tetrakis(phenylsulfanyl)phthalonitrile | 25693-95-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: tetrakis(phenylsulfanyl)phthalonitrile
• 英文别名: Tetrakisphenylthiophthalonitril；3,4,5,6-Tetrakis(phenylsulfanyl)benzene-1,2-dicarbonitrile
• CAS: 25693-95-2
• 化学式: C₃₂H₂₀N₂S₄
• mdl: MFCD00561280
• 分子量: 560.788
• InChiKey: ORLOPWKTELNWMI-UHFFFAOYSA-N

物化性质

• 熔点：
  152-153 °C
• 沸点：
  704.7±60.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  149
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tetrakis(phenylsulfanyl)phthalonitrile 在 ammonium molybdate 、 zinc diacetate 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93%的产率得到tetrakis(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

• Method for producing of phthalocyanine compound
  申请人：NIPPON SHOKUBAI CO., LTD.

  公开号：EP0882768A2

  公开（公告）日：1998-12-09

  A method for producing a novel phthalocyanine compound which excels in yield and purity, allows no introduction of a chlorine atom into the phthalocyanine skeleton, and possesses relatively bulky substituents is provided. This method is characterized by causing an orthophthalonitrile compound having a substituent exhibiting smaller σp values than σm values in the Hammett's rule to react with a metal oxide in the presence of a compound forming in the aqueous solution thereof at 25°C an acid or conjugate acid having a dissociation index pKa (the logarithmic value of the reciprocal of the dissociation constant of the acid or conjugate acid) of not more than 7.0.

  本发明提供了一种生产新型酞菁化合物的方法，该方法产量高、纯度高，不允许在酞菁骨架中引入氯原子，并具有相对笨重的取代基。 该方法的特点是，在 25°C 时，在其水溶液中形成的酸或共轭酸的化合物存在下，使具有取代基的 σp 值小于哈密特规则中的σm 值的邻苯二甲腈化合物与金属氧化物反应，该酸或共轭酸的离解指数 pKa（酸或共轭酸的离解常数倒数的对数值）不大于 7.0。
• 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.
• US6034236A
  申请人：——

  公开号：US6034236A

  公开（公告）日：2000-03-07
• Phthalocyanines and related compounds: XLIII. Synthesis of poly[phenyl(alkyl)sulfanyl]-substituted phthalonitriles and some phthalocyanines based thereon
  作者：K. A. Volkov、G. V. Avramenko、V. M. Negrimovskii、E. A. Luk’yanets

  DOI：10.1134/s107036320706028x

  日期：2007.6

  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.