1-(2,4,6-trimethylbenzyl)-2-(2'-pyridyl)benzimidazole | 1245631-71-3

• 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-(2,4,6-trimethylbenzyl)-2-(2'-pyridyl)benzimidazole
• 英文别名: 1-(2,4,6-Trimethylbenzyl)-2-(20-pyridyl)benzimidazole；2-pyridin-2-yl-1-[(2,4,6-trimethylphenyl)methyl]benzimidazole
• CAS: 1245631-71-3
• 化学式: C₂₂H₂₁N₃
• 分子量: 327.429
• InChiKey: FACPHHOXVGMGDF-UHFFFAOYSA-N

物化性质

• 熔点：
  170-172 °C
• 沸点：
  546.5±52.0 °C(predicted)
• 密度：
  1.12±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  双(乙腈)氯化钯(II) 、 1-(2,4,6-trimethylbenzyl)-2-(2'-pyridyl)benzimidazole 以 四氢呋喃 为溶剂， 反应 2.0h， 以79%的产率得到
  参考文献：
  名称：

  Substituted 2-(2''-pyridyl)benzimidazole palladium(II) complexes as an efficient catalytic system for Suzuki--Miyaura cross-coupling reactions

  摘要：

  制备了一系列新型$N,N$型2-(2'-吡啶基)苯并咪唑配体(2A$_{\mathbf{1}}$、2A$_{\mathbf{2}}$、3B$_{\mathbf{1}}$、3B$_{\mathbf{2}}$、3B$_{\mathbf{3}}$和4C$_{\mathbf{1}}$)及其Pd(II)配合物(5A$_{\mathbf{1}}$、5A$_{\mathbf{2}}$、6B$_{\mathbf{1}}$、6B$_{\mathbf{2}}$、6B$_{\mathbf{3}}$和7C$_{\mathbf{1}}$)，并通过常规光谱方法和元素分析进行了表征。含有$N$配位的苯并咪唑配体使得钯催化剂在Suzuki-Miyaura偶联反应中展现出极高的催化活性。在确定具有甲基苯并咪唑环结构的5A$_{\mathbf{1}}$为最佳活性催化剂后，通过改变底物、碱、时间、气氛和水等因素进行了优化研究。发现使用DMF:H$_{2}$O (4/1)溶剂和Cs$_{2}$CO$_{3}$作为碱对反应产率（100%）的提高至关重要。

  DOI：

  10.3906/kim-1505-105
• 作为产物：
  描述：

  2-(2-吡啶)-苯并咪唑 、 2,4,6-三甲基溴化苄 在 potassium hydroxide 作用下， 以 甲苯 为溶剂， 反应 30.0h， 以85%的产率得到1-(2,4,6-trimethylbenzyl)-2-(2'-pyridyl)benzimidazole
  参考文献：
  名称：

  Substituted 2-(2''-pyridyl)benzimidazole palladium(II) complexes as an efficient catalytic system for Suzuki--Miyaura cross-coupling reactions

  摘要：

  制备了一系列新型$N,N$型2-(2'-吡啶基)苯并咪唑配体(2A$_{\mathbf{1}}$、2A$_{\mathbf{2}}$、3B$_{\mathbf{1}}$、3B$_{\mathbf{2}}$、3B$_{\mathbf{3}}$和4C$_{\mathbf{1}}$)及其Pd(II)配合物(5A$_{\mathbf{1}}$、5A$_{\mathbf{2}}$、6B$_{\mathbf{1}}$、6B$_{\mathbf{2}}$、6B$_{\mathbf{3}}$和7C$_{\mathbf{1}}$)，并通过常规光谱方法和元素分析进行了表征。含有$N$配位的苯并咪唑配体使得钯催化剂在Suzuki-Miyaura偶联反应中展现出极高的催化活性。在确定具有甲基苯并咪唑环结构的5A$_{\mathbf{1}}$为最佳活性催化剂后，通过改变底物、碱、时间、气氛和水等因素进行了优化研究。发现使用DMF:H$_{2}$O (4/1)溶剂和Cs$_{2}$CO$_{3}$作为碱对反应产率（100%）的提高至关重要。

