JP2001522822A5 - - Google Patents
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- Publication number
- JP2001522822A5 JP2001522822A5 JP2000520400A JP2000520400A JP2001522822A5 JP 2001522822 A5 JP2001522822 A5 JP 2001522822A5 JP 2000520400 A JP2000520400 A JP 2000520400A JP 2000520400 A JP2000520400 A JP 2000520400A JP 2001522822 A5 JP2001522822 A5 JP 2001522822A5
- Authority
- JP
- Japan
- Prior art keywords
- bromo
- mixture
- fluoro
- substituted
- nmr
- 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.)
- Pending
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- -1 cyclopropane-1,2-diyl Chemical group 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 5
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 description 4
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- GPPYYGWYUFOWSR-UHFFFAOYSA-N 1,3-dibromo-2-fluorobenzene Chemical compound FC1=C(Br)C=CC=C1Br GPPYYGWYUFOWSR-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000006349 photocyclization reaction Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- HCTIXSQEUKSMHY-UHFFFAOYSA-N 1-bromo-2-fluoro-3-hexoxybenzene Chemical compound CCCCCCOC1=CC=CC(Br)=C1F HCTIXSQEUKSMHY-UHFFFAOYSA-N 0.000 description 2
- CEBKHWWANWSNTI-UHFFFAOYSA-N 2-methylbut-3-yn-2-ol Chemical compound CC(C)(O)C#C CEBKHWWANWSNTI-UHFFFAOYSA-N 0.000 description 2
- MEZFCUMYQXLFOV-UHFFFAOYSA-N 3-bromo-2-fluorophenol Chemical compound OC1=CC=CC(Br)=C1F MEZFCUMYQXLFOV-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- YPTHSYKJDRMAJY-UHFFFAOYSA-N 5-bromo-2-fluorophenol Chemical compound OC1=CC(Br)=CC=C1F YPTHSYKJDRMAJY-UHFFFAOYSA-N 0.000 description 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-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
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- QJPQVXSHYBGQGM-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 QJPQVXSHYBGQGM-UHFFFAOYSA-N 0.000 description 2
- 125000001792 phenanthrenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 0 *c1cccc(Br)c1F Chemical compound *c1cccc(Br)c1F 0.000 description 1
- RDEDUKMGXSSWTC-UHFFFAOYSA-N 1,2,3-trifluoro-4-[2-(2-fluoro-3-hexoxyphenyl)ethenyl]benzene Chemical compound CCCCCCOC1=CC=CC(C=CC=2C(=C(F)C(F)=CC=2)F)=C1F RDEDUKMGXSSWTC-UHFFFAOYSA-N 0.000 description 1
- YIXZHEAHOUUHTJ-UHFFFAOYSA-N 1,2,3-trifluoro-4-[2-(2-fluoro-3-hexoxyphenyl)ethynyl]benzene Chemical compound CCCCCCOC1=CC=CC(C#CC=2C(=C(F)C(F)=CC=2)F)=C1F YIXZHEAHOUUHTJ-UHFFFAOYSA-N 0.000 description 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- MUUAQFJJUGVBGB-UHFFFAOYSA-N 1-bromo-2,3,4-trifluorobenzene Chemical compound FC1=CC=C(Br)C(F)=C1F MUUAQFJJUGVBGB-UHFFFAOYSA-N 0.000 description 1
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 1
- VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical compound CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 description 1
- AWMMLXIXWKCHCE-UHFFFAOYSA-N 1-ethynyl-2-fluoro-3-hexoxybenzene Chemical compound CCCCCCOC1=CC=CC(C#C)=C1F AWMMLXIXWKCHCE-UHFFFAOYSA-N 0.000 description 1
- YLNUVAIYEOLXRN-UHFFFAOYSA-N 1-ethynyl-4-fluoro-2-methoxybenzene Chemical compound COC1=CC(F)=CC=C1C#C YLNUVAIYEOLXRN-UHFFFAOYSA-N 0.000 description 1
- JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical compound CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- SEVMQEIGENUPIE-UHFFFAOYSA-N 4-bromo-1-fluoro-2-methoxybenzene Chemical compound COC1=CC(Br)=CC=C1F SEVMQEIGENUPIE-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- NSUIZCXTAAHYBH-UHFFFAOYSA-N CCCCCCC1=C(C(=CC=C1)C#CC(C)CO)F Chemical compound CCCCCCC1=C(C(=CC=C1)C#CC(C)CO)F NSUIZCXTAAHYBH-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 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
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 229930188620 butyrolactone Natural products 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000004979 cyclopentylene group Chemical group 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 125000005447 octyloxy 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])O* 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical class [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19748819.6 | 1997-11-05 | ||
| DE19748819A DE19748819A1 (de) | 1997-11-05 | 1997-11-05 | Fluorierte Derivate des Phenanthrens und ihre Verwendung in Flüssigkristallmischungen |
| PCT/EP1998/007080 WO1999024385A1 (de) | 1997-11-05 | 1998-11-05 | Fluorierte derivate des phenanthrens und ihre verwendung in flüssigkristallmischungen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2001522822A JP2001522822A (ja) | 2001-11-20 |
