJEQOHDG-UHFFFAOYSA-N N-(2,3,5,6-tetrafluorophenyl)carbamoyl chloride Chemical compound FC1=C(C(=C(C=C1F)F)F)NC(=O)Cl KJPZDNWJEQOHDG-UHFFFAOYSA-N 0.000 description 1
- QGNFNLJRTUKMKA-UHFFFAOYSA-N N-(2,3,5-trifluorophenyl)carbamothioyl chloride Chemical compound FC1=C(C=C(C=C1F)F)NC(=S)Cl QGNFNLJRTUKMKA-UHFFFAOYSA-N 0.000 description 1
- YCJKGJGIYQGCLZ-UHFFFAOYSA-N N-(2,3,5-trifluorophenyl)carbamoyl chloride Chemical compound FC1=C(C=C(C=C1F)F)NC(=O)Cl YCJKGJGIYQGCLZ-UHFFFAOYSA-N 0.000 description 1
- CWLJQXYKWJGCIJ-UHFFFAOYSA-N N-(2,3,6-trifluorophenyl)carbamothioyl chloride Chemical compound FC1=C(C(=CC=C1F)F)NC(=S)Cl CWLJQXYKWJGCIJ-UHFFFAOYSA-N 0.000 description 1
- DPFOCCAZVBSEPP-UHFFFAOYSA-N N-(2,3,6-trifluorophenyl)carbamoyl chloride Chemical compound FC1=C(C(=CC=C1F)F)NC(=O)Cl DPFOCCAZVBSEPP-UHFFFAOYSA-N 0.000 description 1
- UBVYNRTUXCVXJY-UHFFFAOYSA-N N-(2,3-difluorophenyl)carbamothioyl chloride Chemical compound FC1=C(C=CC=C1F)NC(=S)Cl UBVYNRTUXCVXJY-UHFFFAOYSA-N 0.000 description 1
- DADZCZSJGKICHH-UHFFFAOYSA-N N-(2,4,5-trifluoro-3-methyl-6-nitrophenyl)carbamothioyl chloride Chemical compound FC1=C(C(=C(C(=C1C)F)F)[N+](=O)[O-])NC(=S)Cl DADZCZSJGKICHH-UHFFFAOYSA-N 0.000 description 1
- PHHUMWQNDMEGDY-UHFFFAOYSA-N N-(2,4,5-trifluoro-3-methyl-6-nitrophenyl)carbamoyl chloride Chemical compound FC1=C(C(=C(C(=C1C)F)F)[N+](=O)[O-])NC(=O)Cl PHHUMWQNDMEGDY-UHFFFAOYSA-N 0.000 description 1
- PCCFSZUQUQTACP-UHFFFAOYSA-N N-(2,4,5-trifluorophenyl)carbamoyl chloride Chemical compound ClC(=O)NC1=C(C=C(C(=C1)F)F)F PCCFSZUQUQTACP-UHFFFAOYSA-N 0.000 description 1
- MDBSAVQOTWFFTO-UHFFFAOYSA-N N-(2,4,6-trifluorophenyl)carbamoyl chloride Chemical compound FC1=CC(F)=C(NC(Cl)=O)C(F)=C1 MDBSAVQOTWFFTO-UHFFFAOYSA-N 0.000 description 1
- BZLUXYZIKYTVBP-UHFFFAOYSA-N N-(2,4-dichloro-5-fluoro-4-nitrocyclohexa-1,5-dien-1-yl)carbamothioyl chloride Chemical compound ClC1=C(C=C(C(C1)([N+](=O)[O-])Cl)F)NC(=S)Cl BZLUXYZIKYTVBP-UHFFFAOYSA-N 0.000 description 1
- JFBWGPJWNVFKHR-UHFFFAOYSA-N N-(2,4-difluorophenyl)carbamothioyl chloride Chemical compound FC1=C(C=CC(=C1)F)NC(=S)Cl JFBWGPJWNVFKHR-UHFFFAOYSA-N 0.000 description 1
- YWFFQTIUQORARU-UHFFFAOYSA-N N-(2,5-difluorophenyl)carbamothioyl chloride Chemical compound FC1=C(C=C(C=C1)F)NC(=S)Cl YWFFQTIUQORARU-UHFFFAOYSA-N 0.000 description 1
- UBHRZQGFKDERSU-UHFFFAOYSA-N N-(2,5-difluorophenyl)carbamoyl chloride Chemical compound FC1=C(C=C(C=C1)F)NC(=O)Cl UBHRZQGFKDERSU-UHFFFAOYSA-N 0.000 description 1
- OJWWXSLAIGWHLS-UHFFFAOYSA-N N-(2,6-difluorophenyl)carbamothioyl chloride Chemical compound FC1=C(C(=CC=C1)F)NC(=S)Cl OJWWXSLAIGWHLS-UHFFFAOYSA-N 0.000 description 1
- ZTUSGSJHNAHLLK-UHFFFAOYSA-N N-(2,6-difluorophenyl)carbamoyl chloride Chemical compound FC1=C(C(=CC=C1)F)NC(=O)Cl ZTUSGSJHNAHLLK-UHFFFAOYSA-N 0.000 description 1
- XSAHHTPHALSWKF-UHFFFAOYSA-N N-(2-bromo-3-fluorophenyl)carbamothioyl chloride Chemical compound BrC1=C(C=CC=C1F)NC(=S)Cl XSAHHTPHALSWKF-UHFFFAOYSA-N 0.000 description 1
- KZEWFOGVOWNDLE-UHFFFAOYSA-N N-(2-bromo-3-fluorophenyl)carbamoyl chloride Chemical compound BrC1=C(C=CC=C1F)NC(=O)Cl KZEWFOGVOWNDLE-UHFFFAOYSA-N 0.000 description 1
- IHYSPMIWTLJHDC-UHFFFAOYSA-N N-(2-bromo-4-fluorophenyl)carbamothioyl chloride Chemical compound BrC1=C(C=CC(=C1)F)NC(=S)Cl IHYSPMIWTLJHDC-UHFFFAOYSA-N 0.000 description 1
- RTTRYZDDYBHTGM-UHFFFAOYSA-N N-(2-bromo-4-fluorophenyl)carbamoyl chloride Chemical compound BrC1=C(C=CC(=C1)F)NC(=O)Cl RTTRYZDDYBHTGM-UHFFFAOYSA-N 0.000 description 1
- BQBFGBNHJYTAMK-UHFFFAOYSA-N N-(2-bromo-5-fluorophenyl)carbamothioyl chloride Chemical compound BrC1=C(C=C(C=C1)F)NC(=S)Cl BQBFGBNHJYTAMK-UHFFFAOYSA-N 0.000 description 1
- AMPBWRGSTYEZGI-UHFFFAOYSA-N N-(2-bromo-5-fluorophenyl)carbamoyl chloride Chemical compound BrC1=C(C=C(C=C1)F)NC(=O)Cl AMPBWRGSTYEZGI-UHFFFAOYSA-N 0.000 description 1
- ROMZGPJPEGWWDL-UHFFFAOYSA-N N-(2-bromo-6-fluorophenyl)carbamothioyl chloride Chemical compound BrC1=C(C(=CC=C1)F)NC(=S)Cl ROMZGPJPEGWWDL-UHFFFAOYSA-N 0.000 description 1
- SIEIAAFNOHWNQT-UHFFFAOYSA-N N-(2-bromo-6-fluorophenyl)carbamoyl chloride Chemical compound BrC1=C(C(=CC=C1)F)NC(=O)Cl SIEIAAFNOHWNQT-UHFFFAOYSA-N 0.000 description 1
- FTZRSHVNAMPQNG-UHFFFAOYSA-N N-(2-chloro-3-fluorophenyl)carbamothioyl chloride Chemical compound ClC1=C(C=CC=C1F)NC(=S)Cl FTZRSHVNAMPQNG-UHFFFAOYSA-N 0.000 description 1
- PQXQZPGGMOWYHH-UHFFFAOYSA-N N-(2-chloro-3-fluorophenyl)carbamoyl chloride Chemical compound ClC1=C(C=CC=C1F)NC(=O)Cl PQXQZPGGMOWYHH-UHFFFAOYSA-N 0.000 description 1
- MJVUBOHBBFTODL-UHFFFAOYSA-N N-(2-chloro-4-fluorophenyl)carbamothioyl chloride Chemical compound ClC1=C(C=CC(=C1)F)NC(=S)Cl MJVUBOHBBFTODL-UHFFFAOYSA-N 0.000 description 1
- IRGKIJUBHFBSNJ-UHFFFAOYSA-N N-(2-chloro-5-fluorophenyl)carbamothioyl chloride Chemical compound ClC1=C(C=C(C=C1)F)NC(=S)Cl IRGKIJUBHFBSNJ-UHFFFAOYSA-N 0.000 description 1
- UHQMNXNNMCJXFO-UHFFFAOYSA-N N-(2-chloro-5-fluorophenyl)carbamoyl chloride Chemical compound ClC1=C(C=C(C=C1)F)NC(=O)Cl UHQMNXNNMCJXFO-UHFFFAOYSA-N 0.000 description 1
- JEMAHUZRFJYFIU-UHFFFAOYSA-N N-(2-chloro-6-fluorophenyl)carbamothioyl chloride Chemical compound ClC1=C(C(=CC=C1)F)NC(=S)Cl JEMAHUZRFJYFIU-UHFFFAOYSA-N 0.000 description 1
- GUIBWRIHWQBTGC-UHFFFAOYSA-N N-(2-chloro-6-fluorophenyl)carbamoyl chloride Chemical compound ClC1=C(C(=CC=C1)F)NC(=O)Cl GUIBWRIHWQBTGC-UHFFFAOYSA-N 0.000 description 1
- JHVBPPLPNZFXAP-UHFFFAOYSA-N N-(2-fluoro-4-methylphenyl)carbamothioyl chloride Chemical compound FC1=C(C=CC(=C1)C)NC(=S)Cl JHVBPPLPNZFXAP-UHFFFAOYSA-N 0.000 description 1
- MJSJGTAYWYAFCQ-UHFFFAOYSA-N N-(2-fluoro-4-methylphenyl)carbamoyl chloride Chemical compound FC1=C(C=CC(=C1)C)NC(=O)Cl MJSJGTAYWYAFCQ-UHFFFAOYSA-N 0.000 description 1
