TW294662B - - Google Patents
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- TW294662B TW294662B TW085100976A TW85100976A TW294662B TW 294662 B TW294662 B TW 294662B TW 085100976 A TW085100976 A TW 085100976A TW 85100976 A TW85100976 A TW 85100976A TW 294662 B TW294662 B TW 294662B
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- TW
- Taiwan
- Prior art keywords
- alkyl
- substituted
- alkoxy
- group
- formula
- Prior art date
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- -1 phenoxy, phenylsulfenyl Chemical group 0.000 claims description 205
- 229910000071 diazene Inorganic materials 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 36
- 238000006243 chemical reaction Methods 0.000 claims description 35
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 claims description 31
- 239000007789 gas Substances 0.000 claims description 25
- 239000002585 base Substances 0.000 claims description 22
- 238000011049 filling Methods 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical class 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 239000003054 catalyst Substances 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
- 150000002466 imines Chemical class 0.000 claims description 13
- 239000003701 inert diluent Substances 0.000 claims description 13
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 10
- 239000007800 oxidant agent Substances 0.000 claims description 10
- 150000000000 tetracarboxylic acids Chemical class 0.000 claims description 10
- 238000005859 coupling reaction Methods 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 238000006467 substitution reaction Methods 0.000 claims description 9
- 239000007850 fluorescent dye Substances 0.000 claims description 8
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 230000000269 nucleophilic effect Effects 0.000 claims description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 6
- 230000008878 coupling Effects 0.000 claims description 6
- 238000010168 coupling process Methods 0.000 claims description 6
- 229910052763 palladium Inorganic materials 0.000 claims description 6
- 239000000049 pigment Substances 0.000 claims description 6
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 5
- 125000005110 aryl thio group Chemical group 0.000 claims description 5
- 125000004104 aryloxy group Chemical group 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 239000012429 reaction media Substances 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 239000003513 alkali Chemical group 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 150000007529 inorganic bases Chemical class 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- 230000001590 oxidative effect Effects 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000006158 tetracarboxylic acid group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 241000282376 Panthera tigris Species 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 239000001301 oxygen Substances 0.000 claims 3
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical group N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 2
- 150000001335 aliphatic alkanes Chemical group 0.000 claims 2
- 150000002815 nickel Chemical class 0.000 claims 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 2
- 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 claims 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 2
- PCTMTFRHKVHKIS-BMFZQQSSSA-N (1s,3r,4e,6e,8e,10e,12e,14e,16e,18s,19r,20r,21s,25r,27r,30r,31r,33s,35r,37s,38r)-3-[(2r,3s,4s,5s,6r)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-19,25,27,30,31,33,35,37-octahydroxy-18,20,21-trimethyl-23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10 Chemical compound C1C=C2C[C@@H](OS(O)(=O)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2.O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 PCTMTFRHKVHKIS-BMFZQQSSSA-N 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims 1
- OUBCVOQKBNGZDY-UHFFFAOYSA-N 1-sulfidopyrimidin-1-ium Chemical group [S-][N+]1=CC=CN=C1 OUBCVOQKBNGZDY-UHFFFAOYSA-N 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- MEVHTHLQPUQANE-UHFFFAOYSA-N aziridine-2,3-dione Chemical compound O=C1NC1=O MEVHTHLQPUQANE-UHFFFAOYSA-N 0.000 claims 1
