对三氟甲基苯胺(p-trifluromethylaniline,缩写为PTFMA,CAS 登录号为455-14-1)是一种重要的化工原料,在农药和医药方面的应用非常广泛。通过氯化反应可以得到2,6-二氯对氨基三氟甲苯,作为重要中间体用于合成高效低毒杀虫剂如氟虫腈(锐劲特)、氟胺氰菊酯、氟幼脲等,以及除草剂乙丁氟灵和乙丁烯氟灵。在医药工业中,它可用于合成新型免疫抑制剂药品来氟米特。
随着绿色化工技术和新型药物研究的不断深入,新的用途持续被开发出来,对三氟甲基苯胺已经成为重要的有发展前景的化工产品。
应用2,6-二氯-4-三氟甲基苯胺是重要的农药合成中间体,主要用来合成含氟有机农药。具体制备方法如下:在3L反应釜中加入200g对三氟甲基苯胺和480g二氯乙烷,并控制温度至10℃。于3小时内搅拌下滴加503g磺酰氯与190g二氯乙烷混合液,滴加完毕后在50℃继续反应2小时。反应完成后降温、水洗并用饱和碳酸钠水溶液洗涤以除去无机盐。有机相浓缩脱除溶剂后精馏得到2,6-二氯-4-三氟甲基苯胺144g。
化学性质本品为无色液体,熔点38℃,沸点在8kPa(83℃)/1.6kPa下分别为117.5℃和83℃。折射率20℃时为1.4840,相对密度为1.2830。该物质难溶于水,易溶于有机溶剂。
用途对三氟甲基苯胺是重要的医药、农药中间体,可用来制备氟胺氰菊酯、氟虫腈、氟幼脲等农药。
生产方法其生产方法主要有以下几种:
对硝基甲苯为原料法:以对硝基甲苯为原料与溴进行溴化反应生成对二溴甲基硝基苯,再用次溴酸钠进行溴化生成对三溴甲基硝基苯,随后使用三氟化锑进行氟化,并通过二氯化锡还原得到对三氟甲基苯胺。这是一种经典方法,原料易得,但需要大量使用溴且工艺复杂,会产生较多的三废。
对氯三氟甲苯为原料法:在150~240℃高压和高温条件下,对氯三氟甲苯与氨反应生成对三氟甲基苯胺。尽管对氯三氟甲苯是工业化商品,但氨解条件苛刻,工业化具有一定难度。
对三氯甲基苯异氰酸酯为原料法:通过对三氯甲基苯异氰酸酯与氟化氢反应生成对三氟甲基苯胺的氢氟酸盐,并与碱反应制得。此方法是近年来国外开发的技术,而对三氯甲基苯异氰酸酯可以通过对甲基苯胺通光气生成。
以对氯三氟甲苯为原料直接合成法:在高压条件下,使用对氯三氟甲苯和氨进行反应,制得2,6-二氯-4-三氟甲基苯胺。
中文名称 | 英文名称 | CAS号 | 化学式 | 分子量 |
---|---|---|---|---|
—— | N-(4-(trifluoromethyl)phenyl)hydroxylamine | 102512-07-2 | C7H6F3NO | 177.126 |
4-(三氟甲基)苯肼 | 4-(trifluoromethyl)phenylhydrazine | 368-90-1 | C7H7F3N2 | 176.141 |
—— | 1-nitroso-4-(trifluoromethyl)benzene | 34913-26-3 | C7H4F3NO | 175.11 |
N,N-二甲基-4-(三氟甲基)苯胺 | N,N-dimethyl-4-(trifluoromethyl)aniline | 329-17-9 | C9H10F3N | 189.18 |
—— | N-(4-(trifluoromethyl)phenyl)formamide | 74702-40-2 | C8H6F3NO | 189.137 |
1-叠氮基-4-(三氟甲基)苯 | 1-azido-4-(trifluoromethyl)benzene | 5586-13-0 | C7H4F3N3 | 187.124 |
4-(三氟甲基)异硫氰酸苯酯 | 4-(trifluoromethyl)phenyl isothiocyanate | 1645-65-4 | C8H4F3NS | 203.188 |
—— | (E)-1-phenyl-2-(4-(trifluoromethyl)phenyl)diazene | 98217-68-6 | C13H9F3N2 | 250.223 |
重氮基烯,苯基[4-(三氟甲基)苯基]- | 1-phenyl-2-(4-(trifluoromethyl)phenyl)diazene | 1815-14-1 | C13H9F3N2 | 250.223 |
4-硝基三氟甲苯 | p-nitrobenzotrifluoride | 402-54-0 | C7H4F3NO2 | 191.109 |
N1-[4-(三氟甲基0苯基]乙酰氨 | 4-(trifluromethyl)acetanilide | 349-97-3 | C9H8F3NO | 203.164 |
对氯三氟甲苯 | 4-chlorobenzotrifluoride | 98-56-6 | C7H4ClF3 | 180.557 |
对溴三氟甲苯 | p-trifluoromethylphenyl bromide | 402-43-7 | C7H4BrF3 | 225.008 |
—— | 1-phenyl-3-(4-(trifluoromethyl)phenyl)thiourea | —— | C14H11F3N2S | 296.316 |