- YIGDSWHETPLLAH-UHFFFAOYSA-N N-(2-fluoro-4-nitrophenyl)carbamothioyl chloride Chemical compound FC1=C(C=CC(=C1)[N+](=O)[O-])NC(=S)Cl YIGDSWHETPLLAH-UHFFFAOYSA-N 0.000 description 1
- DCUWPDHXESYQSQ-UHFFFAOYSA-N N-(2-fluoro-5-iodophenyl)carbamothioyl chloride Chemical compound FC1=C(C=C(C=C1)I)NC(=S)Cl DCUWPDHXESYQSQ-UHFFFAOYSA-N 0.000 description 1
- RCFUNVRRMONUBH-UHFFFAOYSA-N N-(2-fluoro-5-methylphenyl)carbamothioyl chloride Chemical compound FC1=C(C=C(C=C1)C)NC(=S)Cl RCFUNVRRMONUBH-UHFFFAOYSA-N 0.000 description 1
- XETYCFFJPQZKGH-UHFFFAOYSA-N N-(2-fluoro-5-nitrophenyl)carbamothioyl chloride Chemical compound FC1=C(C=C(C=C1)[N+](=O)[O-])NC(=S)Cl XETYCFFJPQZKGH-UHFFFAOYSA-N 0.000 description 1
- HENKGRQKBAIFCA-UHFFFAOYSA-N N-(2-fluoro-5-nitrophenyl)carbamoyl chloride Chemical compound FC1=C(C=C(C=C1)[N+](=O)[O-])NC(=O)Cl HENKGRQKBAIFCA-UHFFFAOYSA-N 0.000 description 1
- PCFOAWJXZYXNPF-UHFFFAOYSA-N N-(2-fluorophenyl)carbamothioyl chloride Chemical compound FC1=C(C=CC=C1)NC(=S)Cl PCFOAWJXZYXNPF-UHFFFAOYSA-N 0.000 description 1
- NFMRTLWXPPRJAD-UHFFFAOYSA-N N-(2-fluorophenyl)carbamoyl chloride Chemical compound FC1=CC=CC=C1NC(Cl)=O NFMRTLWXPPRJAD-UHFFFAOYSA-N 0.000 description 1
- CSDUWKPWHKDKQX-UHFFFAOYSA-N N-(3,4,5-trifluorophenyl)carbamothioyl chloride Chemical compound FC=1C=C(C=C(C=1F)F)NC(=S)Cl CSDUWKPWHKDKQX-UHFFFAOYSA-N 0.000 description 1
- LJNWOUWYKTUELR-UHFFFAOYSA-N N-(3,4,5-trifluorophenyl)carbamoyl chloride Chemical compound FC=1C=C(C=C(C=1F)F)NC(=O)Cl LJNWOUWYKTUELR-UHFFFAOYSA-N 0.000 description 1
- QYMCYAJEADFYKI-UHFFFAOYSA-N N-(3,4-difluorophenyl)carbamothioyl chloride Chemical compound FC=1C=C(C=CC=1F)NC(=S)Cl QYMCYAJEADFYKI-UHFFFAOYSA-N 0.000 description 1
- JVQTUGNADZDXEM-UHFFFAOYSA-N N-(3,4-difluorophenyl)carbamoyl chloride Chemical compound FC=1C=C(C=CC=1F)NC(=O)Cl JVQTUGNADZDXEM-UHFFFAOYSA-N 0.000 description 1
- DEVYBDHSFWOBDY-UHFFFAOYSA-N N-(3,5-difluorophenyl)carbamothioyl chloride Chemical compound FC=1C=C(C=C(C=1)F)NC(=S)Cl DEVYBDHSFWOBDY-UHFFFAOYSA-N 0.000 description 1
- FXRRIUQRXGZZJZ-UHFFFAOYSA-N N-(3-bromo-2-fluorophenyl)carbamothioyl chloride Chemical compound BrC=1C(=C(C=CC=1)NC(=S)Cl)F FXRRIUQRXGZZJZ-UHFFFAOYSA-N 0.000 description 1
- DRUTVFKFBZECTD-UHFFFAOYSA-N N-(3-bromo-2-fluorophenyl)carbamoyl chloride Chemical compound BrC=1C(=C(C=CC=1)NC(=O)Cl)F DRUTVFKFBZECTD-UHFFFAOYSA-N 0.000 description 1
- ZIUXIKUXZPCQBO-UHFFFAOYSA-N N-(3-bromo-4-fluorophenyl)carbamothioyl chloride Chemical compound BrC=1C=C(C=CC=1F)NC(=S)Cl ZIUXIKUXZPCQBO-UHFFFAOYSA-N 0.000 description 1
- KYCXELFKVXJTQZ-UHFFFAOYSA-N N-(3-bromo-4-fluorophenyl)carbamoyl chloride Chemical compound BrC=1C=C(C=CC=1F)NC(=O)Cl KYCXELFKVXJTQZ-UHFFFAOYSA-N 0.000 description 1
- FKIPRYLSFAMXDM-UHFFFAOYSA-N N-(3-bromo-5-fluorophenyl)carbamothioyl chloride Chemical compound BrC=1C=C(C=C(C=1)F)NC(=S)Cl FKIPRYLSFAMXDM-UHFFFAOYSA-N 0.000 description 1
- OJTDKAMCPJGQOU-UHFFFAOYSA-N N-(3-bromo-5-fluorophenyl)carbamoyl chloride Chemical compound BrC=1C=C(C=C(C=1)F)NC(=O)Cl OJTDKAMCPJGQOU-UHFFFAOYSA-N 0.000 description 1
- DKABLCDHHUHLJN-UHFFFAOYSA-N N-(3-chloro-2-fluorophenyl)carbamothioyl chloride Chemical compound ClC=1C(=C(C=CC=1)NC(=S)Cl)F DKABLCDHHUHLJN-UHFFFAOYSA-N 0.000 description 1
- HLHFVPJRXYWHCY-UHFFFAOYSA-N N-(3-chloro-2-fluorophenyl)carbamoyl chloride Chemical compound ClC=1C(=C(C=CC=1)NC(=O)Cl)F HLHFVPJRXYWHCY-UHFFFAOYSA-N 0.000 description 1
- QAWLXCOCHBPSQX-UHFFFAOYSA-N N-(3-chloro-4-fluorophenyl)carbamothioyl chloride Chemical compound ClC=1C=C(C=CC=1F)NC(=S)Cl QAWLXCOCHBPSQX-UHFFFAOYSA-N 0.000 description 1
- RXONTVPZTFKPOM-UHFFFAOYSA-N N-(3-chloro-4-fluorophenyl)carbamoyl chloride Chemical compound ClC=1C=C(C=CC=1F)NC(=O)Cl RXONTVPZTFKPOM-UHFFFAOYSA-N 0.000 description 1
- GBSWWIGNPRMSQG-UHFFFAOYSA-N N-(3-chloro-5-fluorophenyl)carbamothioyl chloride Chemical compound ClC=1C=C(C=C(C=1)F)NC(=S)Cl GBSWWIGNPRMSQG-UHFFFAOYSA-N 0.000 description 1
- NUIPRVNLSACQOB-UHFFFAOYSA-N N-(3-chloro-5-fluorophenyl)carbamoyl chloride Chemical compound ClC=1C=C(C=C(C=1)F)NC(=O)Cl NUIPRVNLSACQOB-UHFFFAOYSA-N 0.000 description 1
- ONVCORDOLAUDQW-UHFFFAOYSA-N N-(3-cyano-5-fluorophenyl)carbamothioyl chloride Chemical compound C(#N)C=1C=C(C=C(C=1)F)NC(=S)Cl ONVCORDOLAUDQW-UHFFFAOYSA-N 0.000 description 1
- MYMBUKYQCIUIHD-UHFFFAOYSA-N N-(3-cyano-5-fluorophenyl)carbamoyl chloride Chemical compound C(#N)C=1C=C(C=C(C=1)F)NC(=O)Cl MYMBUKYQCIUIHD-UHFFFAOYSA-N 0.000 description 1
- UQTPZEVANWBVQZ-UHFFFAOYSA-N N-(3-fluoro-2-nitrophenyl)carbamothioyl chloride Chemical compound FC=1C(=C(C=CC=1)NC(=S)Cl)[N+](=O)[O-] UQTPZEVANWBVQZ-UHFFFAOYSA-N 0.000 description 1
- IYVFRAWOXCELRG-UHFFFAOYSA-N N-(3-fluoro-2-nitrophenyl)carbamoyl chloride Chemical compound FC=1C(=C(C=CC=1)NC(=O)Cl)[N+](=O)[O-] IYVFRAWOXCELRG-UHFFFAOYSA-N 0.000 description 1
- PAXNFTYNOLFNIH-UHFFFAOYSA-N N-(3-fluoro-4-methylphenyl)carbamothioyl chloride Chemical compound FC=1C=C(C=CC=1C)NC(=S)Cl PAXNFTYNOLFNIH-UHFFFAOYSA-N 0.000 description 1
- NARRUXJKPARFAG-UHFFFAOYSA-N N-(3-fluoro-4-methylphenyl)carbamoyl chloride Chemical compound FC=1C=C(C=CC=1C)NC(=O)Cl NARRUXJKPARFAG-UHFFFAOYSA-N 0.000 description 1
- WTFDVCPARYBXIC-UHFFFAOYSA-N N-(3-fluoro-4-nitrophenyl)carbamothioyl chloride Chemical compound FC=1C=C(C=CC=1[N+](=O)[O-])NC(=S)Cl WTFDVCPARYBXIC-UHFFFAOYSA-N 0.000 description 1
- WRXNVAXTQIWTCO-UHFFFAOYSA-N N-(3-fluoro-4-nitrophenyl)carbamoyl chloride Chemical compound FC=1C=C(C=CC=1[N+](=O)[O-])NC(=O)Cl WRXNVAXTQIWTCO-UHFFFAOYSA-N 0.000 description 1
- FCMJHTVNYBVSRB-UHFFFAOYSA-N N-(3-fluorophenyl)carbamothioyl chloride Chemical compound FC=1C=C(C=CC=1)NC(=S)Cl FCMJHTVNYBVSRB-UHFFFAOYSA-N 0.000 description 1