| JP2001522822A5 true JP2001522822A5 (enExample) | 2006-01-05 |
Family
ID=7847661
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000520400A Pending JP2001522822A (ja) | 1997-11-05 | 1998-11-05 | フェナントレンのフッ素化誘導体、および液晶混合物におけるそれらの使用 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US6482478B1 (enExample) |
| EP (1) | EP1028935B1 (enExample) |
| JP (1) | JP2001522822A (enExample) |
| DE (2) | DE19748819A1 (enExample) |
| WO (1) | WO1999024385A1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19825488A1 (de) * | 1998-06-08 | 1999-12-09 | Aventis Res & Tech Gmbh & Co | Monostabiles ferroelektrisches Aktivmatrix-Display |
| JP4644888B2 (ja) * | 1999-08-03 | 2011-03-09 | Ｄｉｃ株式会社 | フェナントレン及びフルオレン誘導体 |
| JP4605412B2 (ja) * | 1999-08-27 | 2011-01-05 | Ｄｉｃ株式会社 | フェナントレン及びフルオレン誘導体 |
| DE10002186B4 (de) | 2000-01-19 | 2018-01-18 | Merck Patent Gmbh | Disubstituierte Phenanthrene und ihre Verwendung in Flüssigkristallmischungen |
| DE10123088A1 (de) * | 2000-06-08 | 2001-12-13 | Merck Patent Gmbh | Hydrierte Phenanthrene und ihre Verwendung in Flüssigkristallmischungen |
| JP4826005B2 (ja) * | 2000-09-28 | 2011-11-30 | Ｄｉｃ株式会社 | 液晶性化合物の精製方法 |
| DE10064995B4 (de) * | 2000-12-23 | 2009-09-24 | Merck Patent Gmbh | Flüssigkristallines Medium und seine Verwendung in einer elektrooptischen Anzeige |
| DE10225048B4 (de) * | 2001-06-07 | 2015-03-12 | Merck Patent Gmbh | Fluorierte (Dihydro)phenanthrenderivate und deren Verwendung in flüssigkristallinen Medien |
| US6677479B2 (en) | 2001-11-13 | 2004-01-13 | Clariant Finance Lbvi Limited | Substituted fluoroaromatics, process for preparing them and their use |
| DE102004022728B4 (de) * | 2004-05-07 | 2018-08-23 | Merck Patent Gmbh | Fluorierte Phenanthrene und ihre Verwendung in Flüssigkristallmischungen |
| EP1645610A1 (de) * | 2004-10-11 | 2006-04-12 | Covion Organic Semiconductors GmbH | Phenanthren-Derivate |
| KR101250667B1 (ko) * | 2005-03-24 | 2013-04-03 | 메르크 파텐트 게엠베하 | 액정 매질 |
| DE102005026651A1 (de) | 2005-06-09 | 2006-12-14 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
| TWI507511B (zh) | 2013-11-05 | 2015-11-11 | Ind Tech Res Inst | 負介電異方性液晶化合物、液晶顯示器、與光電裝置 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0032362B1 (en) | 1980-01-10 | 1984-08-22 | Noel A. Clark | Chiral smectic liquid crystal electro-optical device and process of making the same |
| DE3920625A1 (de) | 1989-06-23 | 1991-01-03 | Hoechst Ag | Ferroelektrische fluessigkristallelemente mit hoher spontaner polarisation und geringer helixganghoehe |
| EP0405346B1 (de) | 1989-06-29 | 1995-09-20 | F. Hoffmann-La Roche Ag | Bistabile ferroelektrische Flüssigkristallanzeige |
| DE4222565A1 (de) * | 1992-07-09 | 1994-01-13 | Hoechst Ag | Meta-substituierte Sechsringaromaten zur Verwendung in Flüssigkristallmischungen |
| DE19500768C2 (de) | 1994-01-17 | 2003-11-20 | Aventis Res & Tech Gmbh & Co | Phenanthren-Derivate und ihre Verwendung in flüssigkristallinen Mischungen |
| US5648021A (en) | 1994-01-17 | 1997-07-15 | Hoechst Aktiengesellschaft | Phenanthrene derivatives and their use in liquid-crystalline mixtures |
| DE4432970A1 (de) | 1994-09-16 | 1996-03-21 | Hoechst Ag | Tetracyclische Verbindungen und ihre Verwendung in flüssigkristallinen Mischungen |
| US5596047A (en) * | 1994-11-16 | 1997-01-21 | Cytec Technology Corp. | Water-dispersible and curable waterborne compositions containing 1,3,5-triazine carbamates |
| DE19524230A1 (de) * | 1995-07-04 | 1997-01-09 | Hoechst Ag | Fluorierte Phenanthren-Derivate und ihre Verwendung in flüssigkristallinen Mischungen |
| JPH0931459A (ja) * | 1995-07-17 | 1997-02-04 | Hoechst Ag | 新規な強誘電性液晶組成物 |
| DE19653008A1 (de) * | 1996-12-19 | 1998-06-25 | Hoechst Ag | Fluorierte Phenanthren-Derivate und ihre Verwendung in flüssigkristallinen Mischungen |
| JP4048570B2 (ja) * | 1997-02-25 | 2008-02-20 | チッソ株式会社 | 誘電率異方性値が負の液晶性化合物、この液晶性化合物を含有する液晶組成物、及びこの液晶組成物を用いた液晶表示素子 |
-
1997
- 1997-11-05 DE DE19748819A patent/DE19748819A1/de not_active Ceased
-
1998
- 1998-11-05 US US09/530,665 patent/US6482478B1/en not_active Expired - Lifetime
- 1998-11-05 EP EP98961141A patent/EP1028935B1/de not_active Expired - Lifetime
- 1998-11-05 DE DE59812664T patent/DE59812664D1/de not_active Expired - Lifetime
- 1998-11-05 WO PCT/EP1998/007080 patent/WO1999024385A1/de not_active Ceased
- 1998-11-05 JP JP2000520400A patent/JP2001522822A/ja active Pending
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