- 150000004985 diamines Chemical class 0.000 claims 1
- HALQELOKLVRWRI-VDBOFHIQSA-N doxycycline hyclate Chemical group O.[Cl-].[Cl-].CCO.O=C1C2=C(O)C=CC=C2[C@H](C)[C@@H]2C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H]([NH+](C)C)[C@@H]1[C@H]2O.O=C1C2=C(O)C=CC=C2[C@H](C)[C@@H]2C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H]([NH+](C)C)[C@@H]1[C@H]2O HALQELOKLVRWRI-VDBOFHIQSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical compound S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 claims 1
- 125000004149 thio group Chemical group *S* 0.000 claims 1
- 239000002023 wood Substances 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 17
- 238000002360 preparation method Methods 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 10
- 229910052799 carbon Inorganic materials 0.000 description 10
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 10
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 9
- 230000000875 corresponding effect Effects 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 150000003949 imides Chemical class 0.000 description 8
- 239000000203 mixture Chemical group 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 230000035484 reaction time Effects 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 150000008064 anhydrides Chemical class 0.000 description 7
- 230000001681 protective effect Effects 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000005893 bromination reaction Methods 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000005658 halogenation reaction Methods 0.000 description 6
- 229910000000 metal hydroxide Inorganic materials 0.000 description 6
- 150000004692 metal hydroxides Chemical class 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 125000002524 organometallic group Chemical group 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 150000003141 primary amines Chemical class 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 4
- 229910052723 transition metal Inorganic materials 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000002309 gasification Methods 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- 125000005553 heteroaryloxy group Chemical group 0.000 description 3
- 125000005368 heteroarylthio group Chemical group 0.000 description 3
- 150000002463 imidates Chemical class 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 238000009434 installation Methods 0.000 description 3
- 235000012054 meals Nutrition 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 235000021286 stilbenes Nutrition 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical class C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 2
- 101150041968 CDC13 gene Proteins 0.000 description 2
- 101100037762 Caenorhabditis elegans rnh-2 gene Proteins 0.000 description 2
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 2
- 239000005751 Copper oxide Substances 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000010306 acid treatment Methods 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 239000012300 argon atmosphere Substances 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 239000003849 aromatic solvent Substances 0.000 description 2
- 230000031709 bromination Effects 0.000 description 2
- DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 229910000431 copper oxide Inorganic materials 0.000 description 2
- 150000002013 dioxins Chemical class 0.000 description 2
- 125000003438 dodecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- GPTFURBXHJWNHR-UHFFFAOYSA-N protopine Chemical group C1=C2C(=O)CC3=CC=C4OCOC4=C3CN(C)CCC2=CC2=C1OCO2 GPTFURBXHJWNHR-UHFFFAOYSA-N 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 150000003573 thiols Chemical class 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 description 1
- RVHSTXJKKZWWDQ-UHFFFAOYSA-N 1,1,1,2-tetrabromoethane Chemical compound BrCC(Br)(Br)Br RVHSTXJKKZWWDQ-UHFFFAOYSA-N 0.000 description 1
- QXSZNDIIPUOQMB-UHFFFAOYSA-N 1,1,2,2-tetrabromoethane Chemical compound BrC(Br)C(Br)Br QXSZNDIIPUOQMB-UHFFFAOYSA-N 0.000 description 1