- HHDUGEPVVMCBTQ-UHFFFAOYSA-N N-(4-bromo-2-fluorophenyl)carbamothioyl chloride Chemical compound BrC1=CC(=C(C=C1)NC(=S)Cl)F HHDUGEPVVMCBTQ-UHFFFAOYSA-N 0.000 description 1
- JSHNQVQVMYLPSJ-UHFFFAOYSA-N N-(4-bromo-2-fluorophenyl)carbamoyl chloride Chemical compound BrC1=CC(=C(C=C1)NC(=O)Cl)F JSHNQVQVMYLPSJ-UHFFFAOYSA-N 0.000 description 1
- PZTJYONVJFGHRQ-UHFFFAOYSA-N N-(4-chloro-2,4-difluorocyclohexa-1,5-dien-1-yl)carbamothioyl chloride Chemical compound ClC1(CC(=C(C=C1)NC(=S)Cl)F)F PZTJYONVJFGHRQ-UHFFFAOYSA-N 0.000 description 1
- YWLQTJAITBQFMX-UHFFFAOYSA-N N-(4-chloro-2,4-difluorocyclohexa-1,5-dien-1-yl)carbamoyl chloride Chemical compound ClC1(CC(=C(C=C1)NC(=O)Cl)F)F YWLQTJAITBQFMX-UHFFFAOYSA-N 0.000 description 1
- ILGJBWKATMJHOU-UHFFFAOYSA-N N-(4-cyano-2-fluorophenyl)carbamothioyl chloride Chemical compound C(#N)C1=CC(=C(C=C1)NC(=S)Cl)F ILGJBWKATMJHOU-UHFFFAOYSA-N 0.000 description 1
- YCRWVICPVQLFES-UHFFFAOYSA-N N-(4-cyano-2-fluorophenyl)carbamoyl chloride Chemical compound C(#N)C1=CC(=C(C=C1)NC(=O)Cl)F YCRWVICPVQLFES-UHFFFAOYSA-N 0.000 description 1
- FUUKLBRDLWSJOG-UHFFFAOYSA-N N-(4-fluoro-2-methylphenyl)carbamothioyl chloride Chemical compound FC1=CC(=C(C=C1)NC(=S)Cl)C FUUKLBRDLWSJOG-UHFFFAOYSA-N 0.000 description 1
- QNKDNLPUWVQNSZ-UHFFFAOYSA-N N-(4-fluoro-2-nitrophenyl)carbamothioyl chloride Chemical compound FC1=CC(=C(C=C1)NC(=S)Cl)[N+](=O)[O-] QNKDNLPUWVQNSZ-UHFFFAOYSA-N 0.000 description 1
- MVXNWNZZVGMDHL-UHFFFAOYSA-N N-(4-fluoro-3-methylphenyl)carbamothioyl chloride Chemical compound FC1=C(C=C(C=C1)NC(=S)Cl)C MVXNWNZZVGMDHL-UHFFFAOYSA-N 0.000 description 1
- LIGGAWRJFFBSIB-UHFFFAOYSA-N N-(4-fluoro-3-methylphenyl)carbamoyl chloride Chemical compound Cc1cc(NC(Cl)=O)ccc1F LIGGAWRJFFBSIB-UHFFFAOYSA-N 0.000 description 1
- ZVJNGZNFGYNZCM-UHFFFAOYSA-N N-(4-fluoro-3-nitrophenyl)carbamothioyl chloride Chemical compound FC1=C(C=C(C=C1)NC(=S)Cl)[N+](=O)[O-] ZVJNGZNFGYNZCM-UHFFFAOYSA-N 0.000 description 1
- SGXLKWMBISFBPP-UHFFFAOYSA-N N-(4-fluoro-3-nitrophenyl)carbamoyl chloride Chemical compound FC1=C(C=C(C=C1)NC(=O)Cl)[N+](=O)[O-] SGXLKWMBISFBPP-UHFFFAOYSA-N 0.000 description 1
- OTSMDXMNNCNRAM-UHFFFAOYSA-N N-(4-fluorophenyl)carbamothioyl chloride Chemical compound FC1=CC=C(C=C1)NC(=S)Cl OTSMDXMNNCNRAM-UHFFFAOYSA-N 0.000 description 1
- NNXGWWXXZOLMQW-UHFFFAOYSA-N N-(5-bromo-2-fluorophenyl)carbamothioyl chloride Chemical compound BrC=1C=CC(=C(C=1)NC(=S)Cl)F NNXGWWXXZOLMQW-UHFFFAOYSA-N 0.000 description 1
- QOAYIYMEDFQERY-UHFFFAOYSA-N N-(5-bromo-2-fluorophenyl)carbamoyl chloride Chemical compound BrC=1C=CC(=C(C=1)NC(=O)Cl)F QOAYIYMEDFQERY-UHFFFAOYSA-N 0.000 description 1
- GHLZCNMTAGCVJP-UHFFFAOYSA-N N-(5-chloro-2-fluorophenyl)carbamothioyl chloride Chemical compound ClC=1C=CC(=C(C=1)NC(=S)Cl)F GHLZCNMTAGCVJP-UHFFFAOYSA-N 0.000 description 1
- HAPSBZBLMHIXDK-UHFFFAOYSA-N N-(5-chloro-2-fluorophenyl)carbamoyl chloride Chemical compound ClC=1C=CC(=C(C=1)NC(=O)Cl)F HAPSBZBLMHIXDK-UHFFFAOYSA-N 0.000 description 1
- SRXVPJHISBFFGM-UHFFFAOYSA-N N-(5-fluoro-2-methylphenyl)carbamothioyl chloride Chemical compound FC=1C=C(C(=CC=1)C)NC(=S)Cl SRXVPJHISBFFGM-UHFFFAOYSA-N 0.000 description 1
- IGJCTEFWHQYFLO-UHFFFAOYSA-N N-(5-fluoro-2-methylphenyl)carbamoyl chloride Chemical compound FC=1C=C(C(=CC=1)C)NC(=O)Cl IGJCTEFWHQYFLO-UHFFFAOYSA-N 0.000 description 1
- WGPPZZHGOVOBCK-UHFFFAOYSA-N N-(5-fluoro-2-nitrophenyl)carbamothioyl chloride Chemical compound FC=1C=C(C(=CC=1)[N+](=O)[O-])NC(=S)Cl WGPPZZHGOVOBCK-UHFFFAOYSA-N 0.000 description 1
- RTOQYKHDINKPQJ-UHFFFAOYSA-N N-(5-fluoro-2-nitrophenyl)carbamoyl chloride Chemical compound FC=1C=C(C(=CC=1)[N+](=O)[O-])NC(=O)Cl RTOQYKHDINKPQJ-UHFFFAOYSA-N 0.000 description 1
- FNMPYTPLCZIYFM-UHFFFAOYSA-N N-[2,3,5,6-tetrafluoro-4-(1,2,2-trifluoroethenyl)phenyl]carbamothioyl chloride Chemical compound FC1=C(C(=C(C(=C1F)C(=C(F)F)F)F)F)NC(=S)Cl FNMPYTPLCZIYFM-UHFFFAOYSA-N 0.000 description 1
- PXLJEJSAZUCACI-UHFFFAOYSA-N N-[2,3,5,6-tetrafluoro-4-(1,2,2-trifluoroethenyl)phenyl]carbamoyl chloride Chemical compound FC1=C(C(=C(C(=C1F)C(=C(F)F)F)F)F)NC(=O)Cl PXLJEJSAZUCACI-UHFFFAOYSA-N 0.000 description 1
- LJPNPMJLYIGPPZ-UHFFFAOYSA-N N-[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl]carbamothioyl chloride Chemical compound FC1=C(C(=C(C(=C1F)C(F)(F)F)F)F)NC(=S)Cl LJPNPMJLYIGPPZ-UHFFFAOYSA-N 0.000 description 1
- RPUXYWGEYAWTRF-UHFFFAOYSA-N N-[2,4,6-tris(trifluoromethyl)phenyl]carbamothioyl chloride Chemical compound FC(C1=C(C(=CC(=C1)C(F)(F)F)C(F)(F)F)NC(=S)Cl)(F)F RPUXYWGEYAWTRF-UHFFFAOYSA-N 0.000 description 1
- VVCKILHJHOJWOD-UHFFFAOYSA-N N-[2,4,6-tris(trifluoromethyl)phenyl]carbamoyl chloride Chemical compound FC(C1=C(C(=CC(=C1)C(F)(F)F)C(F)(F)F)NC(=O)Cl)(F)F VVCKILHJHOJWOD-UHFFFAOYSA-N 0.000 description 1
- LJMSBHGHPUBWKW-UHFFFAOYSA-N N-[2-(trifluoromethyl)phenyl]carbamothioyl chloride Chemical compound FC(C1=CC=CC=C1NC(=S)Cl)(F)F LJMSBHGHPUBWKW-UHFFFAOYSA-N 0.000 description 1
- HZSCTLTXMSLXMF-UHFFFAOYSA-N N-[2-fluoro-3-(trifluoromethyl)phenyl]carbamothioyl chloride Chemical compound FC1=C(C=CC=C1C(F)(F)F)NC(=S)Cl HZSCTLTXMSLXMF-UHFFFAOYSA-N 0.000 description 1
- YUYCMMAJZBVGME-UHFFFAOYSA-N N-[2-fluoro-3-(trifluoromethyl)phenyl]carbamoyl chloride Chemical compound FC1=C(C=CC=C1C(F)(F)F)NC(=O)Cl YUYCMMAJZBVGME-UHFFFAOYSA-N 0.000 description 1
- ZLHRLXYNBBLVHA-UHFFFAOYSA-N N-[2-fluoro-5-(trifluoromethyl)phenyl]carbamothioyl chloride Chemical compound FC1=C(C=C(C=C1)C(F)(F)F)NC(=S)Cl ZLHRLXYNBBLVHA-UHFFFAOYSA-N 0.000 description 1