  DOI：

  10.3906/kim-1505-105

文献信息

• The synthesis and characterization of 2-(2′-pyridyl)benzimidazole heteroleptic ruthenium complex: Efficient sensitizer for molecular photovoltaics
  作者：Cigdem Sahin、Mahmut Ulusoy、Ceylan Zafer、Cihan Ozsoy、Canan Varlikli、Thomas Dittrich、Bekir Cetinkaya、Siddik Icli

  DOI：10.1016/j.dyepig.2009.06.016

  日期：2010.1

  The novel ligand 1-(2,4,6-trimethylbenzyl)-2-(2'-pyridyl)benzimidazole and its heteroleptic ruthenium (II) complex were synthesized. The complex was characterized using spectroscopic methods and cyclic voltammetry. Charge-separation was investigated within nanoporous titanium dioxide employing surface photovoltage spectroscopy. The performance of the ruthenium complex as a charge transfer photosensitizer in nanocrystalline, titanium dioxide-based, dye sensitized solar cells was studied under standard AM 1.5 sunlight using an electrolyte consisting of 0.6 M1-butyl-3-methyl-imidazolium iodide, 0.1 M lithium iodide, 0.05 M iodine and 0.5 M 4-tert-butyl pyridine in 3-methoxy propyonitrile. The novel complex had a photocurrent density of 9.47 mA cm(-2), 600 mV open circuit potential and 0.60 fill factor yielding an efficiency of 3.4%. The photovoltaic performance of the colorant was compared with that of cis-bis(isothiocyanato)(2,2'-bipyridyl-4,4'-dicarboxylato) (2,2'-bipyridyl-4,4'-di-nonyl) ruthenium(II): both compounds exhibited similar efficiency, while the fill factor value was higher for the novel dye. (C) 2009 Elsevier Ltd. All rights reserved.
• Substituted 2-(2''-pyridyl)benzimidazole palladium(II) complexes as an efficient catalytic system for Suzuki--Miyaura cross-coupling reactions
  作者：Mahmut ULUSOY、Nurdal ÖNCEL、Emine AYTAR

  DOI：10.3906/kim-1505-105

  日期：——

  A new series of $N,N$-type 2-(2'-pyridyl)benzimidazole ligands (2A$_\mathbf1}}$, 2A$_\mathbf2}}$, 3B$_\mathbf1}}$, 3B$_\mathbf2}}$, 3B$_\mathbf3}}$, and 4C$_\mathbf1}})$ and their Pd(II) complexes (5A$_\mathbf1}}$, 5A$_\mathbf2}}$, 6B$_\mathbf1}}$, 6B$_\mathbf2}}$, 6B$_\mathbf3}}$, and 7C$_\mathbf1}})$ were prepared and characterized by conventional spectroscopic methods and elemental analyses. The incorporation of $N$-coordinated benzimidazole complexes of palladium gave high catalytic activity in the Suzuki-Miyaura coupling of aryl halides substrates. After determining the best active catalyst as 5A$_\mathbf1}}$, bearing the mesityl substituent on the benzimidazole ring with the Pd(II) ion, optimization studies were carried out via changing the substrate, base, time, atmosphere, and the effect of water. The DMF:H$_2}$O (4/1) and Cs$_2}$CO$_3}$ as base were found to be critical for the efficiency of the reaction yield (100%).

  制备了一系列新型$N,N$型2-(2'-吡啶基)苯并咪唑配体(2A$_\mathbf1}}$、2A$_\mathbf2}}$、3B$_\mathbf1}}$、3B$_\mathbf2}}$、3B$_\mathbf3}}$和4C$_\mathbf1}}$)及其Pd(II)配合物(5A$_\mathbf1}}$、5A$_\mathbf2}}$、6B$_\mathbf1}}$、6B$_\mathbf2}}$、6B$_\mathbf3}}$和7C$_\mathbf1}}$)，并通过常规光谱方法和元素分析进行了表征。含有$N$配位的苯并咪唑配体使得钯催化剂在Suzuki-Miyaura偶联反应中展现出极高的催化活性。在确定具有甲基苯并咪唑环结构的5A$_\mathbf1}}$为最佳活性催化剂后，通过改变底物、碱、时间、气氛和水等因素进行了优化研究。发现使用DMF:H$_2}$O (4/1)溶剂和Cs$_2}$CO$_3}$作为碱对反应产率（100%）的提高至关重要。