2-[3-Chloro-5-(trifluoromethyl)pyridin-2-yl]malononitrile | 338956-33-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-[3-Chloro-5-(trifluoromethyl)pyridin-2-yl]malononitrile
• 英文别名: 2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]propanedinitrile
• CAS: 338956-33-5
• 化学式: C₉H₃ClF₃N₃
• mdl: MFCD01315462
• 分子量: 245.591
• InChiKey: VTOFPCYTNQCBJU-UHFFFAOYSA-N

物化性质

• 熔点：
  210
• 沸点：
  290.0±35.0 °C(Predicted)
• 密度：
  1.488±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  60.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[3-Chloro-5-(trifluoromethyl)pyridin-2-yl]malononitrile 在 一水合肼 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 0.17h， 以33%的产率得到4-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-3,5-diamine
  参考文献：
  名称：

  A scalable approach to diaminopyrazoles using flow chemistry

  摘要：

  This Letter reports on how the combination of microwave and continuous flow chemistry facilitated the convenient preparation of aminopyrazoles from commercial aryl halides. The method was applied to a variety of substrates with good to excellent yields and further extended toward the complete flow synthesis of 5,7-dimethyl-3-phenylpyrazolo[1,5-a]pyrimidin-2-amine. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.05.152

文献信息

• Malononitrile: A Versatile d1-Synthon for the Synthesis of Hetero-aromatic Carboxylic Acid Derivatives
  作者：Marco Brünjes、Mark Ford、Hansjörg Dietrich、Kirsty Wilson

  DOI：10.1055/s-0034-1380572

  日期：——

  A convenient one-pot synthesis of heteroaromatic carboxylic acid derivatives from malononitrile substituted heteroaromatic compounds, namely pyridines, pyrimidines, and 1,3,5-triazines is described. In this procedure, the oxidation of malononitriles with anhydrous m-CPBA, followed by addition of different nucleophiles (alcohols, amines, thiols) under anhydrous conditions afforded the corresponding carboxylic acid derivatives in good to excellent yields.
• A scalable approach to diaminopyrazoles using flow chemistry
  作者：Noel S. Wilson、Augustine T. Osuma、Jennifer A.Van Camp、Xiangdong Xu

  DOI：10.1016/j.tetlet.2012.05.152

  日期：2012.8

  This Letter reports on how the combination of microwave and continuous flow chemistry facilitated the convenient preparation of aminopyrazoles from commercial aryl halides. The method was applied to a variety of substrates with good to excellent yields and further extended toward the complete flow synthesis of 5,7-dimethyl-3-phenylpyrazolo[1,5-a]pyrimidin-2-amine. (c) 2012 Elsevier Ltd. All rights reserved.