5-chloro-3-(1-chloroethyl)-1-methyl-1H-pyrazole | 1278588-14-9

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 5-chloro-3-(1-chloroethyl)-1-methyl-1H-pyrazole
• 英文别名: 5-Chloro-3-(1-chloroethyl)-1-methyl-1h-pyrazole；5-chloro-3-(1-chloroethyl)-1-methylpyrazole
• CAS: 1278588-14-9
• 化学式: C₆H₈Cl₂N₂
• 分子量: 179.049
• InChiKey: GEXFNALHPVOBEO-UHFFFAOYSA-N

物化性质

• 沸点：
  100-102 °C(Press: 15 Torr)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  10
• 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：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-chloro-3-(1-chloroethyl)-1-methyl-1H-pyrazole 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以72%的产率得到5-chloro-3-ethenyl-1-methyl-1H-pyrazole
  参考文献：
  名称：

  3-Alkenyl-5-chloropyrazoles: expedient synthesis via heterocyclization of 1,1-dichloro-4-halo-1-alken-3-ones with hydrazines

  摘要：

  Synthesis of hard-to-reach 5-chloro-3-alkenylpyrazoles was developed via heterocyclization of alkyl-, benzyl- or dialkylhydrazines with 1,1-dichloro-4-halo-1-alken-3-ones obtained from haloacyl chlorides and vinylidene chloride. The reaction process includes the formation of intermediate 5-chloro-3-(1-haloalkyl)pyrazoles followed by dehydrohalogenation. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.028
• 作为产物：
  描述：

  2,2-dichlorovinyl 1-chloroethyl ketone 、 偏二甲肼 在 三乙胺 作用下， 以 乙醚 为溶剂， 反应 5.0h， 以80%的产率得到5-chloro-3-(1-chloroethyl)-1-methyl-1H-pyrazole
  参考文献：
  名称：

  3-Alkenyl-5-chloropyrazoles: expedient synthesis via heterocyclization of 1,1-dichloro-4-halo-1-alken-3-ones with hydrazines

  摘要：

  Synthesis of hard-to-reach 5-chloro-3-alkenylpyrazoles was developed via heterocyclization of alkyl-, benzyl- or dialkylhydrazines with 1,1-dichloro-4-halo-1-alken-3-ones obtained from haloacyl chlorides and vinylidene chloride. The reaction process includes the formation of intermediate 5-chloro-3-(1-haloalkyl)pyrazoles followed by dehydrohalogenation. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.028

文献信息

• Synthesis of poly-functionalized pyrazoles under Vilsmeier-Haack reaction conditions
  作者：Aleksandr V. Popov、Valentina A. Kobelevskaya、Ludmila I. Larina、Igor B. Rozentsveig

  DOI：10.24820/ark.5550190.p010.934

  日期：——

  Synthesis of 1,3-disubstituted 5-chloro-1H-pyrazole-4-carbaldehydes was achieved by formylation of the corresponding 5-chloro-1H-pyrazoles under Vilsmeier-Haack conditions.

  1,3-二取代的 5-氯-1H-吡唑-4-甲醛的合成是通过在 Vilsmeier-Haack 条件下相应的 5-氯-1H-吡唑的甲酰化来实现的。
• Selective synthesis of 3-[1-(organylsulfanyl)ethyl]- and 3-[2-(organylsulfanyl)ethyl]-5-chloro-1H-pyrazoles
  作者：D. O. Samultsev、E. V. Rudyakova、G. G. Levkovskaya

  DOI：10.1134/s1070428012100259

  日期：2012.10
• 3-Alkenyl-5-chloropyrazoles: expedient synthesis via heterocyclization of 1,1-dichloro-4-halo-1-alken-3-ones with hydrazines
  作者：Galina G. Levkovskaya、Valentina A. Kobelevskaya、Elena V. Rudyakova、Khanh Q. Ha、Dmitrii O. Samultsev、Igor B. Rozentsveig

  DOI：10.1016/j.tet.2011.01.028

  日期：2011.3

  Synthesis of hard-to-reach 5-chloro-3-alkenylpyrazoles was developed via heterocyclization of alkyl-, benzyl- or dialkylhydrazines with 1,1-dichloro-4-halo-1-alken-3-ones obtained from haloacyl chlorides and vinylidene chloride. The reaction process includes the formation of intermediate 5-chloro-3-(1-haloalkyl)pyrazoles followed by dehydrohalogenation. (C) 2011 Elsevier Ltd. All rights reserved.