5-(4-cyanophenyldiazenyl)-8-hydroxyquinoline | 850234-47-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 5-(4-cyanophenyldiazenyl)-8-hydroxyquinoline
• 英文别名: 5-(4-cyanophenylazo)-8-hydroxyquinoline；4-[(8-Hydroxyquinolin-5-yl)diazenyl]benzonitrile
• CAS: 850234-47-8
• 化学式: C₁₆H₁₀N₄O
• 分子量: 274.282
• InChiKey: LQECPMUYOPGWKO-UHFFFAOYSA-N

物化性质

• 沸点：
  560.2±45.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  81.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  8-羟基喹啉 、 对氨基苯腈 在 盐酸 、 sodium nitrite 、 potassium hydroxide 、 sodium carbonate 作用下， 以 水 为溶剂， 反应 2.0h， 以80%的产率得到5-(4-cyanophenyldiazenyl)-8-hydroxyquinoline
  参考文献：
  名称：

  Azo-8-hydroxyquinoline dyes: The synthesis, characterizations and determination of tautomeric properties of some new phenyl- and heteroarylazo-8-hydroxyquinolines

  摘要：

  Two series of new heterocyclic and carbocyclic disperse azo dyes based on 8-hydroxyquinoline were prepared and characterized by FT-IR, H-1 NMR, mass spectroscopic techniques and elemental analysis. Their solvatochromic properties in different solvents were investigated and their absorption spectra were strongly solvent dependent The acid and base effects on this equilibrium were also examined. In addition, the colors of dyes were discussed with respect to the nature of the carbocyclic and heterocyclic rings and substituent therein. To determine the tautomeric forms of the prepared dyes in solid state, X-ray data for 5-(5-methylthiazol-2-yldiazenyl)-8-hydroxyquinoline were recorded. The X-ray results showed that the dye exists as an azo tautomer in the solid state. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molliq.2014.02.027

文献信息

• Tautomeric behavior of some azoquinoline dyes in liquid and liquid crystalline media
  作者：A. Ghanadzadeh Gilani、E. Moradi、S. Binay、M. Moghadam

  DOI：10.1016/j.saa.2011.11.020

  日期：2012.2

  The absorption spectra of three azoquinolin-8-ol derivatives (o-, m-, p-cyano hydroxy azoquinolin dyes) were investigated in liquid and liquid crystalline solutions as a function of the solvent polarity. The spectral data of the dyes were compared in both ordinary liquid solvents and liquid crystalline media. Analysis of the spectral data was used to determine the azo and hydrazone forms in both the environments. The spectral shifts were correlated by Kamlet-Taft and Katritzky multi-parameter polarity scales. For the azoquinoline dyes, the azo form is almost entirely dominated in polar anisotropic hosts. In contrast, the compounds remain dominantly in hydrazone form in some polar solvents such as DMF. The polarized absorption spectra of the compounds in the anisotropic media were measured and their degree of anisotropies was determined. (C) 2011 Elsevier B.V. All rights reserved.