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- 239000011701 zinc Substances 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- XDWXRAYGALQIFG-UHFFFAOYSA-L zinc;propanoate Chemical compound [Zn+2].CCC([O-])=O.CCC([O-])=O XDWXRAYGALQIFG-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/18—Ring systems of four or more rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/62—Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Cosmetics (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19501576 | 1995-01-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW294662B true TW294662B (OSRAM) | 1997-01-01 |
Family
ID=7751878
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW085100976A TW294662B (OSRAM) | 1995-01-20 | 1996-01-26 |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US5986099A (OSRAM) |
| EP (1) | EP0804507B1 (OSRAM) |
| JP (1) | JP4054377B2 (OSRAM) |
| CN (2) | CN1089784C (OSRAM) |
| DE (1) | DE59601770D1 (OSRAM) |
| FI (1) | FI973056A7 (OSRAM) |
| TW (1) | TW294662B (OSRAM) |
| WO (1) | WO1996022332A1 (OSRAM) |
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19622673A1 (de) * | 1996-06-05 | 1997-12-11 | Basf Ag | Verfahren zur Herstellung von Perylen-3,4-dicarbonsäureimiden |
| JPH10183112A (ja) * | 1996-12-27 | 1998-07-14 | Sony Corp | 電界発光素子 |
| US6166210A (en) * | 1997-12-15 | 2000-12-26 | Ciba Specialty Chemicals Corporation | Perylene imide monocarboxylic acids |
| DE19805121A1 (de) | 1998-02-09 | 1999-08-12 | Basf Ag | Verfahren zur Herstellung farbstoffenthaltender, wässriger Polymerisatdispersionen |
| WO2000052099A1 (en) * | 1999-02-26 | 2000-09-08 | Ciba Specialty Chemicals Holding Inc. | Bichromophoric perylene-3,4-dicarboximides |
| DE19940708A1 (de) | 1999-08-27 | 2001-03-01 | Basf Ag | Thermochrome Rylenfarbstoffe |
| DE19949382A1 (de) | 1999-10-13 | 2001-04-19 | Basf Ag | Verwendung feinteiliger, farbstoffhaltiger Polymerisate PF als farbgebenden Bestandteil in kosmetischen Mitteln |
| DE10108156A1 (de) | 2001-02-20 | 2002-08-29 | Basf Ag | Rylenderivate |
| DE10108601A1 (de) * | 2001-02-22 | 2002-09-05 | Basf Ag | Thermochrome Rylenfarbstoffe |
| PT1379577E (pt) | 2001-03-23 | 2004-11-30 | Solutia Inc | Controlo da radiacao solar em vidros de seguranca laminados |
| DE50203504D1 (de) * | 2001-03-23 | 2005-08-04 | Basf Ag | Tert.-alkylphenoxysubstituierte polycyclische verbindungen |
| US6638585B2 (en) * | 2002-01-25 | 2003-10-28 | Hewlett-Packard Development Company, L.P. | Coated media for improved output tray stacking performance |
| DE10243906A1 (de) | 2002-09-20 | 2004-04-01 | Basf Ag | 9-Cyanosubstituierte Perylen-3,4-dicarbonsäuremonoimide |
| WO2005089094A2 (en) * | 2003-11-21 | 2005-09-29 | The Board Of Regents Of The University And Community College System Of Nevada | Materials and methods for the preparation of anisotropically-ordered solids |
| JP4921982B2 (ja) * | 2004-01-26 | 2012-04-25 | ノースウエスタン ユニバーシティ | ペリレンｎ型半導体及び関連装置 |
| DE102004048729A1 (de) * | 2004-10-05 | 2006-04-06 | Basf Ag | Verfahren zur Herstellung von halogenierten Rylencarbonsäureimiden |
| DE102005018241A1 (de) | 2005-04-19 | 2006-10-26 | Basf Ag | Hexarylen- und Pentarylentetracarbonsäurediimide |
| DE102005021362A1 (de) * | 2005-05-04 | 2006-11-09 | Basf Ag | Terrylen- und Quaterrylenderivate |
| DE102005032583A1 (de) | 2005-07-11 | 2007-01-25 | Basf Ag | Substituierte Rylenderivate |
| DE102005037115A1 (de) | 2005-08-03 | 2007-02-08 | Basf Ag | Mehrfachchromophore |
| JP2009528277A (ja) | 2006-02-17 | 2009-08-06 | ビーエーエスエフ ソシエタス・ヨーロピア | フッ素化されたリレンテトラカルボン酸誘導体及びそれらの使用 |
| EP1843407A1 (de) * | 2006-04-07 | 2007-10-10 | Basf Aktiengesellschaft | Flüssig-kristalline Rylentetracarbonsäurederivate und deren Verwendung |
| ATE520158T1 (de) * | 2006-05-04 | 2011-08-15 | Basf Se | Verfahren zum herstellen organischer feldeffekttransistoren |
| US20070259475A1 (en) * | 2006-05-04 | 2007-11-08 | Basf Aktiengesellschaft | Method for producing organic field-effect transistors |
| WO2007146250A2 (en) * | 2006-06-12 | 2007-12-21 | Northwestern University | Naphthalene-based semiconductor materials and methods of preparing and use thereof |
| EP2089398A2 (en) * | 2006-10-25 | 2009-08-19 | Polyera Corporation | Organic semiconductor materials and methods of preparing and use thereof |
| JP2010508326A (ja) * | 2006-11-02 | 2010-03-18 | ビーエーエスエフ ソシエタス・ヨーロピア | ペンタリレンテトラカルボン酸ジイミド及びヘキサリレンテトラカルボン酸ジイミド並びにそれらの製造 |
