JPS6023358A - ２，４，６−トリフルオロベンゾニトリル - Google Patents
２，４，６−トリフルオロベンゾニトリルInfo
- Publication number
- JPS6023358A JPS6023358A JP13174183A JP13174183A JPS6023358A JP S6023358 A JPS6023358 A JP S6023358A JP 13174183 A JP13174183 A JP 13174183A JP 13174183 A JP13174183 A JP 13174183A JP S6023358 A JPS6023358 A JP S6023358A
- Authority
- JP
- Japan
- Prior art keywords
- trifluorobenzonitrile
- reaction
- trichlorobenzonitrile
- chloride
- chloro
- 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
- HTKFGTCCOJIUIK-UHFFFAOYSA-N 2,4,6-trifluorobenzonitrile Chemical compound FC1=CC(F)=C(C#N)C(F)=C1 HTKFGTCCOJIUIK-UHFFFAOYSA-N 0.000 title abstract 3
- OHDYZVVLNPXKDX-UHFFFAOYSA-N 2,3-dichlorobenzonitrile Chemical compound ClC1=CC=CC(C#N)=C1Cl OHDYZVVLNPXKDX-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract description 6
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 abstract description 5
- 241000238631 Hexapoda Species 0.000 abstract description 3
- 239000003905 agrochemical Substances 0.000 abstract description 3
- 239000003814 drug Substances 0.000 abstract description 3
- 229940079593 drug Drugs 0.000 abstract description 3
- 239000000975 dye Substances 0.000 abstract description 3
- 239000002798 polar solvent Substances 0.000 abstract description 3
- 241000607479 Yersinia pestis Species 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- 235000003270 potassium fluoride Nutrition 0.000 abstract description 2
- 239000011698 potassium fluoride Substances 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- PGODHCIOIPODFE-UHFFFAOYSA-N 2,4,6-trichlorobenzonitrile Chemical compound ClC1=CC(Cl)=C(C#N)C(Cl)=C1 PGODHCIOIPODFE-UHFFFAOYSA-N 0.000 abstract 2
- GWCREUPCCPPMNC-UHFFFAOYSA-N n-[[3,5-dichloro-4-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxyphenyl]carbamoyl]-2,4,6-trifluorobenzamide Chemical compound FC1=CC(F)=CC(F)=C1C(=O)NC(=O)NC(C=C1Cl)=CC(Cl)=C1OC1=NC=C(C(F)(F)F)C=C1Cl GWCREUPCCPPMNC-UHFFFAOYSA-N 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- HVKCZUVMQPUWSX-UHFFFAOYSA-N 1-bromo-2,3-dichlorobenzene Chemical compound ClC1=CC=CC(Br)=C1Cl HVKCZUVMQPUWSX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000003682 fluorination reaction Methods 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- GDHXJNRAJRCGMX-UHFFFAOYSA-N 2-fluorobenzonitrile Chemical compound FC1=CC=CC=C1C#N GDHXJNRAJRCGMX-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000007333 cyanation reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13174183A JPS6023358A (ja) | 1983-07-19 | 1983-07-19 | ２，４，６−トリフルオロベンゾニトリル |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13174183A JPS6023358A (ja) | 1983-07-19 | 1983-07-19 | ２，４，６−トリフルオロベンゾニトリル |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6023358A true JPS6023358A (ja) | 1985-02-05 |
| JPH037662B2 JPH037662B2 (enrdf_load_stackoverflow) | 1991-02-04 |
Family
ID=15065103
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13174183A Granted JPS6023358A (ja) | 1983-07-19 | 1983-07-19 | ２，４，６−トリフルオロベンゾニトリル |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6023358A (enrdf_load_stackoverflow) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5021605A (en) * | 1987-09-14 | 1991-06-04 | Sds Biotech K.K. | Trifluorobenzene compounds |
| US5200548A (en) * | 1984-06-04 | 1993-04-06 | Bayer Aktiengesellschaft | 2,4,5-Trihalogeno- and 2,3,4,5-tetrahalogenobenzene derivatives |
| US5530158A (en) * | 1984-06-04 | 1996-06-25 | Bayer Aktiengesellschaft | 2,4,5-trihalogeno- and 2,3,4,5-tetrahalogenobenzene derivatives |
| CN113929595A (zh) * | 2021-11-12 | 2022-01-14 | 江苏新河农用化工有限公司 | 一种2,6-二氟苯腈的制备方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS604159A (ja) * | 1983-06-23 | 1985-01-10 | Ishihara Sangyo Kaisha Ltd | フルオロベンゾニトリル系化合物の製造方法 |
-
1983
- 1983-07-19 JP JP13174183A patent/JPS6023358A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS604159A (ja) * | 1983-06-23 | 1985-01-10 | Ishihara Sangyo Kaisha Ltd | フルオロベンゾニトリル系化合物の製造方法 |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5200548A (en) * | 1984-06-04 | 1993-04-06 | Bayer Aktiengesellschaft | 2,4,5-Trihalogeno- and 2,3,4,5-tetrahalogenobenzene derivatives |
| US5362909A (en) * | 1984-06-04 | 1994-11-08 | Bayer Aktiengesellschaft | Process for the preparation of 3-chloro-2,4,5-trifluorobenzoyl chloride, 2,4,5-trifuluorobenzoyl fluoride, and 2,3,4,5-tetrahalogenobenzene derivatives |
| US5530158A (en) * | 1984-06-04 | 1996-06-25 | Bayer Aktiengesellschaft | 2,4,5-trihalogeno- and 2,3,4,5-tetrahalogenobenzene derivatives |
| US5565614A (en) * | 1984-06-04 | 1996-10-15 | Bayer Aktiengesellschaft | 2,4,5-trihalogeno-and 2,3,4,5-tetrahalogenobenzene derivatives |
| US5021605A (en) * | 1987-09-14 | 1991-06-04 | Sds Biotech K.K. | Trifluorobenzene compounds |
| CN113929595A (zh) * | 2021-11-12 | 2022-01-14 | 江苏新河农用化工有限公司 | 一种2,6-二氟苯腈的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH037662B2 (enrdf_load_stackoverflow) | 1991-02-04 |
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