3-chloro-2-mercaptobenzonitrile | 38244-28-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚类
• 英文名称: 3-chloro-2-mercaptobenzonitrile
• 英文别名: 3-chloro-2-sulfanylbenzonitrile
• CAS: 38244-28-9
• 化学式: C₇H₄ClNS
• 分子量: 169.634
• InChiKey: XUBDWZBNGLESRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  24.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-氯-2-氟苯腈 在 sodium sulfide 、 盐酸 、 锌 作用下， 以 N,N-二甲基甲酰胺 、 水 为溶剂， 反应 1.0h， 以86%的产率得到3-chloro-2-mercaptobenzonitrile
  参考文献：
  名称：

  About the reaction of aryl fluorides with sodium sulfide: investigation into the selectivity of substitution of fluorobenzonitriles to yield mercaptobenzonitriles via SNAr displacement of fluorine

  摘要：

  In this report we describe a simple synthesis of mercaptobenzonitriles from the reaction of fluorobenzonitriles with Na2S in DMF at room temperature and following direct treatment with Zn/HCl. Significantly, 2- and 4-fluorobenzonitriles substituted with chlorine or bromine, from the reaction of but not iodine, undergo selective substitution of fluorine at room temperature to yield synthetically useful halo-substituted mercaptobenzonitriles. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.03.032

文献信息

• MARKERT J.; HAGEN H., LIEBIGS ANN. CHEM., 1980, NO 5, 768-778
  作者：MARKERT J.、 HAGEN H.

  DOI：——

  日期：——
• About the reaction of aryl fluorides with sodium sulfide: investigation into the selectivity of substitution of fluorobenzonitriles to yield mercaptobenzonitriles via SNAr displacement of fluorine
  作者：Tony Taldone、Pallav D. Patel、Hardik J. Patel、Gabriela Chiosis

  DOI：10.1016/j.tetlet.2012.03.032

  日期：2012.5

  In this report we describe a simple synthesis of mercaptobenzonitriles from the reaction of fluorobenzonitriles with Na2S in DMF at room temperature and following direct treatment with Zn/HCl. Significantly, 2- and 4-fluorobenzonitriles substituted with chlorine or bromine, from the reaction of but not iodine, undergo selective substitution of fluorine at room temperature to yield synthetically useful halo-substituted mercaptobenzonitriles. (C) 2012 Elsevier Ltd. All rights reserved.