JP2010510228A5 - - Google Patents
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- Publication number
- JP2010510228A5 JP2010510228A5 JP2009537237A JP2009537237A JP2010510228A5 JP 2010510228 A5 JP2010510228 A5 JP 2010510228A5 JP 2009537237 A JP2009537237 A JP 2009537237A JP 2009537237 A JP2009537237 A JP 2009537237A JP 2010510228 A5 JP2010510228 A5 JP 2010510228A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- bis
- alkyl
- dicarboxamide
- mmol
- 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
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 381
- -1 2-ethylpropyl group Chemical group 0.000 claims description 219
- 150000001875 compounds Chemical class 0.000 claims description 139
- 239000004065 semiconductor Substances 0.000 claims description 74
- 239000000203 mixture Substances 0.000 claims description 71
- 239000010409 thin film Substances 0.000 claims description 25
- 239000000758 substrate Substances 0.000 claims description 19
- 230000005669 field effect Effects 0.000 claims description 16
- 239000002131 composite material Substances 0.000 claims description 13
- 239000003989 dielectric material Substances 0.000 claims description 13
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 11
- 125000002347 octyl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- 125000004051 hexyl group Chemical class [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
- 238000007639 printing Methods 0.000 claims description 9
- 238000005266 casting Methods 0.000 claims description 8
- 125000000484 butyl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- 239000011248 coating agent Substances 0.000 claims description 6
- 238000000576 coating method Methods 0.000 claims description 6
- 238000000151 deposition Methods 0.000 claims description 6
- 125000001147 pentyl group Chemical class C(CCCC)* 0.000 claims description 6
- 238000004528 spin coating Methods 0.000 claims description 6
- 125000003187 heptyl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- 238000007740 vapor deposition Methods 0.000 claims description 5
- 238000003618 dip coating Methods 0.000 claims description 4
- 238000005507 spraying Methods 0.000 claims description 4
- 125000005916 2-methylpentyl group Chemical group 0.000 claims description 3
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 2
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 108
- 125000000217 alkyl group Chemical group 0.000 description 96
- 125000004093 cyano group Chemical group *C#N 0.000 description 95
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 91
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 88
- 238000002360 preparation method Methods 0.000 description 72
- 239000007787 solid Substances 0.000 description 67
- 125000003118 aryl group Chemical group 0.000 description 62
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 55
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 54
- 239000000243 solution Substances 0.000 description 48
- 239000011541 reaction mixture Substances 0.000 description 46
- 238000001816 cooling Methods 0.000 description 39
- 238000001914 filtration Methods 0.000 description 38
- 235000019260 propionic acid Nutrition 0.000 description 36
- 238000000921 elemental analysis Methods 0.000 description 33
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 32
- 239000000463 material Substances 0.000 description 31
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 30
- 239000012043 crude product Substances 0.000 description 28
- 125000001188 haloalkyl group Chemical group 0.000 description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 27
- 229910002027 silica gel Inorganic materials 0.000 description 27
- 239000000741 silica gel Substances 0.000 description 27
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 26
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 26
- 125000004432 carbon atoms Chemical group C* 0.000 description 25
- 238000004587 chromatography analysis Methods 0.000 description 25
- 125000001246 bromo group Chemical group Br* 0.000 description 24
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- 238000010992 reflux Methods 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- 239000010408 film Substances 0.000 description 22
- 239000002244 precipitate Substances 0.000 description 22
- DOBRDRYODQBAMW-UHFFFAOYSA-N Copper(I) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- 125000003545 alkoxy group Chemical group 0.000 description 20
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 239000002904 solvent Substances 0.000 description 19
- 239000000725 suspension Substances 0.000 description 18
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 description 17
- 125000001072 heteroaryl group Chemical group 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 14
