1-(2-thienylmethyl)-3-methylbenzimidazolium bromide | 1235552-04-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 1-(2-thienylmethyl)-3-methylbenzimidazolium bromide
• CAS: 1235552-04-1
• 化学式: Br*C₁₃H₁₃N₂S
• 分子量: 309.23
• InChiKey: NODSWKBTNUDOGY-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.42
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  8.81
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-(2-thienylmethyl)-3-methylbenzimidazolium bromide 、 palladium diacetate 、 丙酮 以 二甲基亚砜 为溶剂， 以50%的产率得到
  参考文献：
  名称：

  Synthesis, structural characterization and catalytic activity of a palladium(II) complex bearing a new ditopic thiophene-N-heterocyclic carbene ligand

  摘要：

  A new thiophene-functionalized benzimidazolium salt (2) has been prepared by reacting N-methylbenzimidazole with 2-bromomethylthiophene (1), which in turn was obtained by bromination of 2-thiophenemethanol with PBr3. Subsequent reaction of salt 2 with Pd(OAc)(2) afforded the cis-configured bis(carbene) Pd(II) complex (cis-3), which in solution exists as an inseparable mixture of cis-anti and cis-syn-rotamers in a 3.5:1 ratio. All new compounds have been fully characterized by spectroscopic and spectrometric methods. A preliminary catalytic study shows that cis-3 is highly active in the Suzuki-Miyaura coupling of aryl bromides with phenylboronic acid in/on water as environmentally benign reaction media. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2009.02.035
• 作为产物：
  描述：

  2-溴甲基噻吩 、 1-甲基苯并咪唑 以 甲苯 为溶剂， 以78%的产率得到1-(2-thienylmethyl)-3-methylbenzimidazolium bromide
  参考文献：
  名称：

  Synthesis, structural characterization and catalytic activity of a palladium(II) complex bearing a new ditopic thiophene-N-heterocyclic carbene ligand

  摘要：

  A new thiophene-functionalized benzimidazolium salt (2) has been prepared by reacting N-methylbenzimidazole with 2-bromomethylthiophene (1), which in turn was obtained by bromination of 2-thiophenemethanol with PBr3. Subsequent reaction of salt 2 with Pd(OAc)(2) afforded the cis-configured bis(carbene) Pd(II) complex (cis-3), which in solution exists as an inseparable mixture of cis-anti and cis-syn-rotamers in a 3.5:1 ratio. All new compounds have been fully characterized by spectroscopic and spectrometric methods. A preliminary catalytic study shows that cis-3 is highly active in the Suzuki-Miyaura coupling of aryl bromides with phenylboronic acid in/on water as environmentally benign reaction media. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2009.02.035