—— | methyl (4-(trifluoromethyl)phenyl)carbamate | 23794-77-6 | C9H8F3NO2 | 219.163 |
1,3-双[4-(三氟甲基)苯基]尿素 | 1,3-bis(4-(trifluoromethyl)phenyl)urea | 1960-88-9 | C15H10F6N2O | 348.248 |
4-碘三氟甲苯 | 4-Iodobenzotrifluoride | 455-13-0 | C7H4F3I | 272.008 |
对三氟甲基苯酚 | 4-Trifluoromethylphenol | 402-45-9 | C7H5F3O | 162.111 |
—— | 1,3-bis(4-(trifluoromethyl)phenyl)triazene | 7639-95-4 | C14H9F6N3 | 333.236 |
中文名称 | 英文名称 | CAS号 | 化学式 | 分子量 |
---|---|---|---|---|
4-三氟甲基-N-甲基苯胺 | N-methyl-4-(trifluoromethyl)aniline | 22864-65-9 | C8H8F3N | 175.153 |
4-(三氟甲基)苯肼 | 4-(trifluoromethyl)phenylhydrazine | 368-90-1 | C7H7F3N2 | 176.141 |
—— | 1-nitroso-4-(trifluoromethyl)benzene | 34913-26-3 | C7H4F3NO | 175.11 |
—— | p-trifluoromethyl(sulfinylaniline) | 74653-66-0 | C7H4F3NOS | 207.176 |
N,N-二甲基-4-(三氟甲基)苯胺 | N,N-dimethyl-4-(trifluoromethyl)aniline | 329-17-9 | C9H10F3N | 189.18 |
—— | N-(4-(trifluoromethyl)phenyl)formamide | 74702-40-2 | C8H6F3NO | 189.137 |
4-三氟甲基苯基异氰酸酯 | p-trifluoromethyl-phenylisocyanate | 1548-13-6 | C8H4F3NO | 187.121 |
—— | 4-trifluoromethylphenylthioformamide | —— | C8H6F3NS | 205.204 |
N-乙基-4-(三氟甲基)苯胺 | N-ethyl-4-(trifluoromethyl)aniline | 820209-45-8 | C9H10F3N | 189.18 |
—— | phenyl(4-trifluoromethylphenyl)amine | 53451-87-9 | C13H10F3N | 237.224 |
4-(三氟甲基)-N-[4-(三氟甲基)苯基]苯胺 | bis(4-(trifluoromethyl)phenyl)amine | 7639-71-6 | C14H9F6N | 305.223 |
—— | 4-methyl-N-(4-(trifluoromethyl)phenyl)aniline | 88429-26-9 | C14H12F3N | 251.251 |
4-(三氟甲基)异硫氰酸苯酯 | 4-(trifluoromethyl)phenyl isothiocyanate | 1645-65-4 | C8H4F3NS | 203.188 |
1-叠氮基-4-(三氟甲基)苯 | 1-azido-4-(trifluoromethyl)benzene | 5586-13-0 | C7H4F3N3 | 187.124 |
三氟甲苯 | α,α,α-trifluorotoluene | 98-08-8 | C7H5F3 | 146.112 |
间氨基三氟甲苯 | 3-trifluoromethylaniline | 98-16-8 | C7H6F3N | 161.127 |
—— | 1-phenyl-2-(4-(trifluoromethyl)phenyl)hydrazine | 1815-08-3 | C13H11F3N2 | 252.239 |
—— | N-[4-(trifluoromethyl)phenyl]-S,S-dimethylsulfilimine | 362640-55-9 | C9H10F3NS | 221.246 |
—— | N1-(4-(trifluoromethyl)phenyl)ethane-1,2-diamine | 933692-26-3 | C9H11F3N2 | 204.195 |
—— | (E)-1-phenyl-2-(4-(trifluoromethyl)phenyl)diazene | 98217-68-6 | C13H9F3N2 | 250.223 |
重氮基烯,苯基[4-(三氟甲基)苯基]- | 1-phenyl-2-(4-(trifluoromethyl)phenyl)diazene | 1815-14-1 | C13H9F3N2 | 250.223 |
