IL41837A - Process for the manufacture of fluorinated-side-chain derivatives of benzonitrile and certain new such compounds - Google Patents
Process for the manufacture of fluorinated-side-chain derivatives of benzonitrile and certain new such compoundsInfo
- Publication number
- IL41837A IL41837A IL7341837A IL4183773A IL41837A IL 41837 A IL41837 A IL 41837A IL 7341837 A IL7341837 A IL 7341837A IL 4183773 A IL4183773 A IL 4183773A IL 41837 A IL41837 A IL 41837A
- Authority
- IL
- Israel
- Prior art keywords
- benzonitrile
- fluorinated
- compounds
- side chain
- reaction
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 19
- 150000001875 compounds Chemical class 0.000 title claims description 17
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 150000008359 benzonitriles Chemical class 0.000 title description 8
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 40
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 34
- 238000006243 chemical reaction Methods 0.000 claims description 16
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 7
- 229910052787 antimony Inorganic materials 0.000 claims description 6
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 4
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 claims description 3
- 229910001515 alkali metal fluoride Inorganic materials 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 239000013543 active substance Substances 0.000 description 12
- 239000000460 chlorine Substances 0.000 description 10
- 238000004821 distillation Methods 0.000 description 10
- 229910052801 chlorine Inorganic materials 0.000 description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 241000196324 Embryophyta Species 0.000 description 7
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 150000002825 nitriles Chemical class 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 6
- 238000003682 fluorination reaction Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 230000009183 running Effects 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- PGODGMISOACXQO-UHFFFAOYSA-N 2,4-bis(trichloromethyl)benzonitrile Chemical compound ClC(Cl)(Cl)C1=CC=C(C#N)C(C(Cl)(Cl)Cl)=C1 PGODGMISOACXQO-UHFFFAOYSA-N 0.000 description 4
- MMKQAKSXMUSZAY-UHFFFAOYSA-N 2-chloro-5-(trichloromethyl)benzonitrile Chemical compound ClC1=CC=C(C(Cl)(Cl)Cl)C=C1C#N MMKQAKSXMUSZAY-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- KHBCTNHFESKSDC-UHFFFAOYSA-N 4-(trichloromethyl)benzonitrile Chemical compound ClC(Cl)(Cl)C1=CC=C(C#N)C=C1 KHBCTNHFESKSDC-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 241001617088 Thanatephorus sasakii Species 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 238000004508 fractional distillation Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 235000003270 potassium fluoride Nutrition 0.000 description 3
- 239000011698 potassium fluoride Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- -1 trichloromethyl benzonitriles Chemical class 0.000 description 3
- 238000013022 venting Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IGIZEQAEUZAKFJ-UHFFFAOYSA-N 1,3,5-tris[2-(dichloromethyl)-4-fluorophenyl]-2,4-dihydrotriazine Chemical compound FC1=CC(=C(C=C1)N1NN(CC(=C1)C1=C(C=C(C=C1)F)C(Cl)Cl)C1=C(C=C(C=C1)F)C(Cl)Cl)C(Cl)Cl IGIZEQAEUZAKFJ-UHFFFAOYSA-N 0.000 description 2
- IKBXGYXPEGFKLJ-UHFFFAOYSA-N 2,4-bis[chloro(difluoro)methyl]benzonitrile Chemical compound FC(C1=C(C#N)C=CC(=C1)C(Cl)(F)F)(Cl)F IKBXGYXPEGFKLJ-UHFFFAOYSA-N 0.000 description 2
- OZOQTENKIVKILK-UHFFFAOYSA-N 2,5-dimethylbenzonitrile Chemical compound CC1=CC=C(C)C(C#N)=C1 OZOQTENKIVKILK-UHFFFAOYSA-N 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- SOZGHDCEWOLLHV-UHFFFAOYSA-N 2-(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)C1=CC=CC=C1C#N SOZGHDCEWOLLHV-UHFFFAOYSA-N 0.000 description 2
