N-(4-chlorophenylmethylene)-2-methylthiobenzenamine | 142505-38-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: N-(4-chlorophenylmethylene)-2-methylthiobenzenamine
• 英文别名: 2-(methylthio)-N-(11-chlorobenzidine) aniline；2-methylthio-N-(4-chlorobenzylidene)aniline；MeS-C6H4-2-N=CH-C6H4-4-Cl；N-[(E)-(4-chlorophenyl)methylidene]-2-(methylsulfanyl)aniline；1-(4-chlorophenyl)-N-(2-methylsulfanylphenyl)methanimine
• CAS: 142505-38-2
• 化学式: C₁₄H₁₂ClNS
• 分子量: 261.775
• InChiKey: NNROVEASEJPKDS-UHFFFAOYSA-N

物化性质

• 熔点：
  92-94 °C
• 沸点：
  407.6±30.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  37.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(4-chlorophenylmethylene)-2-methylthiobenzenamine 在 过氧化二碳酸二异丙酯 、 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 15.0h， 生成 2-(4-氯苯基)苯并噻唑
  参考文献：
  名称：

  （2-亚烷基氨基苯基）硫化物与过氧二碳酸二异丙酯的反应：自由基与非自由基途径

  摘要：

  描述了2-甲硫基-或2-苯硫基芳嘌呤与过氧二碳酸二异丙酯（DPDC）的反应。苯硫基衍生物通过自由基机理环化成苯并噻唑，而甲硫基类似物也提供芳硫基甲基异丙基碳酸酯，以及苯并噻唑。最后的结果可以由非激进机构与激进机构并排运行的干预来解释。

  DOI：

  10.1016/s0040-4020(01)88475-1
• 作为产物：
  描述：

  4-氯苯甲醛 、 2-氨基茴香硫醚 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 5.0h， 以72%的产率得到N-(4-chlorophenylmethylene)-2-methylthiobenzenamine
  参考文献：
  名称：

  （2-亚烷基氨基苯基）硫化物与过氧二碳酸二异丙酯的反应：自由基与非自由基途径

  摘要：

  描述了2-甲硫基-或2-苯硫基芳嘌呤与过氧二碳酸二异丙酯（DPDC）的反应。苯硫基衍生物通过自由基机理环化成苯并噻唑，而甲硫基类似物也提供芳硫基甲基异丙基碳酸酯，以及苯并噻唑。最后的结果可以由非激进机构与激进机构并排运行的干预来解释。

  DOI：

  10.1016/s0040-4020(01)88475-1

文献信息

• Cyclopalladation of thio-substituted benzylideneanilines and their spectral characterization
  作者：F. Basuli、P. Chattopadhyay、C. Sinha

  DOI：10.1016/0277-5387(95)00504-8

  日期：1996.7

  Several 2-(alkylthio)-N-(benzylidene)anilines [XC6H4CHN C6H4 (2—SR), R−CH3 (1),−CH2Ph (2); XH (a), 4-CH3(b), 4-(OCH3) (c), 4-Cl (d) and 4-NO2 (e)] have been synthesized and reacted with Pd(OAc)2 in boiling benzene. The cyclopalladated acetato complexes (4/5) thus obtained react with LiCl, giving the chloro complexes with the coordination sphere Pd (C,N,S) Cl (6/7). The mode of ligand binding is

  几种2-（烷硫基）-N-（亚苄基）苯胺[XC 6 H 4 CH ＝ NC 6 H 4（2-SR），R 1 -CH 3（1），-CH 2 Ph（2）； n ＝ 1。合成了X aH（a），4-CH 3（b），4-（OCH 3）（c），4-Cl（d）和4-NO 2（e）]，并与Pd（OAc）反应2在沸腾的苯中。如此获得的环palpalated乙酰基络合物（4/5）与LiCl反应，得到的氯络合物与配位体Pd（C，N，S）Cl（6/7）。借助高分辨率的1 H NMR和IR数据确定了配体结合的模式。
• Synthesis and reactivity of new methylallylpalladium(II) complexes with bidentate 2-(methylthio-N-benzylidene)anilines
  作者：Raúl Contreras、Bárbara Loeb、Mauricio Valderrama、Mario Lagos、Francisco Burgos、Paola Ramı́rez、Javier Concepción

  DOI：10.1016/j.jorganchem.2003.10.028

  日期：2004.1

  This work describes the synthesis, characterisation and reactivity of new methylallyl Pd(II) complexes that contain bidentate 2-(methylthio-N-benzylidene)anilines as ligands. The reaction of the binuclear complex [(eta(3)-Me-allyl)Pd(mu-Cl)(2)] with AgBF4 causes the total abstraction of the chloride bridges, with the subsequent formation of an intermediary fragment of Pd(II). This fragment in turn reacts with neutral bidentate 2-(methylthio-N-benzylidene)anilines to give cationic complexes of Pd(II) of general formula [(eta(3)- Me-allyl)Pd(eta(2)-S,N-MeSC6H4N=CHC6H4(X)Y)]BF4 [X = H, Y = H (1); X = F, Y = H (2); X = Me, Y = H (3); X = H, Y = Cl (4); X = H, Y = Me2N (5); X = H, Y = NO, (6)]. The new complexes were characterised by means of elemental analysis, IR, NMR [H-1, F-19H-1}, C-13H-1}, P-31H-1}, Dept, H-1-H-1-COSY, HSQC HMBC] and mass spectroscopies. The reaction of the Pd(II) complexes with nucleophiles such as NaI, (EtO)(2)PS2K, KCN, KSCN or NaH lead to the deco-ordination of the bidentate ligands to give dimeric or polymeric complexes of Pd(II). The reactivity pattern observed is discussed by a theoretical analysis based on Fukui functions. (C) 2003 Elsevier B.V. All rights reserved.
• Bag; Sinha, Journal of the Indian Chemical Society, 1997, vol. 74, # 10, p. 763 - 764
  作者：Bag、Sinha

  DOI：——

  日期：——
• Synthesis, structure, and characterization of some ruthenium arene complexes of N-(arylmethylene)-2-(methylthio)anilines and 2-(methylthio)aniline
  作者：Christopher G. Hamaker、Dominic P. Halbach

  DOI：10.1016/j.ica.2005.06.017

  日期：2006.2

  A series of cationic, half-sandwich ruthenium complexes with the general formula [(eta(6)-p-cymene)RuCl(MeS-C6H4-2-N=CHAr)][PF6] (3a-h), have been prepared from the reaction of [(eta(6)-p-cymene)RuCl2](2) with various N,S-donor Schiff base ligands derived from 2-(methylthio)aniline and several substituted benzaldehydes. The related aniline complex [(eta(6)-p-cymene)RuCl(MeS-C6H4-2-NH2)][PF6] (4) was synthesized from 2-(methylthio)aniline. All of the ruthenium complexes were characterized by IR, H-1 NMR, and UV/Vis spectroscopies. The molecular structure of complex 4 was determined by X-ray crystallography. (c) 2005 Elsevier B.V. All rights reserved.