| US7902363B2 (en) * | 2006-11-17 | 2011-03-08 | Polyera Corporation | Diimide-based semiconductor materials and methods of preparing and using the same |
| CN101622253B (zh) * | 2007-01-08 | 2015-04-29 | 破立纪元有限公司 | 用于制备基于芳烃-双（二羧酰亚胺）的半导体材料的方法和用于制备它们的相关中间体 |
| WO2008091670A2 (en) * | 2007-01-24 | 2008-07-31 | Polyera Corporation | Organic semiconductor materials and precursors thereof |
| DE102007015261A1 (de) | 2007-03-27 | 2008-10-02 | Aacure Aadhesives Gmbh | Reaktivmasse und Verfahren zur Aufbringung hierfür |
| US20100224998A1 (en) * | 2008-06-26 | 2010-09-09 | Carben Semicon Limited | Integrated Circuit with Ribtan Interconnects |
| EP2166040A1 (en) | 2008-09-22 | 2010-03-24 | Radiant Color N.V. | Novel lipophilic fluorescent dyes and a process for their production |
| ES2730948T3 (es) | 2010-12-03 | 2019-11-13 | 3G Mermet Corp | Composición reflectante del infrarrojo cercano y cubiertas para aberturas arquitectónicas que incorporan la misma |
| DE102011007196A1 (de) | 2011-04-12 | 2012-10-18 | Evonik Degussa Gmbh | Verfahren zur Herstellung eines Verbundes aus einem Polyamidformteil und einem Methacrylatcopolymer-Formteil |
| EP2867234A2 (en) * | 2012-06-29 | 2015-05-06 | Basf Se | Substituted terrylene and quaterrylene derivatives and the use as semiconductors thereof |
| US9655980B2 (en) | 2012-08-01 | 2017-05-23 | University of Pittsburgh—of the Commonwealth System of Higher Education | Theranostic platform for targeted cancer therapy and drug delivery monitoring |
| CN104672140A (zh) * | 2014-11-21 | 2015-06-03 | 华中科技大学 | 一种多取代苝类衍生物及其制备方法 |
| EP3816238B9 (en) | 2019-11-04 | 2023-06-21 | Textilchemie Dr. Petry Gmbh | Polyparaperylene derivatives and methods for making same |
| EP3858946A1 (en) | 2020-01-29 | 2021-08-04 | Basf Se | New rylene dicarboximides |
| US20230361302A1 (en) * | 2021-01-07 | 2023-11-09 | Lg Energy Solution, Ltd. | Positive electrode additive for lithium secondary battery, positive electrode active material comprising same, positive electrode, and lithium secondary battery |
| EP4444700A1 (en) | 2021-12-09 | 2024-10-16 | Basf Se | Terrylene diimide and quaterrylene diimide colorants |
| CN114573412B (zh) * | 2022-02-23 | 2023-12-26 | 杭州凯名庞德生物科技有限公司 | 一种苯并苝的制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1715430A (en) * | 1922-12-27 | 1929-06-04 | Grasselli Dyestuff Corp | Manufacture of vat dyestuffs |
| DE3631678A1 (de) * | 1986-09-18 | 1988-03-24 | Basf Ag | Tetrachlorperylen-3,4,9,10-tetracarbonsaeurediimidpigment und dessen verwendung |
| TW215132B (en) * | 1992-09-21 | 1993-10-21 | Advanced Micro Devices Inc | Method and apparatus for the elimination of metal voids and metal lines of a semiconductor device |
| DE4236885A1 (de) * | 1992-10-31 | 1994-05-05 | Basf Ag | Quaterrylentetracarbonsäureimide |
-
1996
- 1996-01-12 DE DE59601770T patent/DE59601770D1/de not_active Expired - Lifetime
- 1996-01-12 EP EP96900944A patent/EP0804507B1/de not_active Expired - Lifetime
- 1996-01-12 US US08/860,928 patent/US5986099A/en not_active Expired - Fee Related
- 1996-01-12 WO PCT/EP1996/000118 patent/WO1996022332A1/de not_active Ceased
- 1996-01-12 JP JP52202496A patent/JP4054377B2/ja not_active Expired - Fee Related
- 1996-01-12 CN CN96191512A patent/CN1089784C/zh not_active Expired - Lifetime
- 1996-01-26 TW TW085100976A patent/TW294662B/zh not_active IP Right Cessation
-
1997
- 1997-07-18 FI FI973056A patent/FI973056A7/fi unknown
-
1999
- 1999-06-18 US US09/335,535 patent/US6124458A/en not_active Expired - Fee Related
-
2001
- 2001-12-13 CN CNB011435720A patent/CN1263744C/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0804507B1 (de) | 1999-04-28 |
| EP0804507A1 (de) | 1997-11-05 |
| CN1169155A (zh) | 1997-12-31 |
| CN1263744C (zh) | 2006-07-12 |
| FI973056A0 (fi) | 1997-07-18 |
| CN1089784C (zh) | 2002-08-28 |
| US5986099A (en) | 1999-11-16 |
| JP4054377B2 (ja) | 2008-02-27 |
| US6124458A (en) | 2000-09-26 |
| WO1996022332A1 (de) | 1996-07-25 |
| DE59601770D1 (de) | 1999-06-02 |
| JPH11502546A (ja) | 1999-03-02 |
| FI973056A7 (fi) | 1997-07-18 |
| CN1413988A (zh) | 2003-04-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Annulment or lapse of patent due to non-payment of fees |