N-[4-(三氟甲基)苯基]胍 | 1-(4-(trifluoromethyl)phenyl)guanidine | 130066-24-9 | C8H8F3N3 | 203.167 |
—— | N-isopropyl-4-(trifluoromethyl)aniline | 1020920-65-3 | C10H12F3N | 203.207 |
[[4-(三氟甲基)苯基]氨基]-乙腈 | 2-((4-(trifluoromethyl) phenyl) amino) acetonitrile | 672333-10-7 | C9H7F3N2 | 200.163 |
4-(三氟甲基)-N-炔丙基苯胺 | 4-(trifluoromethyl)-N-propargylaniline | 233272-89-4 | C10H8F3N | 199.175 |
—— | N1-(4-(trifluoromethyl)phenyl)benzene-1,4-diamine | 1152560-50-3 | C13H11F3N2 | 252.239 |
—— | N-propylidene-4-trifluoromethylphenylamine | —— | C10H10F3N | 201.191 |
N-丙基-4-(三氟甲基)苯胺 | N-propyl-4-(trifluoromethyl)aniline | 190843-72-2 | C10H12F3N | 203.207 |
—— | tert-butyl(4-trifluoromethylphenyl)amine | 1361233-11-5 | C11H14F3N | 217.234 |
4-甲基三氟甲苯 | 4-methylbenzotrifluoride | 6140-17-6 | C8H7F3 | 160.139 |
4-硝基三氟甲苯 | p-nitrobenzotrifluoride | 402-54-0 | C7H4F3NO2 | 191.109 |
—— | N-butyl-4-(trifluoromethyl)aniline | 830325-03-6 | C11H14F3N | 217.234 |
—— | N,N-dimethyl-N'-[4-(trifluoromethyl)phenyl]methanimidamide | 29366-21-0 | C10H11F3N2 | 216.206 |
对二三氟甲苯 | 1,4-bis(trifluoromethyl)benzene | 433-19-2 | C8H4F6 | 214.11 |
—— | 1-(difluoromethyl)-4-(trifluoromethyl)benzene | 2251-82-3 | C8H5F5 | 196.12 |
—— | 4-(4-trifluoromethylphenylazo)aniline | 1961-53-1 | C13H10F3N3 | 265.238 |
—— | 4-[[4-(trifluoromethyl)phenyl]diazenyl]aniline | 1961-53-1 | C13H10F3N3 | 265.238 |
4-三氟甲基苯硫脲 | 1-(4-(trifluoromethyl)phenyl)thiourea | 1736-72-7 | C8H7F3N2S | 220.218 |
—— | N-(2,2,2-trifluoroethyl)-4-(trifluoromethyl)aniline | 1021128-03-9 | C9H7F6N | 243.152 |
—— | 1-(4-(trifluoromethyl)phenyl)urea | —— | C8H7F3N2O | 204.152 |
—— | 4-(trifluoromethyl)phenyl-aminoformyl chloride | —— | C8H5ClF3NO | 223.582 |
—— | 4-(trifluoromethyl)phenylcarbamayl fluoride | 54041-82-6 | C8H5F4NO | 207.127 |
N1-[4-(三氟甲基0苯基]乙酰氨 | 4-(trifluromethyl)acetanilide | 349-97-3 | C9H8F3NO | 203.164 |
—— | N1-(4-(trifluoromethyl)phenyl)benzene-1,3-diamine | —— | C13H11F3N2 | 252.239 |
—— | N,N-diethyl-4-(trifluoromethyl)aniline | 106877-27-4 | C11H14F3N | 217.234 |
—— | N-hexyl-4-(trifluoromethyl)aniline | —— | C13H18F3N | 245.288 |
—— | N-[4-(trifluoromethyl)phenyl]nitramide | 69732-95-2 | C7H5F3N2O2 | 206.124 |
—— | N'-(p-trifluoromethylphenyl)acetamidine | 1002107-28-9 | C9H9F3N2 | 202.179 |
