N-(1-chloroethylidene)-4-chlorobenzenamine | 76540-13-1

• 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-(1-chloroethylidene)-4-chlorobenzenamine
• 英文别名: N-(4-chlorophenyl)acetimidoyl chloride；Ethanimidoyl chloride, N-(4-chlorophenyl)-；N-(4-chlorophenyl)ethanimidoyl chloride
• CAS: 76540-13-1
• 化学式: C₈H₇Cl₂N
• 分子量: 188.056
• InChiKey: OUEBWFJFLAAVQE-UHFFFAOYSA-N

物化性质

• 沸点：
  262.4±42.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  11
• 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：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(1-chloroethylidene)-4-chlorobenzenamine 在 potassium tellurocyanate 作用下， 以 二甲基亚砜 为溶剂， 反应 2.5h， 以63%的产率得到1,4-bis(4-chlorophenyl)-2,3-dimethyl-1,4-diaza-1,3-butadiene
  参考文献：
  名称：

  Potassium Tellurocyanate Mediated Coupling Reactions ofN-(1-Chloroethylidene)Arylamines

  摘要：

  The reaction of potassium tellurocyanate (prepared in situ) with N-(1-chloroethylidene)arylamines (i.e., 4-RC6H4N = C(CH3)Cl, where R = H, Cl, CH3 and NO2) in DMSO solution gave unexpectedly, after hydrolysis, the corresponding N-(3-(arylamino)butan-2-ylidene)arylamines in 63-78%. Reaction of N-(3-(arylamino)butan-2-ylidene)arylamines with SOCl2 or with Br-2 resulted in the substitution of a halogen on the aromatic rings. The presence of a water molecule within the structure of the synthesized diimines was rationalized theoretically by Density Functional Theory (DFT). All compounds were characterized by elemental analysis, IR, NMR and mass spectroscopic data.

  DOI：

  10.1080/10426507.2014.902830
• 作为产物：
  描述：

  对氯乙酰苯胺 在 五氯化磷 作用下， 以 苯 为溶剂， 生成 N-(1-chloroethylidene)-4-chlorobenzenamine
  参考文献：
  名称：

  Zielinski, W.; Mazik, M., Polish Journal of Chemistry, 1994, vol. 68, # 3, p. 489 - 498

  摘要：

  DOI：

文献信息

• Moerkved, Eva H., Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1980, vol. 34, # 5, p. 313 - 318
  作者：Moerkved, Eva H.

  DOI：——

  日期：——
• Zielinski, W.; Mazik, M., Polish Journal of Chemistry, 1994, vol. 68, # 3, p. 489 - 498
  作者：Zielinski, W.、Mazik, M.

  DOI：——

  日期：——
• Potassium Tellurocyanate Mediated Coupling Reactions of<i>N</i>-(1-Chloroethylidene)Arylamines
  作者：Shaker A. Al-Jadaan、Wasfi A. Al-Masoudi、Bahjat A. Saeed、Ali Z. Al-Rubaie

  DOI：10.1080/10426507.2014.902830

  日期：2014.12.2

  The reaction of potassium tellurocyanate (prepared in situ) with N-(1-chloroethylidene)arylamines (i.e., 4-RC6H4N = C(CH3)Cl, where R = H, Cl, CH3 and NO2) in DMSO solution gave unexpectedly, after hydrolysis, the corresponding N-(3-(arylamino)butan-2-ylidene)arylamines in 63-78%. Reaction of N-(3-(arylamino)butan-2-ylidene)arylamines with SOCl2 or with Br-2 resulted in the substitution of a halogen on the aromatic rings. The presence of a water molecule within the structure of the synthesized diimines was rationalized theoretically by Density Functional Theory (DFT). All compounds were characterized by elemental analysis, IR, NMR and mass spectroscopic data.