N-Methyl-p-cyanotetrafluoroaniline | 28012-05-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-Methyl-p-cyanotetrafluoroaniline
• 英文别名: N-methyl-4-cyanotetrafluoroaniline；2,3,5,6-Tetrafluoro-4-(methylamino)benzonitrile
• CAS: 28012-05-7
• 化学式: C₈H₄F₄N₂
• 分子量: 204.127
• InChiKey: ZXZXJMHDQOGPMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  35.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-Methyl-p-cyanotetrafluoroaniline 在 硝酸 作用下， 反应 5.0h， 以65%的产率得到N-Nitro-N-methyl-p-cyanotetrafluoroaniline
  参考文献：
  名称：

  Polyfluorinated arylnitramines

  摘要：

  N-methyl- and N-butylperfluoroarylamines are transformed by HNO3 into N-nitro-N-methyl- and N-nitro-N-butylperfluoroarylamines. These reactions were used to synthesise N-nitro-N-methylpentafluoroaniline and its p-CF3. -CN, -C6F5 substituted derivatives, N-nitro-N-methylperfluoro-2,4-xylidine, N-nitro-N-methyl-4-aminotetrafluoropyridine N-nitro-N-methyl 5-aminoperfluoroindane, N-nitro-N-methyl-2- aminoheptafluoronaphthalene. 4,4 ' -bis(N-nitro-N- merhylamino)octafluorobiphenyl from 4,4 ' -bis(N-methylamino)octafluorobiphenyl, N-nitro-N-n-butylpentafluoroaniline, N-nitro-N-n-butylperfluoro-p-toluidine, N-nitro-N-n-butyl-4-aminotetrafluoropyridine and N-nitro-bis( perfluoro-p-tolyl)amine. Tetrafluoro-p-benzoquinone and heptafluoro-p-toluquinol were obtained from N-methylpentafluoroanilinz and N-methylperfluoro-p-toluidine, respectively, under the action of a mixture of HNO3 and H2SO4 The X-ray crystal structure of N-nitro-N-methylperfluoro-p-toluidine was determined. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-1139(01)00367-0
• 作为产物：
  描述：

  氯五氟苯 以 硝基甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 2,3,4,5-Tetrafluoro-6-(methylamino)benzonitrile 、 N-Methyl-p-cyanotetrafluoroaniline
  参考文献：
  名称：

  Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: F: PerFHalOrg.9, 7, page 50 - 101

  摘要：

  DOI：

文献信息

• Kobrina,L.S. et al., Journal of Organic Chemistry USSR (English Translation), 1970, vol. 6, p. 510 - 517
  作者：Kobrina,L.S. et al.

  DOI：——

  日期：——
• Kobrina, L. S.; Furin, G. G.; Yakobson, G. G., Zhurnal Organicheskoi Khimii, 1970, vol. 6, p. 510 - 517
  作者：Kobrina, L. S.、Furin, G. G.、Yakobson, G. G.

  DOI：——

  日期：——
• Polyfluorinated arylnitrosamines
  作者：Vyacheslav E. Platonov、Alois Haas、Meinolf Schelvis、Max Lieb、Kira V. Dvornikova、Olga I. Osina、Tatyana V. Rybalova、Yuri V. Gatilov

  DOI：10.1016/s0022-1139(01)00567-x

  日期：2002.3

  N-Methyl-, N-n-butyl-, N-t-butylperfluoroarylamines undergo nitrosation with nitrous acid to give the corresponding N-nitroso derivatives. Perfluoroaryl groups were selected from the benzene, indane, biphenyl, naphthalene and pyridine series. According to H-1 and F-19 NMR spectra, N-nitroso-N-methyl derivatives of polyfluoroarenes, consist of E and Z isomers with the former prevailing. The more bulky n-butyl group promotes an increase in the formation of Z isomers. Only Z isomers have been obtained from N-t-butyl derivatives of perfluorinated 4-toluidine and 4-aminopyridine. The structure of the Z isomer of N-nitroso-N-methylperfluoro-4-toluidine is confirmed by X-ray data. (C) 2002 Elsevier Science B.V. All rights reserved.