- 125000003342 alkenyl group Chemical group 0.000 description 14
- 229910052736 halogen Inorganic materials 0.000 description 14
- 150000002367 halogens Chemical class 0.000 description 14
- 239000008079 hexane Substances 0.000 description 14
- 238000000034 method Methods 0.000 description 13
- 239000012071 phase Substances 0.000 description 12
- 238000000746 purification Methods 0.000 description 12
- 229910052739 hydrogen Inorganic materials 0.000 description 11
- 239000003960 organic solvent Substances 0.000 description 11
- 239000000843 powder Substances 0.000 description 11
- 125000000753 cycloalkyl group Chemical group 0.000 description 10
- 150000003949 imides Chemical group 0.000 description 10
- 230000005012 migration Effects 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 229910052698 phosphorus Inorganic materials 0.000 description 10
- 125000006649 (C2-C20) alkynyl group Chemical group 0.000 description 9
- LKYXEULZVGJVTG-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH] LKYXEULZVGJVTG-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 125000000547 substituted alkyl group Chemical group 0.000 description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 8
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 8
- DAKDMXXOBUCMBK-UHFFFAOYSA-N OC(=O)[N-]C(O)=O Chemical compound OC(=O)[N-]C(O)=O DAKDMXXOBUCMBK-UHFFFAOYSA-N 0.000 description 8
- 125000003710 aryl alkyl group Chemical group 0.000 description 8
- 229910052731 fluorine Inorganic materials 0.000 description 8
- 125000005842 heteroatoms Chemical group 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 7
- 125000005915 C6-C14 aryl group Chemical group 0.000 description 7
- RAABOESOVLLHRU-UHFFFAOYSA-N Diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 7
- NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [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 7
- 125000004429 atoms Chemical group 0.000 description 7
- 239000012267 brine Substances 0.000 description 7
- 239000003990 capacitor Substances 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- 238000004440 column chromatography Methods 0.000 description 7
- 229910000071 diazene Inorganic materials 0.000 description 7
- 230000003287 optical Effects 0.000 description 7
- 229910052760 oxygen Chemical group 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
- BEKHDAJTCOSDPJ-UHFFFAOYSA-N 1,2,3,4,5-pentafluoro-6-phenylbenzene Chemical group FC1=C(F)C(F)=C(F)C(F)=C1C1=CC=CC=C1 BEKHDAJTCOSDPJ-UHFFFAOYSA-N 0.000 description 6
- GBGZXMZYCHOINO-UHFFFAOYSA-N FC1=C(F)C(CCCCCCCC)=C(F)C(F)=C1C1=CC=CC=C1 Chemical group FC1=C(F)C(CCCCCCCC)=C(F)C(F)=C1C1=CC=CC=C1 GBGZXMZYCHOINO-UHFFFAOYSA-N 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M Potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 125000004414 alkyl thio group Chemical group 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- 238000007306 functionalization reaction Methods 0.000 description 6
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 125000004043 oxo group Chemical group O=* 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 238000006467 substitution reaction Methods 0.000 description 6
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 6
- CTYWTKRLLXDAKN-UHFFFAOYSA-N C1=CC(CCCCCCCC)=CC=C1C1=C(F)C(F)=CC(F)=C1F Chemical group C1=CC(CCCCCCCC)=CC=C1C1=C(F)C(F)=CC(F)=C1F CTYWTKRLLXDAKN-UHFFFAOYSA-N 0.000 description 5
- 229910004298 SiO 2 Inorganic materials 0.000 description 5
- 125000000304 alkynyl group Chemical group 0.000 description 5
- 239000002800 charge carrier Substances 0.000 description 5
- 239000012230 colorless oil Substances 0.000 description 5
- 230000000295 complement Effects 0.000 description 5
- 235000019439 ethyl acetate Nutrition 0.000 description 5
- 229910001867 inorganic solvent Inorganic materials 0.000 description 5
- 239000003049 inorganic solvent Substances 0.000 description 5
- 239000011669 selenium Chemical group 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 4
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 description 4
- 125000006708 (C5-C14) heteroaryl group Chemical group 0.000 description 4
- FKZUJUAMRZCCRX-UHFFFAOYSA-N 1-iodo-4-octylbenzene Chemical compound CCCCCCCCC1=CC=C(I)C=C1 FKZUJUAMRZCCRX-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 4
- 125000003493 decenyl group Chemical group [H]C([*])=C([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])[H] 0.000 description 4
- 125000003709 fluoroalkyl group Chemical group 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 238000007641 inkjet printing Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 150000002829 nitrogen Chemical group 0.000 description 4
- 230000005693 optoelectronics Effects 0.000 description 4
