5-chloro-1-ethyl-3-methyl-4-nitro-1H-pyrazole | 13551-74-1

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 5-chloro-1-ethyl-3-methyl-4-nitro-1H-pyrazole
• 英文别名: 5-chloro-1-ethyl-3-methyl-4-nitro-1H-pyrazole；5-chloro-1-ethyl-3-methyl-4-nitropyrazole
• CAS: 13551-74-1
• 化学式: C₆H₈ClN₃O₂
• mdl: MFCD21667720
• 分子量: 189.601
• InChiKey: JUEYFGYMSCITJF-UHFFFAOYSA-N

物化性质

• 熔点：
  37 °C
• 沸点：
  286.7±35.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  63.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-chloro-1-ethyl-3-methyl-1H-pyrazole 在 硫酸 、 硝酸 作用下， 反应 8.0h， 以60%的产率得到5-chloro-1-ethyl-3-methyl-4-nitro-1H-pyrazole
  参考文献：
  名称：

  Synthesis and properties of 5-chloro-4-nitropyrazoles

  摘要：

  The nitration of 5-chloropyrazoles with a mixture of 100% nitric acid and 65% oleum or a mixture of 60% nitric acid and polyphosphoric acid gave substituted 5-chloro-4-nitropyrazoles in 45-91% yield. The nitration of 3-aryl-5-halopyrazoles was accompanied by introduction of a nitro group into the aromatic ring. 4-Chloropyrazoles failed to undergo nitration under these conditions. The reaction of 5-chloro-1,3-dimethyl-4-nitropyrazole with ethyl cyanoacetate in DMSO in the presence of K2CO3 led to the formation of ethyl 2-cyano-2-(1,3-dimethyl-4-nitro-1H-pyrazol-5-yl)acetate.

  DOI：

  10.1134/s1070428006060157

文献信息

• Synthesis and properties of 5-chloro-4-nitropyrazoles
  作者：G. V. Bozhenkov、V. A. Savosik、L. I. Larina、A. N. Mirskova、G. G. Levkovskaya

  DOI：10.1134/s1070428006060157

  日期：2006.6

  The nitration of 5-chloropyrazoles with a mixture of 100% nitric acid and 65% oleum or a mixture of 60% nitric acid and polyphosphoric acid gave substituted 5-chloro-4-nitropyrazoles in 45-91% yield. The nitration of 3-aryl-5-halopyrazoles was accompanied by introduction of a nitro group into the aromatic ring. 4-Chloropyrazoles failed to undergo nitration under these conditions. The reaction of 5-chloro-1,3-dimethyl-4-nitropyrazole with ethyl cyanoacetate in DMSO in the presence of K2CO3 led to the formation of ethyl 2-cyano-2-(1,3-dimethyl-4-nitro-1H-pyrazol-5-yl)acetate.