热分解会排出有毒的溴化物和氮氧化物烟雾。
中文名称 | 英文名称 | CAS号 | 化学式 | 分子量 |
---|---|---|---|---|
—— | 3-bromodinitrobenzene | 13296-65-6 | C6H3BrN2O4 | 247.005 |
间溴硝基苯 | 3-Bromonitrobenzene | 585-79-5 | C6H4BrNO2 | 202.007 |
1,2-二溴-4-硝基苯 | 3,4-dibromonitrobenzene | 5411-50-7 | C6H3Br2NO2 | 280.903 |
N-(2-溴-4-硝基苯基)乙酰胺 | N-(2-bromo-4-nitrophenyl)acetamide | 57045-86-0 | C8H7BrN2O3 | 259.059 |
2-溴-1-碘-4-硝基苯 | 2-bromo-1-iodo-4-nitrobenzene | 7149-14-6 | C6H3BrINO2 | 327.904 |
—— | N-(2-Bromo-4-nitro-phenyl)-2,2,2-trifluoro-acetamide | —— | C8H4BrF3N2O3 | 313.031 |
4-硝基苯胺 | 4-nitro-aniline | 100-01-6 | C6H6N2O2 | 138.126 |
中文名称 | 英文名称 | CAS号 | 化学式 | 分子量 |
---|---|---|---|---|
—— | 2-bromo-4-nitro-1-nitroso-benzene | 408328-21-2 | C6H3BrN2O3 | 231.005 |
2,6-二溴-4-硝基苯胺 | 2,6-dibromo-4-nitroaniline | 827-94-1 | C6H4Br2N2O2 | 295.918 |
—— | N-(2-Bromo-4-nitrophenyl)formamide | 50668-78-5 | C7H5BrN2O3 | 245.032 |
1,2-二溴-4-硝基苯 | 3,4-dibromonitrobenzene | 5411-50-7 | C6H3Br2NO2 | 280.903 |
N-(2-溴-4-硝基苯基)乙酰胺 | N-(2-bromo-4-nitrophenyl)acetamide | 57045-86-0 | C8H7BrN2O3 | 259.059 |
2-溴-4,6-二硝基苯胺 | 2-bromo-4,6-dinitroaniline | 1817-73-8 | C6H4BrN3O4 | 262.019 |
2-氯-4-硝基-6-溴苯胺 | 2-bromo-6-chloro-4-nitroaniline | 99-29-6 | C6H4BrClN2O2 | 251.467 |
2-溴-1-碘-4-硝基苯 | 2-bromo-1-iodo-4-nitrobenzene | 7149-14-6 | C6H3BrINO2 | 327.904 |
2-(4-溴-苯基)-喹啉-4-羧酸 | N-(4-Nitro-2-bromophenyl)methanesulfonamide | 51765-50-5 | C7H7BrN2O4S | 295.114 |
3-溴-4-氯硝基苯 | 3-bromo-4-chloronitrobenzene | 16588-26-4 | C6H3BrClNO2 | 236.452 |
—— | 1,3-bis(2-bromo-4-nitrophenyl)triazene | —— | C12H7Br2N5O4 | 445.027 |
1-溴-3-碘-5-硝基苯 | 1-bromo-3-iodo-5-nitrobenzene | 861601-15-2 | C6H3BrINO2 | 327.904 |
4-硝基苯胺 | 4-nitro-aniline | 100-01-6 | C6H6N2O2 | 138.126 |
—— | (2-bromo-4-nitrophenyl)-carbamic acid tert-butyl ester | 384793-20-8 | C11H13BrN2O4 | 317.139 |
2-溴-1,4-二氨基苯 | 2-bromo-p-phenylenediamine | 13296-69-0 | C6H7BrN2 | 187.039 |
—— | N-(2-bromo-4-nitrophenyl)adipic acid monoamide | 919490-03-2 | C12H13BrN2O5 | 345.15 |
2-溴-4-硝基苯甲腈 | 2-bromo-4-nitrobenzonitrile | 34662-35-6 | C7H3BrN2O2 | 227.017 |
Halodimethylsulfonium halide 1, which is readily formed in situ from hydrohaloic acid and DMSO, is a good nucleophilic halide. This activated nucleophilic halide rapidly converts aryldiazonium salt prepared in situ by the same hydrohaloic acid and nitrite ion to aryl chlorides, bromides, or iodides in good yield. The combined action of nitrite ion and hydrohaloic acid in DMSO is required for the direct transformation of aromatic amines, which results in the production of aryl halides within 1 h. Substituted compounds with electron-donating or -withdrawing groups or sterically hindered aromatic amines are also smoothly transformed to the corresponding aromatic halides. The only observed by-product is the deaminated arene (usually <7%). The isolated aryldiazonium salts can also be converted to the corresponding aryl halides using 1. The present method offers a facile, one-step procedure for transforming aminoarenes to haloarenes and lacks the environmental pollutants that usually accompany the Sandmeyer reaction using copper halides. Key words: aminoarenes, haloarenes, halodimethylsulfonium halide, halogenation, amination.