- 239000001301 oxygen Chemical group 0.000 description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical group O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 229910052711 selenium Inorganic materials 0.000 description 4
- 238000004736 wide-angle X-ray diffraction Methods 0.000 description 4
- IQLIIURHJFOWCJ-UHFFFAOYSA-N 4-(2,3,4,5,6-pentafluorophenyl)aniline Chemical group C1=CC(N)=CC=C1C1=C(F)C(F)=C(F)C(F)=C1F IQLIIURHJFOWCJ-UHFFFAOYSA-N 0.000 description 3
- BDVBGIPKWZCKRY-UHFFFAOYSA-N 4-(2,3,5,6-tetrafluoro-4-octylphenyl)aniline Chemical group FC1=C(F)C(CCCCCCCC)=C(F)C(F)=C1C1=CC=C(N)C=C1 BDVBGIPKWZCKRY-UHFFFAOYSA-N 0.000 description 3
- 0 CC(CCC=C(C)C)CCN* Chemical compound CC(CCC=C(C)C)CCN* 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M Sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 3
- 125000005841 biaryl group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000006267 biphenyl group Chemical group 0.000 description 3
- 238000002508 contact lithography Methods 0.000 description 3
- 125000002704 decyl 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])* 0.000 description 3
- 125000006159 dianhydride group Chemical group 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000012259 ether extract Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000010931 gold Substances 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 125000005462 imide group Chemical group 0.000 description 3
- 239000012212 insulator Substances 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 125000004433 nitrogen atoms Chemical group N* 0.000 description 3
- 125000003367 polycyclic group Chemical group 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- BUGBHKTXTAQXES-UHFFFAOYSA-N selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000001187 sodium carbonate Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- PYJJCSYBSYXGQQ-UHFFFAOYSA-N trichloro(octadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[Si](Cl)(Cl)Cl PYJJCSYBSYXGQQ-UHFFFAOYSA-N 0.000 description 3
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 2
- SCCCFNJTCDSLCY-UHFFFAOYSA-N 1-iodo-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(I)C=C1 SCCCFNJTCDSLCY-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- BNOMVHZDJIXZAA-UHFFFAOYSA-N 2-methylhexan-1-amine Chemical compound CCCCC(C)CN BNOMVHZDJIXZAA-UHFFFAOYSA-N 0.000 description 2
- PZYFAYMXLISRGL-UHFFFAOYSA-N 2-methylhexanenitrile Chemical compound CCCCC(C)C#N PZYFAYMXLISRGL-UHFFFAOYSA-N 0.000 description 2
- UFMXUNXYYDTTSW-UHFFFAOYSA-N 3,7-dimethyloct-6-en-1-amine Chemical compound NCCC(C)CCC=C(C)C UFMXUNXYYDTTSW-UHFFFAOYSA-N 0.000 description 2
- ZHJCCVURMXEYJC-UHFFFAOYSA-N 4-(4-octylphenyl)aniline Chemical group C1=CC(CCCCCCCC)=CC=C1C1=CC=C(N)C=C1 ZHJCCVURMXEYJC-UHFFFAOYSA-N 0.000 description 2
- DMVOXQPQNTYEKQ-UHFFFAOYSA-N 4-Aminobiphenyl Chemical group C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 2
- NBGBULBQONOCAX-HNNXBMFYSA-N 4-[(3S)-3,7-dimethyloct-6-enoxy]benzonitrile Chemical compound CC(C)=CCC[C@H](C)CCOC1=CC=C(C#N)C=C1 NBGBULBQONOCAX-HNNXBMFYSA-N 0.000 description 2
- DBTDKIHUSDAJJJ-AWEZNQCLSA-N 4-[(3S)-3,7-dimethyloct-6-enyl]aniline Chemical compound CC(C)=CCC[C@H](C)CCC1=CC=C(N)C=C1 DBTDKIHUSDAJJJ-AWEZNQCLSA-N 0.000 description 2
- JOEAZYGVZBSITL-SFHVURJKSA-N 4-[4-[(3S)-3,7-dimethyloct-6-enyl]phenyl]aniline Chemical group C1=CC(CC[C@H](CCC=C(C)C)C)=CC=C1C1=CC=C(N)C=C1 JOEAZYGVZBSITL-SFHVURJKSA-N 0.000 description 2
- VLVCDUSVTXIWGW-UHFFFAOYSA-N 4-iodoaniline Chemical compound NC1=CC=C(I)C=C1 VLVCDUSVTXIWGW-UHFFFAOYSA-N 0.000 description 2
- QPKCDMXLSDFCQD-UHFFFAOYSA-N 8-bromo-2,6-dimethyloct-2-ene Chemical compound BrCCC(C)CCC=C(C)C QPKCDMXLSDFCQD-UHFFFAOYSA-N 0.000 description 2
- XKBGEWXEAPTVCK-UHFFFAOYSA-M Aliquat 336 Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N Benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N Bis(trimethylsilyl)amine Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N Chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N Methyl acetate Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- WLLGXSLBOPFWQV-UHFFFAOYSA-N N-Octyl bicycloheptene dicarboximide Chemical compound C1=CC2CC1C1C2C(=O)N(CC(CC)CCCC)C1=O WLLGXSLBOPFWQV-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N Sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- AKHNMLFCWUSKQB-UHFFFAOYSA-L Sodium thiosulphate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
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-
2007
- 2007-11-19 EP EP07862121.6A patent/EP2086974B1/en not_active Not-in-force
- 2007-11-19 JP JP2009537237A patent/JP5380296B2/ja not_active Expired - Fee Related
- 2007-11-19 US US11/986,019 patent/US7902363B2/en active Active
- 2007-11-19 WO PCT/US2007/024189 patent/WO2008063609A2/en active Application Filing
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