5-hydroxy-2-(phenylazo)benzenesulfonic acid | 72792-36-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: 5-hydroxy-2-(phenylazo)benzenesulfonic acid
• 英文别名: 4-Benzolazo-3-sulfonylphenol；5-hydroxy-2-[(E)-phenyldiazenyl]benzenesulfonic acid；5-hydroxy-2-phenyldiazenylbenzenesulfonic acid
• CAS: 72792-36-0
• 化学式: C₁₂H₁₀N₂O₄S
• 分子量: 278.288
• InChiKey: CXXRIFMOUWHRQN-UHFFFAOYSA-N

物化性质

• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-氨基苯磺酸 在 sodium hydroxide 、 硫酸 、 sodium nitrite 作用下， 以 水 为溶剂， 生成 5-hydroxy-2-(phenylazo)benzenesulfonic acid
  参考文献：
  名称：

  Effect of Substituent in Diazotized Orthanilic Acid on the Azo Coupling with 7-Acetylamino-4-hydroxynaphthalene-2-sulfonic Acid in Citrate-Phosphate Buffers

  摘要：

  Effect of substituent in the para position with respect to the diazo group in diazotized orthanilic acid derivatives on the rate and selectivity of azo coupling with 7-acetylamino-4-hydroxynaphthalene-2-sulfonic acid was studied in citrate-phosphate buffers. The selectivity of azo coupling at the 3-position of the azo component almost does not depend on the nature of electron-donor substituent. Electron-acceptor groups considerably reduce the selectivity of formation of the 3-isomer. Previous conclusions, according to which the rate-determining stages are different depending on the site of azo coupling of diazotized orthanilic acid with 7-acetylamino-4-hydroxynaphthalene-2-sulfonic acid, were found to be also valid for some 5-substituted orthanilic acid derivatives. The rate-determining stage in the azo coupling at the 3-position can change upon introduction of strong electron-acceptor substituents capable of interacting with the diazo group. The contribution of the multicenter mechanism of deprotonation of the sigma-complex with participation of water molecules was presumed to increase in going to the diazo components having electron-donor substituents.

  DOI：

  10.1023/b:rugc.0000007618.08375.43