- LEENZNYCLMOSBT-UHFFFAOYSA-N N-[2-fluoro-6-(trifluoromethyl)phenyl]carbamothioyl chloride Chemical compound FC1=C(C(=CC=C1)C(F)(F)F)NC(=S)Cl LEENZNYCLMOSBT-UHFFFAOYSA-N 0.000 description 1
- DFRPYPNGLNWNBY-UHFFFAOYSA-N N-[2-fluoro-6-(trifluoromethyl)phenyl]carbamoyl chloride Chemical compound FC1=C(C(=CC=C1)C(F)(F)F)NC(=O)Cl DFRPYPNGLNWNBY-UHFFFAOYSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- JUOULMABLSTJSO-UHFFFAOYSA-N N-[3,5-bis(trifluoromethyl)phenyl]carbamothioyl chloride Chemical compound FC(C=1C=C(C=C(C=1)C(F)(F)F)NC(=S)Cl)(F)F JUOULMABLSTJSO-UHFFFAOYSA-N 0.000 description 1
- FEQKPISDDSEWEM-UHFFFAOYSA-N N-[3-(trifluoromethyl)phenyl]carbamothioyl chloride Chemical compound FC(C=1C=C(C=CC=1)NC(=S)Cl)(F)F FEQKPISDDSEWEM-UHFFFAOYSA-N 0.000 description 1
- XJVZRUARIYAWEG-UHFFFAOYSA-N N-[3-fluoro-4-(trifluoromethyl)phenyl]carbamothioyl chloride Chemical compound FC=1C=C(C=CC=1C(F)(F)F)NC(=S)Cl XJVZRUARIYAWEG-UHFFFAOYSA-N 0.000 description 1
- LSSHQWKWWSOVRE-UHFFFAOYSA-N N-[3-fluoro-4-(trifluoromethyl)phenyl]carbamoyl chloride Chemical compound FC=1C=C(C=CC=1C(F)(F)F)NC(=O)Cl LSSHQWKWWSOVRE-UHFFFAOYSA-N 0.000 description 1
- SQTGBDQZEITXTO-UHFFFAOYSA-N N-[3-fluoro-5-(trifluoromethyl)phenyl]carbamothioyl chloride Chemical compound FC=1C=C(C=C(C=1)C(F)(F)F)NC(=S)Cl SQTGBDQZEITXTO-UHFFFAOYSA-N 0.000 description 1
- OCUZDAXWDKNGDF-UHFFFAOYSA-N N-[3-fluoro-5-(trifluoromethyl)phenyl]carbamoyl chloride Chemical compound FC=1C=C(C=C(C=1)C(F)(F)F)NC(=O)Cl OCUZDAXWDKNGDF-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- UYNVJIZOJRRBJV-UHFFFAOYSA-N N-[4-(1,1,2,2,2-pentafluoroethyl)phenyl]carbamothioyl chloride Chemical compound FC(C(F)(F)F)(C1=CC=C(C=C1)NC(=S)Cl)F UYNVJIZOJRRBJV-UHFFFAOYSA-N 0.000 description 1
- UMZQVZIXZOILHZ-UHFFFAOYSA-N N-[4-(1,1,2,2,2-pentafluoroethyl)phenyl]carbamoyl chloride Chemical compound FC(C(F)(F)F)(C1=CC=C(C=C1)NC(=O)Cl)F UMZQVZIXZOILHZ-UHFFFAOYSA-N 0.000 description 1
- XMZHUYSWXZNFCH-UHFFFAOYSA-N N-[4-(trifluoromethyl)phenyl]carbamothioyl chloride Chemical compound FC(C1=CC=C(C=C1)NC(=S)Cl)(F)F XMZHUYSWXZNFCH-UHFFFAOYSA-N 0.000 description 1
- UNJHPOBEHXONPV-UHFFFAOYSA-N N-[4-ethoxy-3-(trifluoromethyl)phenyl]carbamothioyl chloride Chemical compound FC(C=1C=C(C=CC=1OCC)NC(=S)Cl)(F)F UNJHPOBEHXONPV-UHFFFAOYSA-N 0.000 description 1
- HTQXWZMTVFFJHY-UHFFFAOYSA-N N-[4-ethoxy-3-(trifluoromethyl)phenyl]carbamoyl chloride Chemical compound FC(C=1C=C(C=CC=1OCC)NC(=O)Cl)(F)F HTQXWZMTVFFJHY-UHFFFAOYSA-N 0.000 description 1
- ONGPNASLWDBZPR-UHFFFAOYSA-N N-[4-fluoro-2-(trifluoromethyl)phenyl]carbamothioyl chloride Chemical compound FC1=CC(=C(C=C1)NC(=S)Cl)C(F)(F)F ONGPNASLWDBZPR-UHFFFAOYSA-N 0.000 description 1
- RBSRLPWPAFUIIH-UHFFFAOYSA-N N-[4-fluoro-2-(trifluoromethyl)phenyl]carbamoyl chloride Chemical compound FC1=CC(=C(C=C1)NC(=O)Cl)C(F)(F)F RBSRLPWPAFUIIH-UHFFFAOYSA-N 0.000 description 1
- ROLJEXAPZXQUPD-UHFFFAOYSA-N N-[4-fluoro-3-(trifluoromethyl)phenyl]carbamothioyl chloride Chemical compound FC1=C(C=C(C=C1)NC(=S)Cl)C(F)(F)F ROLJEXAPZXQUPD-UHFFFAOYSA-N 0.000 description 1
- SDSRLUGDNHHTFD-UHFFFAOYSA-N N-[4-fluoro-3-(trifluoromethyl)phenyl]carbamoyl chloride Chemical compound FC1=C(C=C(C=C1)NC(=O)Cl)C(F)(F)F SDSRLUGDNHHTFD-UHFFFAOYSA-N 0.000 description 1
- YORXFHHXEXEXJJ-UHFFFAOYSA-N N-[5-fluoro-2-(trifluoromethyl)phenyl]carbamothioyl chloride Chemical compound FC=1C=C(C(=CC=1)C(F)(F)F)NC(=S)Cl YORXFHHXEXEXJJ-UHFFFAOYSA-N 0.000 description 1
- QJAZXJVPBGZACA-UHFFFAOYSA-N N-[5-fluoro-2-(trifluoromethyl)phenyl]carbamoyl chloride Chemical compound FC=1C=C(C(=CC=1)C(F)(F)F)NC(=O)Cl QJAZXJVPBGZACA-UHFFFAOYSA-N 0.000 description 1
- LBHLUAPJUJTMJT-UHFFFAOYSA-N NC1=CC=C(C=C1)C1(C2=CC(=CC=C2C=2C=CC(=CC1=2)C1=CC=C(C=C1)NC1=CC=CC=C1)C1=CC=C(C=C1)NC1=CC=CC=C1)C1=CC=C(C=C1)N Chemical compound NC1=CC=C(C=C1)C1(C2=CC(=CC=C2C=2C=CC(=CC1=2)C1=CC=C(C=C1)NC1=CC=CC=C1)C1=CC=C(C=C1)NC1=CC=CC=C1)C1=CC=C(C=C1)N LBHLUAPJUJTMJT-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910018287 SbF 5 Inorganic materials 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UXKZFJDNFBNQHE-RITPCOANSA-N [(1s,4r)-4-aminocyclopent-2-en-1-yl]methanol Chemical compound N[C@@H]1C[C@H](CO)C=C1 UXKZFJDNFBNQHE-RITPCOANSA-N 0.000 description 1
- TWWQCBRELPOMER-UHFFFAOYSA-N [4-(n-phenylanilino)phenyl]boronic acid Chemical compound C1=CC(B(O)O)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 TWWQCBRELPOMER-UHFFFAOYSA-N 0.000 description 1
- DSVGQVZAZSZEEX-UHFFFAOYSA-N [C].[Pt] Chemical compound [C].[Pt] DSVGQVZAZSZEEX-UHFFFAOYSA-N 0.000 description 1
- OWWNJDFZTCNNNX-UHFFFAOYSA-N [Na].[Na].OS(=O)(=O)C1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 Chemical compound [Na].[Na].OS(=O)(=O)C1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 OWWNJDFZTCNNNX-UHFFFAOYSA-N 0.000 description 1
- CITSQVLCCYLECV-UHFFFAOYSA-N [O-][N+](c1ccc(C2(c3cc(-c(cc4)ccc4-[n]4c5ccccc5c5c4cccc5)ccc3-c(cc3)c2cc3-c(cc2)ccc2-[n]2c3ccccc3c3c2cccc3)c(cc2)ccc2[N+]([O-])=O)cc1)=O Chemical compound [O-][N+](c1ccc(C2(c3cc(-c(cc4)ccc4-[n]4c5ccccc5c5c4cccc5)ccc3-c(cc3)c2cc3-c(cc2)ccc2-[n]2c3ccccc3c3c2cccc3)c(cc2)ccc2[N+]([O-])=O)cc1)=O CITSQVLCCYLECV-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical group 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000005577 anthracene group Chemical group 0.000 description 1
- VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 description 1
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 1
- YBGKQGSCGDNZIB-UHFFFAOYSA-N arsenic pentafluoride Chemical compound F[As](F)(F)(F)F YBGKQGSCGDNZIB-UHFFFAOYSA-N 0.000 description 1
