3,6-dichloro-4,5-bis(phenylsulfanyl)phthalonitrile | 162646-69-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3,6-dichloro-4,5-bis(phenylsulfanyl)phthalonitrile
• 英文别名: 3,6-dichloro-4,5-bis(phenylsulfanyl)benzene-1,2-dicarbonitrile
• CAS: 162646-69-7
• 化学式: C₂₀H₁₀Cl₂N₂S₂
• 分子量: 413.351
• InChiKey: OBBHUGYDODJANI-UHFFFAOYSA-N

物化性质

• 沸点：
  542.9±50.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  98.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,6-dichloro-4,5-bis(phenylsulfanyl)phthalonitrile 在 ammonium molybdate 、 四氯化钛 作用下， 反应 3.0h， 生成
  参考文献：
  名称：

  Phthalocyanines and related compounds: XLIII. Synthesis of poly[phenyl(alkyl)sulfanyl]-substituted phthalonitriles and some phthalocyanines based thereon

  摘要：

  Nucleophilic substitution of chlorine atoms in tetrachlorophthalonitrile by benzene- and alkanethiols in the presence of a base was studied at different reactant ratios. The substitution is characterized by complete regioselectivity: the chlorine atom in position 4 of tetrachlorophthalonitrile is replaced first; next follows replacement of the 5-chlorine atom. The reactions of tetrachlorophthalonitrile with nucleophiles at ratios of 1:2 and 1:4 lead to the formation of the corresponding 3,6-dichloro-4,5-bis[phenyl(alkyl)sulfanyl]- and tetrakis[phenyl(alkyl)sulfanyl]phthalonitriles. The latter were converted into metal complexes of [phenyl-(alkyl)sulfanyl]-substituted phthalocyanines which absorb in the red and near-IR regions of the electronic spectra.

  DOI：

  10.1134/s107036320706028x
• 作为产物：
  描述：

  3,4,5,6-四氯苯-1,2-二甲腈 、 苯硫酚 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以92%的产率得到3,6-dichloro-4,5-bis(phenylsulfanyl)phthalonitrile
  参考文献：
  名称：

  Phthalocyanines and related compounds: XLIII. Synthesis of poly[phenyl(alkyl)sulfanyl]-substituted phthalonitriles and some phthalocyanines based thereon

  摘要：

  Nucleophilic substitution of chlorine atoms in tetrachlorophthalonitrile by benzene- and alkanethiols in the presence of a base was studied at different reactant ratios. The substitution is characterized by complete regioselectivity: the chlorine atom in position 4 of tetrachlorophthalonitrile is replaced first; next follows replacement of the 5-chlorine atom. The reactions of tetrachlorophthalonitrile with nucleophiles at ratios of 1:2 and 1:4 lead to the formation of the corresponding 3,6-dichloro-4,5-bis[phenyl(alkyl)sulfanyl]- and tetrakis[phenyl(alkyl)sulfanyl]phthalonitriles. The latter were converted into metal complexes of [phenyl-(alkyl)sulfanyl]-substituted phthalocyanines which absorb in the red and near-IR regions of the electronic spectra.

  DOI：

  10.1134/s107036320706028x

文献信息

• Phthalocyanines and related compounds: XLVIII. Stepwise nucleophilic substitution in tetrachlorophthalonitrile: Synthesis of polysubstituted phthalonitriles
  作者：K. A. Volkov、V. M. Negrimovskii、G. V. Avramenko、E. A. Luk’yanets

  DOI：10.1134/s1070363208090247

  日期：2008.9

  Chlorine-containing products of incomplete nucleophilic substitution in tetrachlorophthalonitrile were subjected to further reaction with nucleophiles. The nature of the nucleophiles and the order of their introduction into stepwise nucleophilic substitution in tetrachlorophthalonitrile were shown to be of principal importance for selective synthesis on this basis of phthalonitrile derivatives with various substituents.