3,4-Dicyano-2,5,6-trichlordiphenylamin | 25579-62-8

• 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: 3,4-Dicyano-2,5,6-trichlordiphenylamin
• 英文别名: 4-phenylamino-3,5,6-trichlorophthalonitrile；3,5,6-trichloro-4-phenylamino-phthalonitrile；4-Anilino-3,5,6-trichlorobenzene-1,2-dicarbonitrile；4-anilino-3,5,6-trichlorobenzene-1,2-dicarbonitrile
• CAS: 25579-62-8
• 化学式: C₁₄H₆Cl₃N₃
• 分子量: 322.581
• InChiKey: CLTJDOUZSGONOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  59.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4-Dicyano-2,5,6-trichlordiphenylamin 在 zinc diacetate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 戊醇 为溶剂， 反应 2.0h， 以40%的产率得到zinc tetraphenylaminododecachlorophthalocyanine
  参考文献：
  名称：

  Phthalocyanines and related compounds: XLVII. Nucleophilic replacement of chlorine atoms in tetrachlorophthalonitrile. Synthesis of phenyl(alkyl)amino-substituted phthalonitriles and some phthalocyanines based thereon

  摘要：

  Nucleophilic replacement of chlorine atoms in tetrachlorophthalonitrile by the action of primary and secondary amines was studied. The reactions of tetrachlorophthalonitrile with amines at a ratio of 1: 10 gave with high yields and regioselectivity the corresponding 4,5-diamino-3,6-dichlorophthalonitriles from cyclic secondary amines and 4-amino-3,5,6-trichlorophthalonitriles from primary amines and acyclic secondary amines. 4-Amino-3,5,6-trichlorophthalonitriles were used to synthesize cobalt and zinc phthalocyanine complexes. It was shown that replacement of chlorine atoms in the pyrrolic beta-positions of hexadecachlorophthalocyanines by amino groups is not accompanied by red shift of the long-wave absorption band in the electronic spectra.

  DOI：

  10.1134/s1070363208090235
• 作为产物：
  描述：

  3,4,5,6-四氯苯-1,2-二甲腈 、 苯胺 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以65%的产率得到3,4-Dicyano-2,5,6-trichlordiphenylamin
  参考文献：
  名称：

  Phthalocyanines and related compounds: XLVII. Nucleophilic replacement of chlorine atoms in tetrachlorophthalonitrile. Synthesis of phenyl(alkyl)amino-substituted phthalonitriles and some phthalocyanines based thereon

  摘要：

  Nucleophilic replacement of chlorine atoms in tetrachlorophthalonitrile by the action of primary and secondary amines was studied. The reactions of tetrachlorophthalonitrile with amines at a ratio of 1: 10 gave with high yields and regioselectivity the corresponding 4,5-diamino-3,6-dichlorophthalonitriles from cyclic secondary amines and 4-amino-3,5,6-trichlorophthalonitriles from primary amines and acyclic secondary amines. 4-Amino-3,5,6-trichlorophthalonitriles were used to synthesize cobalt and zinc phthalocyanine complexes. It was shown that replacement of chlorine atoms in the pyrrolic beta-positions of hexadecachlorophthalocyanines by amino groups is not accompanied by red shift of the long-wave absorption band in the electronic spectra.

  DOI：

  10.1134/s1070363208090235

文献信息

• SUBSTITUTED CYANOANILINE COMPOUNDS, PREPARATION AND USE THEREOF
  申请人：Liu Changling

  公开号：US20140213598A1

  公开（公告）日：2014-07-31

  Disclosed is a substituted cyanoaniline compound or a salt thereof, wherein the compound has a structure represented by General Formula I. The compound of General Formula I has broad-spectrum fungicidal activity in the field of agriculture and effectively prevents against a variety of pathogens such as cucumber downy mildew, wheat powdery mildew, maize rust disease, rice blast and cucumber gray mold. In particular, even at a low dose, the compound effectively prevents and treats rice blast, cucumber gray mold, maize rust disease and cucumber downy mildew. Moreover, the raw materials for preparing the compounds are widely available and the synthesis method therefor is simple and convenient.

  揭示了一种取代的氰基苯胺化合物或其盐，其中该化合物具有由一般式I表示的结构。一般式I的化合物在农业领域具有广谱杀菌活性，并有效预防多种病原体，如黄瓜霜霉病、小麦白粉病、玉米锈病、稻瘟病和黄瓜灰霉病。特别是，即使在低剂量下，该化合物也能有效预防和治疗稻瘟病、黄瓜灰霉病、玉米锈病和黄瓜霜霉病。此外，用于制备这些化合物的原材料广泛可得，其合成方法简单方便。
• [EN] SUBSTITUTED CYANOANILINE COMPOUNDS, PREPARATION AND USE THEREOF<br/>[FR] COMPOSÉS DE CYANOANILINE SUBSTITUÉS, LEUR PRÉPARATION ET LEUR UTILISATION
  申请人：SINOCHEM CORP

  公开号：WO2012171484A1

  公开（公告）日：2012-12-20

  一种取代氰基苯胺类化合物或其盐，化合物结构如通式I所示：通式I化合物在农业领域中具有光谱的杀菌活性，对黄瓜霜霉病、小麦白粉病、玉米锈病、稻瘟病、黄瓜灰霉病等多种病菌都有很好的防效。特别地，对稻瘟病、黄瓜灰霉病、玉米锈病和黄瓜霜霉病，在较低剂量下仍具有很好的防治效果。而且制备该类化合物的原料易得，合成方法简便。
• 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.
• US8937072B2
  申请人：——

  公开号：US8937072B2

  公开（公告）日：2015-01-20
• Phthalocyanines and related compounds: XLVII. Nucleophilic replacement of chlorine atoms in tetrachlorophthalonitrile. Synthesis of phenyl(alkyl)amino-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/s1070363208090235

  日期：2008.9

  Nucleophilic replacement of chlorine atoms in tetrachlorophthalonitrile by the action of primary and secondary amines was studied. The reactions of tetrachlorophthalonitrile with amines at a ratio of 1: 10 gave with high yields and regioselectivity the corresponding 4,5-diamino-3,6-dichlorophthalonitriles from cyclic secondary amines and 4-amino-3,5,6-trichlorophthalonitriles from primary amines and acyclic secondary amines. 4-Amino-3,5,6-trichlorophthalonitriles were used to synthesize cobalt and zinc phthalocyanine complexes. It was shown that replacement of chlorine atoms in the pyrrolic beta-positions of hexadecachlorophthalocyanines by amino groups is not accompanied by red shift of the long-wave absorption band in the electronic spectra.