- DRNJIKRLQJRKMM-UHFFFAOYSA-N 4-(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)C1=CC=C(C#N)C=C1 DRNJIKRLQJRKMM-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- GUNJVIDCYZYFGV-UHFFFAOYSA-K antimony trifluoride Chemical compound F[Sb](F)F GUNJVIDCYZYFGV-UHFFFAOYSA-K 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- 239000011241 protective layer Substances 0.000 description 2
- 230000000630 rising effect Effects 0.000 description 2
- 238000010517 secondary reaction Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- GRUHREVRSOOQJG-UHFFFAOYSA-N 2,4-dichlorobenzonitrile Chemical compound ClC1=CC=C(C#N)C(Cl)=C1 GRUHREVRSOOQJG-UHFFFAOYSA-N 0.000 description 1
- QLZDTHTXOUOSCV-UHFFFAOYSA-N 2,4-dimethylbenzonitrile Chemical compound CC1=CC=C(C#N)C(C)=C1 QLZDTHTXOUOSCV-UHFFFAOYSA-N 0.000 description 1
- IRSLAKBEDALSPF-UHFFFAOYSA-N 2,5-bis(trichloromethyl)benzonitrile Chemical compound ClC(Cl)(Cl)C1=CC=C(C(Cl)(Cl)Cl)C(C#N)=C1 IRSLAKBEDALSPF-UHFFFAOYSA-N 0.000 description 1
- ANWBHDYEEOSTSE-UHFFFAOYSA-N 2,6-bis(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)C1=CC=CC(C(F)(F)F)=C1C#N ANWBHDYEEOSTSE-UHFFFAOYSA-N 0.000 description 1
- SYWSBUNPAXEXJP-UHFFFAOYSA-N 2-(dichloromethyl)-4-fluorobenzonitrile Chemical compound FC1=CC(=C(C#N)C=C1)C(Cl)Cl SYWSBUNPAXEXJP-UHFFFAOYSA-N 0.000 description 1
- GBKJYWAWSNXSIQ-UHFFFAOYSA-N 2-(trichloromethyl)benzonitrile Chemical compound ClC(Cl)(Cl)C1=CC=CC=C1C#N GBKJYWAWSNXSIQ-UHFFFAOYSA-N 0.000 description 1
- VBLXCTYLWZJBKA-UHFFFAOYSA-N 2-(trifluoromethyl)aniline Chemical class NC1=CC=CC=C1C(F)(F)F VBLXCTYLWZJBKA-UHFFFAOYSA-N 0.000 description 1
- MVKIIURPUQNNNL-UHFFFAOYSA-N 2-chloro-4-(trichloromethyl)benzonitrile Chemical compound ClC1=CC(C(Cl)(Cl)Cl)=CC=C1C#N MVKIIURPUQNNNL-UHFFFAOYSA-N 0.000 description 1
- LCISFYAQKHOWBP-UHFFFAOYSA-N 2-chloro-5-(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)C1=CC=C(Cl)C(C#N)=C1 LCISFYAQKHOWBP-UHFFFAOYSA-N 0.000 description 1
- LYVYBPBWMKDRGV-UHFFFAOYSA-N 3-(trichloromethyl)benzonitrile Chemical compound ClC(Cl)(Cl)C1=CC=CC(C#N)=C1 LYVYBPBWMKDRGV-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- FDKBUIPAGVFRQZ-UHFFFAOYSA-N FC=1C(=C(C#N)C=CC1)C(Cl)Cl Chemical compound FC=1C(=C(C#N)C=CC1)C(Cl)Cl FDKBUIPAGVFRQZ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 206010053759 Growth retardation Diseases 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
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 241000220261 Sinapis Species 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- HXELGNKCCDGMMN-UHFFFAOYSA-N [F].[Cl] Chemical group [F].[Cl] HXELGNKCCDGMMN-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Inorganic materials [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
- C07C17/202—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction
- C07C17/208—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction the other compound being MX
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/50—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2214061A DE2214061A1 (de) | 1972-03-23 | 1972-03-23 | Seitenkettenfluorierte benzonitrile |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL41837A0 IL41837A0 (en) | 1973-05-31 |
| IL41837A true IL41837A (en) | 1977-06-30 |
Family
ID=5839853
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL7341837A IL41837A (en) | 1972-03-23 | 1973-03-20 | Process for the manufacture of fluorinated-side-chain derivatives of benzonitrile and certain new such compounds |
Country Status (10)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0073372B1 (en) * | 1981-08-31 | 1984-08-01 | Ishihara Sangyo Kaisha, Ltd. | Process for producing 2,6-difluorobenzonitrile |
| JPS63145262A (ja) * | 1986-12-08 | 1988-06-17 | Central Glass Co Ltd | トリフルオロメチルベンゾニトリルの製造方法 |
| DE3836159A1 (de) * | 1988-10-24 | 1990-04-26 | Bayer Ag | Neue fluor enthaltende und an der ch(pfeil abwaerts)3(pfeil abwaerts)-gruppe gegebenenfalls halogenierte acetophenone und deren herstellung aus neuen fluor enthaltenden benzonitrilen |