- MNUYNGXMQRGJSJ-UHFFFAOYSA-N benzenecarbothioyl chloride Chemical compound ClC(=S)C1=CC=CC=C1 MNUYNGXMQRGJSJ-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- AQIHMSVIAGNIDM-UHFFFAOYSA-N benzoyl bromide Chemical compound BrC(=O)C1=CC=CC=C1 AQIHMSVIAGNIDM-UHFFFAOYSA-N 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 150000001602 bicycloalkyls Chemical group 0.000 description 1
- 150000003519 bicyclobutyls Chemical group 0.000 description 1
- 150000005350 bicyclononyls Chemical group 0.000 description 1
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical group C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 0.000 description 1
- JMVIPXWCEHBYAH-UHFFFAOYSA-N cyclohexanone;ethyl acetate Chemical compound CCOC(C)=O.O=C1CCCCC1 JMVIPXWCEHBYAH-UHFFFAOYSA-N 0.000 description 1
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical group C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 description 1
- 125000006547 cyclononyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- NLUNLVTVUDIHFE-UHFFFAOYSA-N cyclooctylcyclooctane Chemical group C1CCCCCCC1C1CCCCCCC1 NLUNLVTVUDIHFE-UHFFFAOYSA-N 0.000 description 1
- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- MAWOHFOSAIXURX-UHFFFAOYSA-N cyclopentylcyclopentane Chemical group C1CCCC1C1CCCC1 MAWOHFOSAIXURX-UHFFFAOYSA-N 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- QYUDDCLXBAJUNA-UHFFFAOYSA-L disodium;2-aminobenzene-1,4-disulfonate Chemical compound [Na+].[Na+].NC1=CC(S([O-])(=O)=O)=CC=C1S([O-])(=O)=O QYUDDCLXBAJUNA-UHFFFAOYSA-L 0.000 description 1
- ACBJGAPIXKDCRP-UHFFFAOYSA-L disodium;2-aminonaphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=CC=CC2=C(S([O-])(=O)=O)C(N)=CC=C21 ACBJGAPIXKDCRP-UHFFFAOYSA-L 0.000 description 1
- UZUODNWWWUQRIR-UHFFFAOYSA-L disodium;3-aminonaphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].C1=CC=C(S([O-])(=O)=O)C2=CC(N)=CC(S([O-])(=O)=O)=C21 UZUODNWWWUQRIR-UHFFFAOYSA-L 0.000 description 1
- YCBINYVMSDDQKZ-UHFFFAOYSA-L disodium;3-aminonaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(N)=CC2=C1 YCBINYVMSDDQKZ-UHFFFAOYSA-L 0.000 description 1
- OIZLWWGSWBNNAM-UHFFFAOYSA-L disodium;4-aminobenzene-1,3-disulfonate Chemical compound [Na+].[Na+].NC1=CC=C(S([O-])(=O)=O)C=C1S([O-])(=O)=O OIZLWWGSWBNNAM-UHFFFAOYSA-L 0.000 description 1
- QJEOKSBCNIUFDS-UHFFFAOYSA-L disodium;4-aminonaphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].C1=CC(S([O-])(=O)=O)=C2C(N)=CC=C(S([O-])(=O)=O)C2=C1 QJEOKSBCNIUFDS-UHFFFAOYSA-L 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000010304 firing Methods 0.000 description 1
- 150000004673 fluoride salts Chemical class 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 125000005816 fluoropropyl group Chemical group [H]C([H])(F)C([H])([H])C([H])([H])* 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000006343 heptafluoro propyl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229940051250 hexylene glycol Drugs 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- RPNNPZHFJPXFQS-UHFFFAOYSA-N methane;rhodium Chemical compound C.[Rh] RPNNPZHFJPXFQS-UHFFFAOYSA-N 0.000 description 1
- NCPHGZWGGANCAY-UHFFFAOYSA-N methane;ruthenium Chemical compound C.[Ru] NCPHGZWGGANCAY-UHFFFAOYSA-N 0.000 description 1
- 125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- HQWDBSLSKPZDEC-UHFFFAOYSA-N n-(2,3-difluorophenyl)carbamoyl chloride Chemical compound FC1=CC=CC(NC(Cl)=O)=C1F HQWDBSLSKPZDEC-UHFFFAOYSA-N 0.000 description 1
- CZUFGLOLGIJQLE-UHFFFAOYSA-N n-(2,4-difluorophenyl)carbamoyl chloride Chemical compound FC1=CC=C(NC(Cl)=O)C(F)=C1 CZUFGLOLGIJQLE-UHFFFAOYSA-N 0.000 description 1
- KKCIGDPNWLDUPR-UHFFFAOYSA-N n-(2-chloro-4-fluorophenyl)carbamoyl chloride Chemical compound FC1=CC=C(NC(Cl)=O)C(Cl)=C1 KKCIGDPNWLDUPR-UHFFFAOYSA-N 0.000 description 1
- RHANNOCKAHEHIP-UHFFFAOYSA-N n-(2-fluoro-4-nitrophenyl)carbamoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(NC(Cl)=O)C(F)=C1 RHANNOCKAHEHIP-UHFFFAOYSA-N 0.000 description 1
- LFSIDOWAZWRXRI-UHFFFAOYSA-N n-(2-fluoro-5-methylphenyl)carbamoyl chloride Chemical compound CC1=CC=C(F)C(NC(Cl)=O)=C1 LFSIDOWAZWRXRI-UHFFFAOYSA-N 0.000 description 1
- PRSWHEHEVBJHMB-UHFFFAOYSA-N n-(3,5-difluorophenyl)carbamoyl chloride Chemical compound FC1=CC(F)=CC(NC(Cl)=O)=C1 PRSWHEHEVBJHMB-UHFFFAOYSA-N 0.000 description 1
- XJPDWXIOEPLRQE-UHFFFAOYSA-N n-(3-fluorophenyl)carbamoyl chloride Chemical compound FC1=CC=CC(NC(Cl)=O)=C1 XJPDWXIOEPLRQE-UHFFFAOYSA-N 0.000 description 1
- RUGHVYVBGOKCSZ-UHFFFAOYSA-N n-(4-chloro-2-fluorophenyl)carbamoyl chloride Chemical compound FC1=CC(Cl)=CC=C1NC(Cl)=O RUGHVYVBGOKCSZ-UHFFFAOYSA-N 0.000 description 1
- DCAMJLLTTNXMNX-UHFFFAOYSA-N n-(4-fluoro-2-methylphenyl)carbamoyl chloride Chemical compound CC1=CC(F)=CC=C1NC(Cl)=O DCAMJLLTTNXMNX-UHFFFAOYSA-N 0.000 description 1
- GQNAVBITOZJZMX-UHFFFAOYSA-N n-(4-fluoro-2-nitrophenyl)carbamoyl chloride Chemical compound [O-][N+](=O)C1=CC(F)=CC=C1NC(Cl)=O GQNAVBITOZJZMX-UHFFFAOYSA-N 0.000 description 1
- PQJOAOKXAAHJKZ-UHFFFAOYSA-N n-(4-fluorophenyl)carbamoyl chloride Chemical compound FC1=CC=C(NC(Cl)=O)C=C1 PQJOAOKXAAHJKZ-UHFFFAOYSA-N 0.000 description 1
- OJMYYQMVVXFKDT-UHFFFAOYSA-N n-[2-(trifluoromethyl)phenyl]carbamoyl chloride Chemical compound FC(F)(F)C1=CC=CC=C1NC(Cl)=O OJMYYQMVVXFKDT-UHFFFAOYSA-N 0.000 description 1
- UREXDAPKGATDPO-UHFFFAOYSA-N n-[3-(trifluoromethyl)phenyl]carbamoyl chloride Chemical compound FC(F)(F)C1=CC=CC(NC(Cl)=O)=C1 UREXDAPKGATDPO-UHFFFAOYSA-N 0.000 description 1
- XFFXXVMPYYYEED-UHFFFAOYSA-N n-[4-(trifluoromethyl)phenyl]carbamoyl chloride Chemical compound FC(F)(F)C1=CC=C(NC(Cl)=O)C=C1 XFFXXVMPYYYEED-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- JFUPZYHVNIBEDW-UHFFFAOYSA-N n-phenylcarbamothioyl chloride Chemical compound ClC(=S)NC1=CC=CC=C1 JFUPZYHVNIBEDW-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- MXQOYLRVSVOCQT-UHFFFAOYSA-N palladium;tritert-butylphosphane Chemical compound [Pd].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C MXQOYLRVSVOCQT-UHFFFAOYSA-N 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- MYHOHFDYWMPGJY-UHFFFAOYSA-N pentafluorobenzoyl chloride Chemical compound FC1=C(F)C(F)=C(C(Cl)=O)C(F)=C1F MYHOHFDYWMPGJY-UHFFFAOYSA-N 0.000 description 1
- 125000005003 perfluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000005009 perfluoropropyl group Chemical group FC(C(C(F)(F)F)(F)F)(F)* 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- OBCUTHMOOONNBS-UHFFFAOYSA-N phosphorus pentafluoride Chemical compound FP(F)(F)(F)F OBCUTHMOOONNBS-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
- 229940005642 polystyrene sulfonic acid Drugs 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000004360 trifluorophenyl group Chemical group 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
- C07C209/10—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/14—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups
- C07C209/18—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/77—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/80—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
- C07C273/1854—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas by reactions not involving the formation of the N-C(O)-N- moiety
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/40—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by nitrogen atoms not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/34—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfuric acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/21—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/38—Amides of thiocarboxylic acids
- C07C327/48—Amides of thiocarboxylic acids having carbon atoms of thiocarboxamide groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C335/20—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D201/00—Coating compositions based on unspecified macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
- H10K50/155—Hole transporting layers comprising dopants
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/623—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing five rings, e.g. pentacene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Optics & Photonics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Electroluminescent Light Sources (AREA)
- Indole Compounds (AREA)
Abstract
Description
1.下記式(1)で表されるフッ素原子含有化合物。
Arは、それぞれ独立に、下記式(8)〜(11)で表される基を表し;
ArFは、それぞれ独立に、シアノ基、塩素原子、臭素原子、ヨウ素原子、ニトロ基、炭素数1〜20のアルキル基、炭素数1〜20のフルオロアルキル基若しくは炭素数1〜20のフルオロアルコキシ基で置換されていてもよい、炭素数6〜20のフルオロアリール基;炭素数1〜20のフルオロアルキル基、炭素数3〜20のフルオロシクロアルキル基、炭素数4〜20のフルオロビシクロアルキル基、炭素数2〜20のフルオロアルケニル基若しくは炭素数2〜20のフルオロアルキニル基で置換されるとともに、シアノ基、ハロゲン原子若しくは炭素数1〜20のフルオロアルコキシ基で置換されていてもよい、炭素数6〜20のアリール基を表す。]
2.ArFが、それぞれ独立に、シアノ基、塩素原子、臭素原子、ヨウ素原子、ニトロ基、炭素数1〜20のアルキル基、炭素数1〜20のフルオロアルキル基若しくは炭素数1〜20のフルオロアルコキシ基で置換されていてもよい、3以上のフッ素原子で置換されたフェニル基、又は2−(トリフルオロメチル)フェニル基、3−(トリフルオロメチル)フェニル基、4−(トリフルオロメチル)フェニル基、4−エトキシ−3−(トリフルオロメチル)フェニル基、3−フルオロ−4−トリフルオロメチルフェニル基、4−フルオロ−3−トリフルオロメチルフェニル基、4−フルオロ−2−トリフルオロメチルフェニル基、2−フルオロ−5−(トリフルオロメチル)フェニル基、3−フルオロ−5−(トリフルオロメチル)フェニル基、3,5−ジ(トリフルオロメチル)フェニル基、2,4,6−トリ(トリフルオロメチル)フェニル基、4−(ペンタフルオロエチル)フェニル基、4−(3,3,3−トリフルオロプロピル)フェニル基、2,3,5,6−テトラフルオロ−4−トリフルオロメチルフェニル基、4−(パーフルオロビニル)フェニル基、4−(パーフルオロプロペニル)フェニル基若しくは4−(パーフルオロブテニル)フェニル基である1のフッ素原子含有化合物。
3.ArFが、同一の基である1又は2のフッ素原子含有化合物。
4.Zが、式(2)で表される基である1〜3のいずれかのフッ素原子含有化合物。
5.R2が、フェニル基である1〜4のいずれかのフッ素原子含有化合物。
6.R3〜R77が、水素原子である1〜5のいずれかのフッ素原子含有化合物。
7.1〜6のいずれかのフッ素原子含有化合物からなる電荷輸送性物質。
8.7の電荷輸送性物質及び有機溶媒を含む電荷輸送性ワニス。
9.更に、フッ素原子を含有しない電荷輸送性物質を含む8の電荷輸送性ワニス。
10.更に、ドーパントを含む8又は9の電荷輸送性ワニス。
11.8〜10のいずれかの電荷輸送性ワニスを用いて作製される電荷輸送性薄膜。
12.11の電荷輸送性薄膜を備える有機EL素子。
13.式(15)で表される化合物及び式(16)で表される化合物を反応させて式(17)で表される中間体を得る工程、
式(17)で表される中間体を還元して式(18)で表される中間体を得る工程、及び
式(18)で表される中間体と式(19)で表されるハロゲン化物とを反応させる工程
を含む下記式(1)で表されるフッ素原子含有化合物の製造方法。
本発明のフッ素原子含有化合物は、下記スキームAに示される方法によって合成することができる。
本発明のフッ素原子含有化合物は、電荷輸送性物質として、特に正孔輸送性物質として好適に使用できる。本発明において、電荷輸送性とは、導電性と同義である。電荷輸送性物質とは、それ自体に電荷輸送性があるものである。また、電荷輸送性ワニスとは、それ自体に電荷輸送性があるものでもよく、それにより得られる固形膜が電荷輸送性を有するものでもよい。
本発明の電荷輸送性ワニスは、前記フッ素原子含有化合物からなる電荷輸送性物質、及び有機溶媒を含むものである。
本発明の電荷輸送性ワニスを調製する際に用いられる有機溶媒としては、前記フッ素原子含有化合物を良好に溶解し得る高溶解性溶媒を用いることができる。
本発明の電荷輸送性ワニスは、更に、フッ素原子を含有しない電荷輸送性物質を含んでもよい。このようなフッ素原子を含有しない電荷輸送性物質としては、アニリン誘導体、チオフェン誘導体、ピロール誘導体等の電荷輸送性オリゴマーが挙げられる。前記フッ素原子を含有しない電荷輸送性オリゴマーの分子量は、通常200〜8,000であるが、電荷輸送性の高い薄膜を与えるワニスを調製する観点から、好ましくは300以上、より好ましくは400以上、より一層好ましくは500以上であり、平坦性の高い薄膜を与える均一なワニスを調製する観点から、好ましくは6,000以下であり、より好ましくは5,000以下であり、より一層好ましくは4,000以下であり、更に好ましくは3,000以下である。
本発明の電荷輸送性ワニスは、得られる薄膜の用途に応じ、その電荷輸送能の向上等を目的としてドーパントを含んでもよい。ドーパントは、ワニスに使用する少なくとも1種の溶媒に溶解するものであれば特に限定されず、無機系ドーパント、有機系ドーパントのいずれも使用できる。無機系及び有機系のドーパントは、1種単独で用いてもよく、2種以上組み合わせて用いてもよい。
本発明の電荷輸送性ワニスを基材上に塗布して乾燥させることで、基材上に電荷輸送性薄膜を形成させることができる。
本発明の電荷輸送性薄膜を用いた有機EL素子とは、一対の電極を有し、これら電極の間に発光層を担う有機層を有し、さらに陽極と発光層の間に本発明の電荷輸送性薄膜を有するものである。有機EL素子の素子構造の一例としては、陽極/正孔注入層/正孔輸送層/電子ブロック層/発光層/正孔ブロック層/電子輸送層/電子注入層/陰極が挙げられるが、これに限定されない。
(1)1H-NMR測定:Varian社製、NMR system 400NB、BRUKER社製、Ascend 500
(2)基板洗浄:長州産業(株)製、基板洗浄装置(減圧プラズマ方式)
(3)ワニスの塗布:ミカサ(株)製、スピンコーターMS-A100
(4)膜厚測定:(株)小坂研究所製、微細形状測定機サーフコーダET-4000
(5)素子の作製:長州産業(株)製、多機能蒸着装置システムC-E2L1G1-N
(6)素子の電流密度の測定:(有)テック・ワールド製、I-V-L測定システム
1H-NMR (400MHz, DMSO-d6 ) δ[ppm]: 8.76(d, J=1.6Hz, 2H), 8.32(d, J=7.6Hz, 2H), 8.18-8.20(m, 4H), 8.14(d, J=8.0Hz, 2H), 7.89-7.94(m, 4H), 7.59-7.74(m, 14H), 7.52(t, J=7.2Hz, 2H), 7.35-7.44(m, 6H), 7.28(t, J=8.0Hz, 2H).
1H-NMR (400MHz, DMSO-d6) δ[ppm]: 8.63(d, J=1.6Hz, 2H), 8.39(d, J=8.0Hz, 2H), 8.12(d, J=8.0Hz, 2H), 7.92(dd, J=8.0, 1.6Hz, 2H), 7.88(s, 2H), 7.64-7.78(m, 16H), 7.54-7.58(m, 2H), 7.30-7.48(m, 12H).