—— | 2-((4-(trifluoromethyl)phenyl)amino)acetic acid | —— | C9H8F3NO2 | 219.163 |
3-氯-4-氨基三氟甲苯 | 2-chloro-4-(trifluoromethyl)aniline | 39885-50-2 | C7H5ClF3N | 195.572 |
—— | 2-amino-5-(trifluoromethyl)benzenethiol | 86691-07-8 | C7H6F3NS | 193.193 |
—— | N-benzylidene-4-(trifluoromethyl)aniline | 351-98-4 | C14H10F3N | 249.235 |
2-氟-4-(三氟甲基)苯胺 | 2-fluoro-4-(trifluoromethyl)aniline | 69409-98-9 | C7H5F4N | 179.117 |
—— | N-benzyl-4-(trifluoromethyl)aniline | 405-81-2 | C14H12F3N | 251.251 |
4-氨基-3-溴三氟甲苯 | 4-amino-3-bromobenzotrifluoride | 57946-63-1 | C7H5BrF3N | 240.023 |
4-氨基-3-碘三氟甲苯 | 2-iodo-4-(trifluoromethyl)aniline | 163444-17-5 | C7H5F3IN | 287.023 |
对氯三氟甲苯 | 4-chlorobenzotrifluoride | 98-56-6 | C7H4ClF3 | 180.557 |
—— | 4-(4'-trifluoromethylphenylazo)phenol | 4316-21-6 | C13H9F3N2O | 266.222 |
—— | (E)-4-((4-(trifluoromethyl)phenyl)diazenyl)phenol | 4316-21-6 | C13H9F3N2O | 266.222 |
对溴三氟甲苯 | p-trifluoromethylphenyl bromide | 402-43-7 | C7H4BrF3 | 225.008 |
4-(三氟甲基)苯硫酚 | 4-trifluoromethylbenzenethiol | 825-83-2 | C7H5F3S | 178.178 |
2-{2-[4-(三氟甲基)苯基]肼基}丙二腈 | 2-[4-(trifluoromethyl)phenylazo]malononitrile | 7089-17-0 | C10H5F3N4 | 238.172 |
—— | 2-methyl-2-((4-(trifluoromethyl)phenyl)amino)propanenitrile | 915086-62-3 | C11H11F3N2 | 228.217 |
2,4-双(三氟甲基)苯胺 | 2,4-bis(trifluoromethyl)aniline | 367-71-5 | C8H5F6N | 229.125 |
—— | 1-phenyl-1-(4-(trifluoromethyl)phenyl)hydrazine | —— | C13H11F3N2 | 252.239 |
—— | methyl (4-(trifluoromethyl)phenyl)carbamate | 23794-77-6 | C9H8F3NO2 | 219.163 |
1,3-双[4-(三氟甲基)苯基]尿素 | 1,3-bis(4-(trifluoromethyl)phenyl)urea | 1960-88-9 | C15H10F6N2O | 348.248 |
1,3-双[4-(三氟甲基)苯基]硫脲 | 1,3-bis(4-(trifluoromethyl)phenyl)thiourea | 1744-07-6 | C15H10F6N2S | 364.314 |
—— | N-(p-trifluoromethylphenyl)-N'-phenylurea | 23750-69-8 | C14H11F3N2O | 280.249 |
N-(4-三氟甲基苯基)-1,2-苯二胺 | N1-(4-(trifluoromethyl)phenyl)benzene-1,2-diamine | 1038352-61-2 | C13H11F3N2 | 252.239 |
—— | 1-phenyl-3-(4-(trifluoromethyl)phenyl)thiourea | —— | C14H11F3N2S | 296.316 |
—— | 2-fluoro-4-(trifluoromethyl)-acetanilide | 2339-84-6 | C9H7F4NO | 221.154 |
4-[4-(三氟甲基)苯基]-3-硫代氨基脲 | N-(4-(trifluoromethyl)phenyl)hydrazinecarbothioamide | 206761-90-2 | C8H8F3N3S | 235.233 |
