5-chloro-1-ethyl-3-methyl-1H-pyrazole | 31272-06-7

• 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-1-ethyl-3-methyl-1H-pyrazole
• 英文别名: 1-ethyl-3-methyl-5-chloropyrazole；5-Chlor-1-ethyl-3-methylpyrazol；1-ethyl-5-chloro-3-methyl-1H-pyrazole；1-Aethyl-5-chlor-3-methyl-1H-pyrazol；5-chloro-1-ethyl-3-methylpyrazole
• CAS: 31272-06-7
• 化学式: C₆H₉ClN₂
• mdl: MFCD04035705
• 分子量: 144.604
• InChiKey: ZLNJYINENJTGCF-UHFFFAOYSA-N

物化性质

• 沸点：
  167 °C
• 密度：
  1.0934 g/cm3(Temp: 17.2 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  9
• 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-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
• 作为产物：
  描述：

  乙基肼 、 4,4-dichlorobut-3-en-2-one 以 乙醚 为溶剂， 以66%的产率得到5-chloro-1-ethyl-3-methyl-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 Structure of 4-Trifluoromethylsulfonamidotrichloroethyl-5-chloropyrazoles
  作者：E. V. Kondrashov、I. B. Rozentsveig、G. I. Sarapulova、L. I. Larina、G. G. Levkovskaya、V. A. Savosik、G. V. Bozhenkov、A. N. Mirskova

  DOI：10.1007/s11178-005-0234-7

  日期：2005.5

  Reactions of trifluoromethanesulfonic acid N-(2,2,2-trichloroethylidene)amide with 1,3-dialkyl-5-chloropyrazoles and 1-phenyl-3-methylpyrazole afforded 4-(amidotrichloroethyl)-substituted pyrazole derivatives. 4-Chloropyrazoles were not involved into this process. The structure of compounds synthesized was studied by means of IR and NMR spectroscopy. The presence of intra- and intermolecular hydrogen bonds was revealed by a decrease in the absorption frequencies and a complicated form of ν(NH) and νas(SO2) absorption bands in the IR spectra, and also in splitting of signals in 1H and 13C NMR spectra.

  三氟甲磺酸N-(2,2,2-三氯亚乙基)酰胺与1,3-二烷基-5-氯吡唑和1-苯基-3-甲基吡唑的反应得到4-(酰氨基三氯乙基)-取代的吡唑衍生物。 4-氯吡唑类不参与该过程。通过红外光谱和核磁共振光谱研究了合成的化合物的结构。红外光谱中吸收频率的降低以及 ν(NH) 和 νas(SO2) 吸收带的复杂形式以及 1H 和 13C NMR 中信号的分裂揭示了分子内和分子间氢键的存在光谱。
• [EN] PYRAZOLE AMIDE COMPOUND AND APPLICATION THEREOF AS HERBICIDE<br/>[FR] COMPOSÉ DE PYRAZOLE AMIDE ET UTILISATION DE CELUI-CI EN TANT QU'HERBICIDE<br/>[ZH] 一种吡唑酰胺类化合物及其作为除草剂的用途
  申请人：SHENYANG SINOCHEM AGROCHEMICALS R & D CO LTD

  公开号：WO2020119612A1

  公开（公告）日：2020-06-18

  一种吡唑酰胺类化合物及其作为除草剂的应用，所述化合物如通式(I)所示，通式I化合物具有除草活性，可用于防治农业杂草，
• Chloro(bromo)vinyl ketones and 2,2-Dichloroacrolein in Reactions with Hydrazines
  作者：G. V. Bozhenkov、G. G. Levkovskaya、A. N. Mirskova、G. V. Dolgushin、L. I. Larina、P. E. Ushakov

  DOI：10.1023/b:rujo.0000010172.72180.4f

  日期：2003.8

  Reactions of 2,2-dichlorovinyl and 2,2-dibromovinyl ketones with alkylhydrazines afford respectively 1-R-3-alkyl(aryl)-5-chloro- or 5-bromopyrazoles in preparative yields. The dichloroacrolein forms with alkylhydrazines and dimethylhydrazine only the corresponding hydrazones. Quantum-chemical calculations were performed characterizing the structure of the obtained ketones and dichloroacrolein C, alkylhydrazones, of dichloroacrolein dimethylhydrazone, of 1-alkyl-5-chloropyrazolinium halides, and 1-alkyl-5-chloropyrazoles.
• v. Auwers; Niemeyer, Journal fur praktische Chemie (Leipzig 1954), 1925, vol. <2> 110, p. 179
  作者：v. Auwers、Niemeyer

  DOI：——

  日期：——
• 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.