1H-NMR (400MHz, THF-d8) δ[ppm]: 8.19(d, J=9.2Hz, 4H), 8.11-8.15(m, 6H), 7.90-7.95(m, 8H), 7.68(d, J=8.8Hz, 4H), 7.64(d, J=9.2Hz, 4H), 7.34-7.42(m, 8H), 7.21-7.25(m, 4H).
1H-NMR (400MHz, DMSO-d6) δ[ppm]: 10.63(s, 2H), 8.23(d, J=8.0Hz, 4H), 8.15(d, J=8.0Hz, 2H), 7.96(d, J=8.8Hz, 4H), 7.87-7.90(m, 4H), 7.69(d, J=8.8Hz, 6H), 7.64(d, J=8.8Hz, 4H), 7.39-7.44(m, 8H), 7.33(d, J=8.8Hz, 4H), 7.25-7.29(m, 4H).
1H-NMR (400MHz, DMSO-d6) δ[ppm]: 8.26(d, J=8.0Hz, 4H), 8.18(d, J=8.4Hz, 2H), 8.14(d, J=8.8Hz, 4H), 7.94-7.96(m, 6H), 7.85(d, J=8.4Hz, 2H), 7.76(t, J=8.0Hz, 2H), 7.61-7.63(m, 2H), 7.57(d, J=8.8Hz, 4H), 7.41-7.44(m, 8H), 7.28-7.32(m, 4H).
1H-NMR (400MHz, DMSO-d6) δ[ppm]: 10.59(s, 2H), 8.26(d, J=7.6Hz, 4H), 8.11(d, J=8.4Hz, 2H), 7.82-7.93(m, 8H), 7.76(t, J=7.6Hz, 2H), 7.66-7.73(m, 2H), 7.59-7.63(m, 6H), 7.42-7.47(m, 8H), 7.26-7.33(m, 8H).
1H-NMR (400MHz, THF-d8) δ[ppm]: 8.11(d, J=9.2Hz, 4H), 7.95(d, J=8.0Hz, 2H), 7.69-7.73(m, 4H), 7.54(d, J=8.8Hz, 4H), 7.47(d, J=8.8Hz, 4H), 7.20-7.25(m, 8H), 7.04-7.07(m, 12H), 6.99(t, J=7.2Hz, 4H).
1H-NMR(400MHz,DMSO-d6) δ[ppm]: 10.59(s, 2H), 7.98(d, J=8.0Hz, 2H), 7.64-7.70(m, 6H), 7.55-7.58(m, 8H), 7.25-7.29(m, 8H), 7.21(d, J=8.8Hz, 4H), 6.98-7.04(m, 16H).
[実施例5]電荷輸送性ワニスAの調製
フッ素原子含有化合物A150mgを、N,N−ジメチルイソブチルアミド(DMIB)5gに溶解させて攪拌し、得られた溶液を孔径0.2μmのポリテトラフルオロエチレン(PTFE)製フィルターを用いてろ過し、電荷輸送性ワニスAを得た。
フッ素原子含有化合物B150mgを、DMIB5gに溶解させて攪拌し、得られた溶液を孔径0.2μmのPTFE製フィルターを用いてろ過し、電荷輸送性ワニスBを得た。
フッ素原子含有化合物C100mgを、1,3−ジメチル−2−イミダゾリジノン(DMI)1.65g、2,3−ブタンジオール(2,3−BD)2g及びジプロピレングリコールモノメチルエーテル(DPM)1.35gの混合溶媒に溶解させて攪拌し、得られた溶液を孔径0.2μmのPTFE製フィルターを用いてろ過し、電荷輸送性ワニスCを得た。
フッ素原子含有化合物D100mgを、DMI1.65g、2,3−BD2g及びDPM1.35gの混合溶媒に溶解させて攪拌し、得られた溶液を孔径0.2μmのPTFE製フィルターを用いてろ過し、電荷輸送性ワニスDを得た。
下記式で表されるTFBポリマー(Luminescence Technology社製LT-N148)50mgを、3−フェノキシトルエン2.5g及びシクロヘキシルベンゼン2.5gの混合溶媒に溶解させて攪拌し、得られた溶液を孔径0.2μmのPTFE製フィルターを用いてろ過し、電荷輸送性ワニスEを得た。
以下の実施例及び比較例において、ITO基板としては、ITOが表面上に膜厚150nmでパターニングされた25mm×25mm×0.7tのガラス基板を用い、使用前にO2プラズマ洗浄装置(150W、30秒間)によって表面上の不純物を除去したものを使用した。
[実施例9]
電荷輸送性ワニスAを、スピンコーターを用いてITO基板に塗布した後、大気下で、80℃で1分間仮焼成をし、次いで230℃で15分間本焼成をし、ITO基板上に30nmの薄膜を形成した。
その上に、蒸着装置(真空度2.0×10-5Pa)を用いてアルミニウムの薄膜を積層し、HODを得た。蒸着は、蒸着レート0.2nm/秒の条件で行った。アルミニウムの薄膜の膜厚は、80nmとした。
なお、空気中の酸素、水等の影響による特性劣化を防止するため、HODは封止基板により封止した後、その特性を評価した。封止は、以下の手順で行った。
酸素濃度2ppm以下、露点−85℃以下の窒素雰囲気中で、SLDを封止基板の間に収め、封止基板を接着材((株)MORESCO製モレスコモイスチャーカットWB90US(P))により貼り合わせた。この際、捕水剤(ダイニック(株)製HD-071010W-40)をSLDと共に封止基板内に収めた。貼り合わせた封止基板に対し、UV光を照射(波長365nm、照射量6,000mJ/cm2)した後、80℃で1時間、アニーリング処理して接着材を硬化させた。
電荷輸送性ワニスAのかわりに、それぞれ電荷輸送性ワニスB〜Dを用いた以外は、実施例9と同様の方法でHODを作製した。
電荷輸送性ワニスAのかわりに電荷輸送性ワニスEを用いた以外は、実施例9と同様の方法でHODを作製した。
[実施例13]
Al/Nd基板として、Al/Ndが表面上に膜厚150nmでパターニングされた25mm×25mm×0.7tのガラス基板を用い、使用前にO2プラズマ洗浄装置(150W、30秒間)によって表面上の不純物を除却した。続いて、電荷輸送性ワニスAを、スピンコーターを用いてAl/Nd基板に塗布した後、大気下で、80℃で1分間仮焼成をし、次いで230℃で15分間本焼成をし、Al/Nd基板上に30nmの薄膜を形成した。
その上に、蒸着装置(真空度2.0×10-5Pa)を用いてアルミニウムの薄膜を積層し、EODを得た。蒸着は、蒸着レート0.2nm/秒の条件で行った。アルミニウムの薄膜の膜厚は、80nmとした。
なお、空気中の酸素、水等の影響による特性劣化を防止するため、EODは封止基板により封止した後、その特性を評価した。封止は前記と同様の方法で行った。
電荷輸送性ワニスAのかわりに、それぞれ電荷輸送性ワニスB〜Dを用いた以外は、実施例13と同様の方法でEODを作製した。
電荷輸送性ワニスAのかわりに電荷輸送性ワニスEを用いた以外は、実施例13と同様の方法でEODを作製した。
Claims (13)
- 下記式(1)で表されるフッ素原子含有化合物。
Arは、それぞれ独立に、下記式(8)〜(11)で表される基を表し;
ArFは、それぞれ独立に、シアノ基、塩素原子、臭素原子、ヨウ素原子、ニトロ基、炭素数1〜20のアルキル基、炭素数1〜20のフルオロアルキル基若しくは炭素数1〜20のフルオロアルコキシ基で置換されていてもよい、炭素数6〜20のフルオロアリール基;炭素数1〜20のフルオロアルキル基、炭素数3〜20のフルオロシクロアルキル基、炭素数4〜20のフルオロビシクロアルキル基、炭素数2〜20のフルオロアルケニル基若しくは炭素数2〜20のフルオロアルキニル基で置換されるとともに、シアノ基、ハロゲン原子若しくは炭素数1〜20のフルオロアルコキシ基で置換されていてもよい、炭素数6〜20のアリール基を表す。] - ArFが、それぞれ独立に、シアノ基、塩素原子、臭素原子、ヨウ素原子、ニトロ基、炭素数1〜20のアルキル基、炭素数1〜20のフルオロアルキル基若しくは炭素数1〜20のフルオロアルコキシ基で置換されていてもよい、3以上のフッ素原子で置換されたフェニル基、又は2−(トリフルオロメチル)フェニル基、3−(トリフルオロメチル)フェニル基、4−(トリフルオロメチル)フェニル基、4−エトキシ−3−(トリフルオロメチル)フェニル基、3−フルオロ−4−トリフルオロメチルフェニル基、4−フルオロ−3−トリフルオロメチルフェニル基、4−フルオロ−2−トリフルオロメチルフェニル基、2−フルオロ−5−(トリフルオロメチル)フェニル基、3−フルオロ−5−(トリフルオロメチル)フェニル基、3,5−ジ(トリフルオロメチル)フェニル基、2,4,6−トリ(トリフルオロメチル)フェニル基、4−(ペンタフルオロエチル)フェニル基、4−(3,3,3−トリフルオロプロピル)フェニル基、2,3,5,6−テトラフルオロ−4−トリフルオロメチルフェニル基、4−(パーフルオロビニル)フェニル基、4−(パーフルオロプロペニル)フェニル基若しくは4−(パーフルオロブテニル)フェニル基である請求項1記載のフッ素原子含有化合物。
- ArFが、同一の基である請求項1又は2記載のフッ素原子含有化合物。
- Zが、式(2)で表される基である請求項1〜3のいずれか1項記載のフッ素原子含有化合物。
- R2が、フェニル基である請求項1〜4のいずれか1項記載のフッ素原子含有化合物。
- R3〜R77が、水素原子である請求項1〜5のいずれか1項記載のフッ素原子含有化合物。
- 請求項1〜6のいずれか1項記載のフッ素原子含有化合物からなる電荷輸送性物質。
- 請求項7記載の電荷輸送性物質及び有機溶媒を含む電荷輸送性ワニス。
- 更に、フッ素原子を含有しない電荷輸送性物質を含む請求項8記載の電荷輸送性ワニス。
- 更に、ドーパントを含む請求項8又は9記載の電荷輸送性ワニス。
- 請求項8〜10のいずれか1項記載の電荷輸送性ワニスを用いて作製される電荷輸送性薄膜。
- 請求項11記載の電荷輸送性薄膜を備える有機エレクトロルミネッセンス素子。
- 式(15)で表される化合物及び式(16)で表される化合物を反応させて式(17)で表される中間体を得る工程、
式(17)で表される中間体を還元して式(18)で表される中間体を得る工程、及び
式(18)で表される中間体と式(19)で表されるハロゲン化物とを反応させる工程
を含む下記式(1)で表されるフッ素原子含有化合物の製造方法。
Arは、それぞれ独立に、下記式(8)〜(11)で表される基を表し;
ArFは、それぞれ独立に、シアノ基、塩素原子、臭素原子、ヨウ素原子、ニトロ基、炭素数1〜20のアルキル基、炭素数1〜20のフルオロアルキル基若しくは炭素数1〜20のフルオロアルコキシ基で置換されていてもよい、炭素数6〜20のフルオロアリール基;炭素数1〜20のフルオロアルキル基、炭素数3〜20のフルオロシクロアルキル基、炭素数4〜20のフルオロビシクロアルキル基、炭素数2〜20のフルオロアルケニル基若しくは炭素数2〜20のフルオロアルキニル基で置換されるとともに、シアノ基、ハロゲン原子若しくは炭素数1〜20のフルオロアルコキシ基で置換されていてもよい、炭素数6〜20のアリール基を表し;
Xは、ハロゲン原子又は擬ハロゲン基を表す。]
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2016005375 | 2016-01-14 | ||
JP2016005375 | 2016-01-14 | ||