| JPH047858U (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1990-05-10 | 1992-01-24 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2853524A (en) * | 1958-09-23 | ccifz | ||
| US3012058A (en) * | 1958-05-15 | 1961-12-05 | Pennsalt Chemicals Corp | Nitrile compounds |
| US3489784A (en) * | 1967-03-30 | 1970-01-13 | Hoffmann La Roche | (chlorinated alpha,alpha,alpha - trifluoro-m-tolyl)acetonitriles,acetamides and acetic acids |
-
1972
- 1972-03-23 DE DE2214061A patent/DE2214061A1/de active Pending
-
1973
- 1973-03-05 US US338007A patent/US3916007A/en not_active Expired - Lifetime
- 1973-03-20 NL NL7303885A patent/NL7303885A/xx unknown
- 1973-03-20 JP JP48031561A patent/JPS495943A/ja active Pending
- 1973-03-20 IL IL7341837A patent/IL41837A/en unknown
- 1973-03-21 IT IT21935/73A patent/IT981534B/it active
- 1973-03-21 GB GB1352973A patent/GB1401559A/en not_active Expired
- 1973-03-22 BE BE129114A patent/BE797160A/xx unknown
- 1973-03-23 FR FR7310534A patent/FR2177093B1/fr not_active Expired
- 1973-03-26 CH CH435373A patent/CH576430A5/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2177093B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-03-03 |
| NL7303885A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-09-25 |
| US3916007A (en) | 1975-10-28 |
| BE797160A (fr) | 1973-09-24 |
| GB1401559A (en) | 1975-07-16 |
| CH576430A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-06-15 |
| IT981534B (it) | 1974-10-10 |
| DE2214061A1 (de) | 1973-09-27 |
| FR2177093A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-11-02 |
| IL41837A0 (en) | 1973-05-31 |
| JPS495943A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-01-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN113754648B (zh) | 一种砜吡草唑及其中间体的制备方法 | |
| US3084192A (en) | Alpha-halo-formamidines | |
| Kleinschmidt et al. | Rearrangement of allyl groups in dyad systems. amine oxides | |
| US3957852A (en) | Diphenyl ether compounds | |
| Rousseau et al. | Structure and Ultraviolet Absorption Spectra of Indazole, 3-Substituted Indazole and Some of Their Derivatives1 | |
| US4134917A (en) | Method for the denitrosation of organic nitrosamines | |
| IL41837A (en) | Process for the manufacture of fluorinated-side-chain derivatives of benzonitrile and certain new such compounds | |
| Bergmann et al. | A New Method for the Preparation of Aromatic Fluorine Compounds | |
| US2826611A (en) | Process for making ar-dinitro-phenylureas | |
| CS235967B2 (en) | Method of 1,1-dihalogen-1,2,2,2-tetrafluorethans production | |
| Duffey et al. | Wallach transformation rates of substituted azoxybenzenes | |
| Rappoport et al. | Nucleophilic attacks on carbon-carbon double bonds. Part 39. Nucleophile and nucleofuge effects, catalysis and stereochemistry in vinylic substitution of electrophilic nitro olefins | |
| EP0031218B1 (en) | A 2-amino-trifluoromethyl-halogenopyridine compound and a process for producing the same | |
| US4996377A (en) | Preparation of aliphatically substituted fluorobenzenes | |
| US2945865A (en) | Phthalides | |
| US3355454A (en) | Nu-trifluoromethylamines and process for their production | |
| JPS5989673A (ja) | 植物病原性かび殺滅剤および製造方法 | |
| Bissell | Fluorine-Containing Nitrogen Compounds. V. Difluoronitroacetamidines and Difluoronitromethyl-1, 2, 4-triazoles1, 2 | |
| US3829460A (en) | Preparation of trifluoromethyl aromatic isocyanates | |
| US3249606A (en) | Process of preparing beta-amino-arylethylketone picrates | |
| JPS58206576A (ja) | シス−２，６−ジメチルモルホリンの製法 | |
| US4145553A (en) | Manufacture of 4-nitroimidazoles | |
| US2770651A (en) | Preparation of 2-methyl-4 chlorophenoxy-acetic acid | |
| US2727035A (en) | 3-substituted-2-thiono-4-keto-thiazanes | |
| NO117364B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |