4-[(4-chloro-2-nitrophenyl)hydrazinylidene]-5-methyl-2-phenylpyrazol-3-one | 92853-99-1

• 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-[(4-chloro-2-nitrophenyl)hydrazinylidene]-5-methyl-2-phenylpyrazol-3-one
• CAS: 92853-99-1
• 化学式: C₁₆H₁₂ClN₅O₃
• 分子量: 357.756
• InChiKey: QHPYIXXVJIZXLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.44
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  100.2
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-[(4-chloro-2-nitrophenyl)hydrazinylidene]-5-methyl-2-phenylpyrazol-3-one 在 二氧化硫脲 、 sodium hydroxide 、 盐酸 作用下， 以 水 为溶剂， 反应 3.0h， 以88%的产率得到4-(5-chloro-2-benzotriazolyl)-5-methyl-2-phenyl-3-pyrazolone
  参考文献：
  名称：

  Synthesis, spectroscopic properties and applications of novel N-heterocycle-containing benzotriazoles as UV absorbers

  摘要：

  Two novel N-heterocycle-containing benzotriazole compounds, 5-(5-chloro-2-benzotriazolyl)-6-hydroxy-1,4-dimethyl-3-carbonitrile-2-pyridone (2) and 4-(5-chloro-2-benzotriazolyl)-5-methyl-2-phenyl-3-pyrazolone (4), were synthesized from reactant 4-chloro-2-nitroaniline via diazotization, azo coupling, reductive cyclization and acidification. Their structures were confirmed by FT-IR. H-1 NMR, mass spectroscopy and elemental analysis. Their spectral properties were investigated and compared with that of a common commercial benzotriazole UV absorber Tinuvin 326. It is found that the novel N-heterocycle-containing benzotriazole compounds exhibit sharp single peak in the range of 280-400 nm and have much higher molar extinction coefficients than that of Tinuvin 326. Their anti-UV protection properties on polyester fabric were also evaluated and compound 4 was much superior to compound 2 due to its higher exhaustion. (C) 2012 Zhi Hua Cui. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2012.06.024
• 作为产物：
  描述：

  4-氯-2-硝基苯胺 、 依达拉奉 在 盐酸 、 sodium nitrite 作用下， 生成 4-[(4-chloro-2-nitrophenyl)hydrazinylidene]-5-methyl-2-phenylpyrazol-3-one
  参考文献：
  名称：

  Synthesis, spectroscopic properties and applications of novel N-heterocycle-containing benzotriazoles as UV absorbers

  摘要：

  Two novel N-heterocycle-containing benzotriazole compounds, 5-(5-chloro-2-benzotriazolyl)-6-hydroxy-1,4-dimethyl-3-carbonitrile-2-pyridone (2) and 4-(5-chloro-2-benzotriazolyl)-5-methyl-2-phenyl-3-pyrazolone (4), were synthesized from reactant 4-chloro-2-nitroaniline via diazotization, azo coupling, reductive cyclization and acidification. Their structures were confirmed by FT-IR. H-1 NMR, mass spectroscopy and elemental analysis. Their spectral properties were investigated and compared with that of a common commercial benzotriazole UV absorber Tinuvin 326. It is found that the novel N-heterocycle-containing benzotriazole compounds exhibit sharp single peak in the range of 280-400 nm and have much higher molar extinction coefficients than that of Tinuvin 326. Their anti-UV protection properties on polyester fabric were also evaluated and compound 4 was much superior to compound 2 due to its higher exhaustion. (C) 2012 Zhi Hua Cui. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2012.06.024

文献信息

• Synthesis, spectroscopic properties and applications of novel N-heterocycle-containing benzotriazoles as UV absorbers
  作者：Zhi Hua Cui、Xi Dong Wang、Jiang Chao Guo、Wei Guo Chen

  DOI：10.1016/j.cclet.2012.06.024

  日期：2012.9

  Two novel N-heterocycle-containing benzotriazole compounds, 5-(5-chloro-2-benzotriazolyl)-6-hydroxy-1,4-dimethyl-3-carbonitrile-2-pyridone (2) and 4-(5-chloro-2-benzotriazolyl)-5-methyl-2-phenyl-3-pyrazolone (4), were synthesized from reactant 4-chloro-2-nitroaniline via diazotization, azo coupling, reductive cyclization and acidification. Their structures were confirmed by FT-IR. H-1 NMR, mass spectroscopy and elemental analysis. Their spectral properties were investigated and compared with that of a common commercial benzotriazole UV absorber Tinuvin 326. It is found that the novel N-heterocycle-containing benzotriazole compounds exhibit sharp single peak in the range of 280-400 nm and have much higher molar extinction coefficients than that of Tinuvin 326. Their anti-UV protection properties on polyester fabric were also evaluated and compound 4 was much superior to compound 2 due to its higher exhaustion. (C) 2012 Zhi Hua Cui. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.