PCT/JP2017/000545 WO2017122649A1 (ja) | 2016-01-14 | 2017-01-11 | フッ素原子含有化合物及びその利用 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPWO2017122649A1 true JPWO2017122649A1 (ja) | 2018-11-01 |
JP6954123B2 JP6954123B2 (ja) | 2021-10-27 |
Family
ID=59311760
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2017561119A Active JP6954123B2 (ja) | 2016-01-14 | 2017-01-11 | フッ素原子含有化合物及びその利用 |
Country Status (7)
Country | Link |
---|---|
US (1) | US10336686B2 (ja) |
EP (1) | EP3404017B1 (ja) |
JP (1) | JP6954123B2 (ja) |
KR (1) | KR20180101510A (ja) |
CN (1) | CN108698982B (ja) |
TW (1) | TWI726036B (ja) |
WO (1) | WO2017122649A1 (ja) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPWO2020203594A1 (ja) * | 2019-03-29 | 2020-10-08 | ||
CN115703718A (zh) * | 2021-08-09 | 2023-02-17 | 华为技术有限公司 | 二胺单体化合物及制备方法、树脂、柔性薄膜和电子设备 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20140078096A (ko) * | 2012-12-17 | 2014-06-25 | 에스에프씨 주식회사 | 플루오렌구조를 포함하는 방향족 아민 유도체 및 이를 포함하는 유기 발광 소자 |
KR20140128878A (ko) * | 2013-04-29 | 2014-11-06 | 에스에프씨 주식회사 | 방향족 아민 유도체 및 이를 포함하는 유기전계발광소자 |
WO2015041416A1 (ko) * | 2013-09-17 | 2015-03-26 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물을 이용한 유기전기소자 및 그 전자 장치 |
WO2015174682A1 (ko) * | 2014-05-13 | 2015-11-19 | 에스에프씨 주식회사 | 방향족아민기를 포함하는 헤테로고리 화합물및 이를 포함하는 유기 발광 소자 |
JP2017153776A (ja) * | 2016-03-03 | 2017-09-07 | 株式会社ユニバーサルエンターテインメント | 情報提供システムおよび情報提供装置 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7862747B2 (en) | 2004-08-31 | 2011-01-04 | Nissan Chemical Industries, Ltd. | Arylsulfonic acid compound and use thereof as electron-acceptor material |
JP4765589B2 (ja) | 2005-12-02 | 2011-09-07 | 東洋インキScホールディングス株式会社 | カルバゾリル基を有するフルオレン化合物およびその用途 |
JP2008027646A (ja) | 2006-07-19 | 2008-02-07 | Toppan Printing Co Ltd | 有機el素子の正孔輸送層形成用塗布装置及び有機el素子の製造方法 |
WO2008032616A1 (en) | 2006-09-13 | 2008-03-20 | Nissan Chemical Industries, Ltd. | Oligoaniline compounds |
KR101557109B1 (ko) | 2007-04-12 | 2015-10-02 | 닛산 가가쿠 고교 가부시키 가이샤 | 올리고아닐린 화합물 |
JP5488473B2 (ja) | 2008-11-19 | 2014-05-14 | 日産化学工業株式会社 | 電荷輸送性ワニス |
CN102408342B (zh) * | 2011-07-22 | 2014-06-18 | 中山大学 | 具有大共轭结构的含芴功能二胺单体及其合成方法和应用 |
KR102030354B1 (ko) | 2014-05-13 | 2019-10-10 | 에스에프씨주식회사 | 방향족 아민기를 포함하는 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자 |
CN107710440B (zh) * | 2015-06-15 | 2019-12-24 | 日产化学工业株式会社 | 电荷传输性清漆和有机电致发光元件 |
-
2017
- 2017-01-11 WO PCT/JP2017/000545 patent/WO2017122649A1/ja active Application Filing
- 2017-01-11 KR KR1020187023099A patent/KR20180101510A/ko not_active Application Discontinuation
- 2017-01-11 EP EP17738403.9A patent/EP3404017B1/en not_active Expired - Fee Related
- 2017-01-11 JP JP2017561119A patent/JP6954123B2/ja active Active
- 2017-01-11 US US16/070,111 patent/US10336686B2/en not_active Expired - Fee Related
- 2017-01-11 CN CN201780006464.5A patent/CN108698982B/zh active Active
- 2017-01-13 TW TW106101243A patent/TWI726036B/zh active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20140078096A (ko) * | 2012-12-17 | 2014-06-25 | 에스에프씨 주식회사 | 플루오렌구조를 포함하는 방향족 아민 유도체 및 이를 포함하는 유기 발광 소자 |
KR20140128878A (ko) * | 2013-04-29 | 2014-11-06 | 에스에프씨 주식회사 | 방향족 아민 유도체 및 이를 포함하는 유기전계발광소자 |
WO2015041416A1 (ko) * | 2013-09-17 | 2015-03-26 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물을 이용한 유기전기소자 및 그 전자 장치 |
WO2015174682A1 (ko) * | 2014-05-13 | 2015-11-19 | 에스에프씨 주식회사 | 방향족아민기를 포함하는 헤테로고리 화합물및 이를 포함하는 유기 발광 소자 |
JP2017153776A (ja) * | 2016-03-03 | 2017-09-07 | 株式会社ユニバーサルエンターテインメント | 情報提供システムおよび情報提供装置 |
Also Published As
Publication number | Publication date |
---|---|
EP3404017B1 (en) | 2020-05-13 |
US20190031600A1 (en) | 2019-01-31 |
TWI726036B (zh) | 2021-05-01 |
EP3404017A1 (en) | 2018-11-21 |
KR20180101510A (ko) | 2018-09-12 |
EP3404017A4 (en) | 2019-01-09 |
WO2017122649A1 (ja) | 2017-07-20 |
CN108698982B (zh) | 2021-07-16 |
JP6954123B2 (ja) | 2021-10-27 |
US10336686B2 (en) | 2019-07-02 |
CN108698982A (zh) | 2018-10-23 |
TW201738201A (zh) | 2017-11-01 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6597642B2 (ja) | 電荷輸送性薄膜形成用ワニス | |
TWI627242B (zh) | 電荷輸送性塗料以及有機電致發光元件 | |
JP2020040962A (ja) | N,n,n′,n′−テトラフェニルベンジジン化合物 | |
JP6460093B2 (ja) | オリゴアニリン誘導体、電荷輸送性ワニス及び有機エレクトロルミネッセンス素子 | |
JP6954123B2 (ja) | フッ素原子含有化合物及びその利用 | |
JP6566032B2 (ja) | 電荷輸送性ワニス及び有機エレクトロルミネッセンス素子 | |
JP6011723B2 (ja) | トリフェニルアミン誘導体およびその利用 | |
JP2023126469A (ja) | 電荷輸送性ワニス | |
JP6432593B2 (ja) | 電荷輸送性ワニス | |
WO2020203594A1 (ja) | フルオレン誘導体及びその利用 | |
JP7491302B2 (ja) | アリールアミン化合物およびその利用 | |
JP7322884B2 (ja) | 重合体及びその利用 | |
JP6927214B2 (ja) | 電荷輸送性薄膜形成用ワニス | |
JP6601405B2 (ja) | 電荷輸送性ワニス |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20191122 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20200630 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20200807 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20210202 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20210309 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20210831 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20210913 |
|
R151 | Written notification of patent or utility model registration |
Ref document number: 6954123 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R151 |