4-<(p-toluenesulfonyl)amino>benzotriazole | 137434-66-3

• 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-<(p-toluenesulfonyl)amino>benzotriazole
• 英文别名: N-(2H-benzotriazol-4-yl)-4-methylbenzenesulfonamide
• CAS: 137434-66-3
• 化学式: C₁₃H₁₂N₄O₂S
• 分子量: 288.33
• InChiKey: SQVRYYDGDFNWTK-UHFFFAOYSA-N

物化性质

• 沸点：
  571.6±52.0 °C(Predicted)
• 密度：
  1.488±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  96.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-<(p-toluenesulfonyl)amino>benzotriazole 、 苯磺酰氯 在 吡啶 作用下， 反应 1.0h， 以83%的产率得到4-<(p-toluenesulfonyl)amino>-1-(p-toluenesulfonyl)benzotriazole
  参考文献：
  名称：

  Novel Dimroth rearrangements of the benzotriazole system: 4-amino-1-(arylsulfonyl)benzotriazoles to 4-[(arylsulfonyl)amino]benzotriazoles

  摘要：

  A variety of mono- and diarylsulfonyl-substituted 4-aminobenzotriazoles were prepared. Thermal rearrangements of 4-amino-1-(arylsulfonyl)benzotriazoles to 4-[(arylsulfonyl)amino]benzotriazoles were observed and confirmed by separation of the rearrangement products. Their structures were characterized by spectral methods and by X-ray crystallography. The rearrangement rates were studied by variable-temperature NMR experiments. Crossover experiments support an intramolecular mechanism involving a heterolytic benzotriazole ring cleavage to form a diazo intermediate followed by recyclization to the 4-amino group.

  DOI：

  10.1021/jo00027a036
• 作为产物：
  描述：

  5-甲基苯并三氮唑 在 palladium on activated charcoal 吡啶 、 硫酸 、 氢气 、 硝酸 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、413.69 kPa 条件下， 反应 4.0h， 生成 4-<(p-toluenesulfonyl)amino>benzotriazole
  参考文献：
  名称：

  Novel Dimroth rearrangements of the benzotriazole system: 4-amino-1-(arylsulfonyl)benzotriazoles to 4-[(arylsulfonyl)amino]benzotriazoles

  摘要：

  A variety of mono- and diarylsulfonyl-substituted 4-aminobenzotriazoles were prepared. Thermal rearrangements of 4-amino-1-(arylsulfonyl)benzotriazoles to 4-[(arylsulfonyl)amino]benzotriazoles were observed and confirmed by separation of the rearrangement products. Their structures were characterized by spectral methods and by X-ray crystallography. The rearrangement rates were studied by variable-temperature NMR experiments. Crossover experiments support an intramolecular mechanism involving a heterolytic benzotriazole ring cleavage to form a diazo intermediate followed by recyclization to the 4-amino group.

  DOI：

  10.1021/jo00027a036

文献信息

• Novel Dimroth rearrangements of the benzotriazole system: 4-amino-1-(arylsulfonyl)benzotriazoles to 4-[(arylsulfonyl)amino]benzotriazoles
  作者：Alan R. Katritzky、Fu Bao Ji、Wei Qiang Fan、John K. Gallos、John V. Greenhill、Roy W. King、Peter J. Steel

  DOI：10.1021/jo00027a036

  日期：1992.1

  A variety of mono- and diarylsulfonyl-substituted 4-aminobenzotriazoles were prepared. Thermal rearrangements of 4-amino-1-(arylsulfonyl)benzotriazoles to 4-[(arylsulfonyl)amino]benzotriazoles were observed and confirmed by separation of the rearrangement products. Their structures were characterized by spectral methods and by X-ray crystallography. The rearrangement rates were studied by variable-temperature NMR experiments. Crossover experiments support an intramolecular mechanism involving a heterolytic benzotriazole ring cleavage to form a diazo intermediate followed by recyclization to the 4-amino group.