—— | N-(4-(difluoromethyl)phenyl)acetamide | 29848-60-0 | C9H9F2NO | 185.173 |
—— | O-Methyl-N-(4-(trifluoromethyl)phenyl)isourea | —— | C9H9F3N2O | 218.178 |
—— | N-(4-methyl-benzylidene)-4-trifluoromethyl-aniline | 2368-21-0 | C15H12F3N | 263.262 |
—— | N-phenethyl-4-(trifluoromethyl)aniline | 59211-38-0 | C15H14F3N | 265.278 |
—— | 2-amino-N-(4-(trifluoromethyl)phenyl)acetamide | 289654-95-1 | C9H9F3N2O | 218.178 |
4-碘三氟甲苯 | 4-Iodobenzotrifluoride | 455-13-0 | C7H4F3I | 272.008 |
—— | N-(4-(trifluoromethyl)phenyl)methanesulfonamide | 50790-32-4 | C8H8F3NO2S | 239.218 |
—— | N-(4-(trifluoromethyl)phenyl)acrylamide | 25617-42-9 | C10H8F3NO | 215.175 |
—— | N-(4-(trifluoromethyl)phenyl)propynamide | —— | C10H6F3NO | 213.159 |
—— | methyl (4-(trifluoromethyl)phenyl)glycinate | 126689-82-5 | C10H10F3NO2 | 233.19 |
4-氟三氟甲苯 | 4-Fluorobenzotrifluoride | 402-44-8 | C7H4F4 | 164.102 |
2-氯-N-[4-(三氟甲基)苯基]乙酰胺 | 2-chloro-N-(4-trifluomethylphenyl)acetamide | 2707-23-5 | C9H7ClF3NO | 237.609 |
2-溴-4-(三氟甲基)-N-乙酰苯胺 | 2-bromo-N-(4-(trifluoromethyl)phenyl)acetamide | 3823-19-6 | C9H7BrF3NO | 282.06 |
—— | (4-(trifluoromethyl)phenyl)sulfamoyl chloride | 391912-56-4 | C7H5ClF3NO2S | 259.636 |
对三氟甲基苯酚 | 4-Trifluoromethylphenol | 402-45-9 | C7H5F3O | 162.111 |
—— | 1,3-bis(4-(trifluoromethyl)phenyl)triazene | 7639-95-4 | C14H9F6N3 | 333.236 |
2,6-二氯-4-三氟甲基苯胺 | 2,6-dichloro-4-(trifluoromethyl)aniline | 24279-39-8 | C7H4Cl2F3N | 230.017 |
—— | N,N-Bis-(2-hydroxyethyl)-4-trifluormethyl-anilin | 324-28-7 | C11H14F3NO2 | 249.233 |
—— | N-(3-chlorophenyl)-4-trifluoromethylaniline | 1338369-75-7 | C13H9ClF3N | 271.669 |
2-氨基-5-三氟甲基苯腈 | 2-amino-5-(trifluoromethyl)benzonitrile | 6526-08-5 | C8H5F3N2 | 186.136 |
4-氨基-3,5-二溴三氟甲苯 | 2,6-Dibromo-4-(trifluoromethyl)aniline | 72678-19-4 | C7H4Br2F3N | 318.919 |
—— | 2-ethynyl-4-(trifluoromethyl)aniline | 878133-02-9 | C9H6F3N | 185.149 |
—— | 4-methoxy-N-(4-(trifluoromethyl)phenyl)aniline | 53451-88-0 | C14H12F3NO | 267.251 |
—— | 4-(trifluoromethyl)-N-(4-(trifluoromethyl)benzyl)aniline | 79128-87-3 | C15H11F6N | 319.249 |
—— | ethyl 2-((4-(trifluoromethyl)phenyl)amino)acetate | 2445-85-4 | C11H12F3NO2 | 247.217 |
—— | N-cinnamyl-4-(trifluoromethyl)aniline | —— | C16H14F3N | 277.289 |