2-[(2-chlorophenyl)amino]benzonitrile | 18201-84-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[(2-chlorophenyl)amino]benzonitrile
• 英文别名: N-(2-Chlorphenyl)-anthranilsaeurenitril；2-(2-Chloroanilino)benzonitrile
• CAS: 18201-84-8
• 化学式: C₁₃H₉ClN₂
• mdl: MFCD11119109
• 分子量: 228.681
• InChiKey: CXTJIRJZZGIWTC-UHFFFAOYSA-N

物化性质

• 沸点：
  356.8±27.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  35.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[(2-chlorophenyl)amino]benzonitrile 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 六甲基二硅烷 、 三(4-三氟甲苯基)膦 作用下， 以 乙基环己烷 为溶剂， 反应 15.0h， 以55%的产率得到咔唑
  参考文献：
  名称：

  Rhodium-Catalyzed Silylation and Intramolecular Arylation of Nitriles via the Silicon-Assisted Cleavage of Carbon−Cyano Bonds

  摘要：

  A rhodium-catalyzed silylation reaction of carbon-cyano bonds using disilane has been developed. Under these catalytic conditions, carbon-cyano bonds in aryl, alkenyl, allyl, and benzyl cyanides bearing a variety of functional groups can be silylated. The observation of an enamine side product in the silylation of benzyl cyanides and related stoichiometric studies indicate that the carbon-cyano bond cleavage proceeds through the deinsertion of silyl isocyanide from eta(2)-iminoacyl complex B. Knowledge gained from these studies has led to the development of a new intramolecular biaryl coupling reaction in which aryl cyanides and aryl chlorides are cross-coupled.

  DOI：

  10.1021/ja804992n
• 作为产物：
  描述：

  2-溴苯甲酸钠 在 calcium hydride 、 二乙二醇二甲醚 、 三乙胺 、 copper(ll) bromide 、 三氯氧磷 作用下， 生成 2-[(2-chlorophenyl)amino]benzonitrile
  参考文献：
  名称：

  一些5-（2-苯胺基苯基）四唑的制备和抗炎特性。

  摘要：

  DOI：

  10.1021/jm00307a025

文献信息

• Aminocyanation by the Addition of N–CN Bonds to Arynes: Chemoselective Synthesis of 1,2-Bifunctional Aminobenzonitriles
  作者：Bin Rao、Xiaoming Zeng

  DOI：10.1021/ol403346x

  日期：2014.1.3

  An efficient aminocyanation by the direct addition of aryl cyanamides to arynes is described, enabling incorporation of highly useful amino and cyano groups synchronously via cleavage of inert N-CN bonds, affording synthetically useful 1,2-bifunctional aminobenzonitriles. The postsynthetic functionalization of the aminocyanation products allows diverse formation of synthetically important derivatives such as drug molecule Ponstan and fused heterocycles.
• Preparation and antiinflammatory properties of some 5-(2-anilinophenyl)tetrazoles
  作者：Peter F. Juby、T. W. Hudyma、Morton Brown

  DOI：10.1021/jm00307a025

  日期：1968.1
• Rhodium-Catalyzed Silylation and Intramolecular Arylation of Nitriles via the Silicon-Assisted Cleavage of Carbon−Cyano Bonds
  作者：Mamoru Tobisu、Yusuke Kita、Yusuke Ano、Naoto Chatani

  DOI：10.1021/ja804992n

  日期：2008.11.26

  A rhodium-catalyzed silylation reaction of carbon-cyano bonds using disilane has been developed. Under these catalytic conditions, carbon-cyano bonds in aryl, alkenyl, allyl, and benzyl cyanides bearing a variety of functional groups can be silylated. The observation of an enamine side product in the silylation of benzyl cyanides and related stoichiometric studies indicate that the carbon-cyano bond cleavage proceeds through the deinsertion of silyl isocyanide from eta(2)-iminoacyl complex B. Knowledge gained from these studies has led to the development of a new intramolecular biaryl coupling reaction in which aryl cyanides and aryl chlorides are cross-coupled.