4-(2,5-dimethoxyphenyl)phthalonitrile | 249557-43-5

• 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: 4-(2,5-dimethoxyphenyl)phthalonitrile
• 英文别名: 4-(2,5-Dimethoxyphenyl)benzene-1,2-dicarbonitrile
• CAS: 249557-43-5
• 化学式: C₁₆H₁₂N₂O₂
• 分子量: 264.283
• InChiKey: WMVJSKYMZBSDRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  66
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(2,5-dimethoxyphenyl)phthalonitrile 在 lithium 作用下， 以 正丁醇 为溶剂， 反应 1.0h， 以27%的产率得到tetra(2,5-dimethoxyphenyl)phthalocyanine
  参考文献：
  名称：

  An Application of the Stille Coupling for the Preparation of Arylated Phthalonitriles and Phthalocyanines.

  摘要：

  The substituted phthalonitriles 4-phenylphthalonitrile (2a), 4-(2,5-dimethoxyphenyl) phthalonitrile(2b) and 2-(3,4-dicyanophenyl)-4-methylpyridine(2c) have been prepared in good yields from 4-iodophthalonitrile 3, the synthesis of which is also discussed, using the Stille coupling method. Such phthalonitriles are precursors for phthalocyanines with the possibility of biphenyl-like orientation of a peripheral substituent with respect to the macrocycle ring plane. As an example, 2b was used in the preparation of tetra(dimethoxyphenyl)phthalocyanine 1a. Both 1a and the corresponding zinc(II) complex show good solubility in non-polar solvents such as dichloromethane.

  DOI：

  10.3891/acta.chem.scand.53-0714
• 作为产物：
  描述：

  4-硝基邻苯二甲酰胺 在 palladium on activated charcoal tris(dibenzylideneacetone)dipalladium (0) 、 氢气 、 三氟乙酸酐 、 sodium nitrite 作用下， 以 1,4-二氧六环 、 吡啶 、 乙醇 、 硫酸 、 N,N-二甲基甲酰胺 为溶剂， -5.0~50.0 ℃ 、380.0 kPa 条件下， 反应 50.0h， 生成 4-(2,5-dimethoxyphenyl)phthalonitrile
  参考文献：
  名称：

  An Application of the Stille Coupling for the Preparation of Arylated Phthalonitriles and Phthalocyanines.

  摘要：

  The substituted phthalonitriles 4-phenylphthalonitrile (2a), 4-(2,5-dimethoxyphenyl) phthalonitrile(2b) and 2-(3,4-dicyanophenyl)-4-methylpyridine(2c) have been prepared in good yields from 4-iodophthalonitrile 3, the synthesis of which is also discussed, using the Stille coupling method. Such phthalonitriles are precursors for phthalocyanines with the possibility of biphenyl-like orientation of a peripheral substituent with respect to the macrocycle ring plane. As an example, 2b was used in the preparation of tetra(dimethoxyphenyl)phthalocyanine 1a. Both 1a and the corresponding zinc(II) complex show good solubility in non-polar solvents such as dichloromethane.

  DOI：

  10.3891/acta.chem.scand.53-0714

文献信息

• An Application of the Stille Coupling for the Preparation of Arylated Phthalonitriles and Phthalocyanines.
  作者：Viviane Aranyos、Ana M. Castaño、Helena Grennberg、M. Frederick Hawthorne、Stefan Sjöberg、André Tallec、Tatsuya Shono、H. Toftlund

  DOI：10.3891/acta.chem.scand.53-0714

  日期：——

  The substituted phthalonitriles 4-phenylphthalonitrile (2a), 4-(2,5-dimethoxyphenyl) phthalonitrile(2b) and 2-(3,4-dicyanophenyl)-4-methylpyridine(2c) have been prepared in good yields from 4-iodophthalonitrile 3, the synthesis of which is also discussed, using the Stille coupling method. Such phthalonitriles are precursors for phthalocyanines with the possibility of biphenyl-like orientation of a peripheral substituent with respect to the macrocycle ring plane. As an example, 2b was used in the preparation of tetra(dimethoxyphenyl)phthalocyanine 1a. Both 1a and the corresponding zinc(II) complex show good solubility in non-polar solvents such as dichloromethane.