3-(4-chloro-5H-1,2,3-dithiazol-5-ylideneamino)-3-chloro-2-(methylthio)acrylonitrile | 1187823-93-3

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 3-(4-chloro-5H-1,2,3-dithiazol-5-ylideneamino)-3-chloro-2-(methylthio)acrylonitrile
• CAS: 1187823-93-3
• 化学式: C₆H₃Cl₂N₃S₃
• 分子量: 284.214
• InChiKey: JBSBRBILSFPINP-UHFFFAOYSA-N

物化性质

• 熔点：
  136-138 °C(Solv: cyclohexane (110-82-7))
• 沸点：
  367.1±52.0 °C(Predicted)
• 密度：
  1.68±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.05
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  49.04
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  dimethylsulfonium dicyanomethylide 、 4,5-二氯-1,2,3-二噻唑氯化物 以 乙腈 为溶剂， 反应 3.0h， 以7%的产率得到4-chloro-5H-1,2,3-dithiazole-5-thione
  参考文献：
  名称：

  The reaction of 4,5-dichloro-1,2,3-dithiazolium chloride with dimethylsulfonium dicyanomethylide: an improved synthesis of (4-chloro-1,2,3-dithiazolylidene)malononitrile

  摘要：

  4,5-Dichloro-1,2,3-dithiazolium chloride 6 (Appel salt) reacts with dimethylsulfonium dicyanomethylide 11 to give 5-(4-chloro-1,2,3-dithiazolylidene)malononitrile 1 and a mixture of E/Z isomers of 3-(4-chloro-5H-1,2,3-dithiazol-5-ylideneamino)-3-chloro-2-(methylthio)acrylonitrile 13. The reaction of 4-chloro-5H-1,2,3-dithiazole-5-thione 10 with dimethylsulfonium dicyanomethylide 11 gives (dithiazolylidene)malononitrile 1 in 92% yield. All new compounds are fully characterised and rational mechanisms are proposed for the formation of all key compounds. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.06.076

文献信息

• The reaction of 4,5-dichloro-1,2,3-dithiazolium chloride with dimethylsulfonium dicyanomethylide: an improved synthesis of (4-chloro-1,2,3-dithiazolylidene)malononitrile
  作者：Andreas S. Kalogirou、Panayiotis A. Koutentis

  DOI：10.1016/j.tet.2009.06.076

  日期：2009.8

  4,5-Dichloro-1,2,3-dithiazolium chloride 6 (Appel salt) reacts with dimethylsulfonium dicyanomethylide 11 to give 5-(4-chloro-1,2,3-dithiazolylidene)malononitrile 1 and a mixture of E/Z isomers of 3-(4-chloro-5H-1,2,3-dithiazol-5-ylideneamino)-3-chloro-2-(methylthio)acrylonitrile 13. The reaction of 4-chloro-5H-1,2,3-dithiazole-5-thione 10 with dimethylsulfonium dicyanomethylide 11 gives (dithiazolylidene)malononitrile 1 in 92% yield. All new compounds are fully characterised and rational mechanisms are proposed for the formation of all key compounds. (C) 2009 Elsevier Ltd. All rights reserved.