3,6-dichloro-4,5-bis(n-butylsulfanyl)phthalonitrile | 1062221-95-7

• 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: 3,6-dichloro-4,5-bis(n-butylsulfanyl)phthalonitrile
• 英文别名: 4,5-Bis(butylsulfanyl)-3,6-dichlorobenzene-1,2-dicarbonitrile
• CAS: 1062221-95-7
• 化学式: C₁₆H₁₈Cl₂N₂S₂
• 分子量: 373.37
• InChiKey: DLTCNGKVBMGVFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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(n-butylsulfanyl)phthalonitrile 在 ammonium molybdate 、 copper dichloride 作用下， 反应 3.0h， 生成 Copper;6,7,15,16,24,25,33,34-octakis(butylsulfanyl)-5,8,14,17,23,26,32,35-octachloro-2,11,20,29,37,39-hexaza-38,40-diazanidanonacyclo[28.6.1.13,10.112,19.121,28.04,9.013,18.022,27.031,36]tetraconta-1,3,5,7,9,11,13(18),14,16,19(39),20,22(27),23,25,28,30(37),31(36),32,34-nonadecaene
  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：

  丁硫醇 、 3,4,5,6-四氯苯-1,2-二甲腈 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以91%的产率得到3,6-dichloro-4,5-bis(n-butylsulfanyl)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