2-(2-溴苯基)-1-甲基苯并咪唑 | 92152-36-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 2-(2-溴苯基)-1-甲基苯并咪唑
• 中文别名: 1-甲基-2-邻溴苯基苯并咪唑
• 英文名称: 2-(2-bromophenyl)-1-methyl-1H-benzo[d]imidazole
• 英文别名: 2-(2-bromophenyl)-1-methylbenzimidazole
• CAS: 92152-36-8
• 化学式: C₁₄H₁₁BrN₂
• 分子量: 287.159
• InChiKey: GXKNXZLRJJKVDG-UHFFFAOYSA-N

物化性质

• 熔点：
  114-119°C
• 沸点：
  430.2±47.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• WGK Germany：
  3

SDS

MSDS英文版

反应信息

• 作为反应物：
  描述：

  2-(2-溴苯基)-1-甲基苯并咪唑 在 叔丁基锂 、 硼酸三异丙酯 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 3.5h， 以78%的产率得到N-methyl-2-(2-boronophenyl)benzimidazole
  参考文献：
  名称：

  [EN] BIFUNCTIONAL AMINO-BORON LEWIS ACID - LEWIS BASE CATALYST
  [FR] CATALYSEURS BIFONCTIONNELS

  摘要：

  公开号：

  WO2004113351A3
• 作为产物：
  描述：

  2-bromo-N'-(2-fluorophenyl)-N-methylbenzimidamide 在 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 16.0h， 以36%的产率得到2-(2-溴苯基)-1-甲基苯并咪唑
  参考文献：
  名称：

  Transition-Metal-Free Synthesis of Benzimidazoles Mediated by KOH/DMSO

  摘要：

  Benzimidazoles are prepared by intramolecular N-arylations of amidines mediated by potassium hydroxide in DMSO at 120 degrees C. In this manner, diversely substituted products have been obtained in moderate to very good yields.

  DOI：

  10.1021/ol403414v

文献信息

• Electrochemical Synthesis of Benzimidazoles via Dehydrogenative Cyclization of Amidines
  作者：Huai‐Bo Zhao、Jin‐Liang Zhuang、Hai‐Chao Xu

  DOI：10.1002/cssc.202100254

  日期：2021.4.9

  sustainable methodologies for the synthesis of N‐heterocycles is a constant focus of organic synthesis. Herein an electrochemical method is reported for the synthesis of benzimidazoles through dehydrogenative cyclization of easily available N‐aryl amidines. The reactions were conducted under simple constant current conditions in an undivided cell without need for catalysts, chemical oxidants, or additives, and

  N杂环合成的有效和可持续方法的发展一直是有机合成的重点。本文报道了一种电化学方法，用于通过易获得的N-芳基am的脱氢环化反应合成苯并咪唑。该反应是在简单的恒定电流条件下，在一个没有分隔的电池中进行的，不需要催化剂，化学氧化剂或添加剂，并且产生的H 2是唯一的理论副产物。
• An efficient palladium–benzimidazolyl phosphine complex for the Suzuki–Miyaura coupling of aryl mesylates: facile ligand synthesis and metal complex characterization
  作者：Kin Ho Chung、Chau Ming So、Shun Man Wong、Chi Him Luk、Zhongyuan Zhou、Chak Po Lau、Fuk Yee Kwong

  DOI：10.1039/c2cc15972d

  日期：——

  A new class of easily accessible hemilabile benzimidazolyl phosphine ligands has been developed. The ligand skeleton is prepared from commercially available and inexpensive o-phenylenediamine and 2-bromobenzoic acid. With catalyst loading down to 0.5 mol% palladium, excellent catalytic activity towards the Suzuki-Miyaura coupling of aryl mesylates is still observed. This represents the lowest catalyst

  已经开发出一种新型的易于获得的半不稳定的苯并咪唑基膦配体。配体骨架由可商购的和廉价的邻苯二胺和2-溴苯甲酸制备。在催化剂负载量低至0.5mol％钯的情况下，仍观察到对甲磺酸甲磺酸酯的Suzuki-Miyaura偶联的优异催化活性。通常，这代表了迄今为止该反应所达到的最低催化剂负载量。X射线晶体学表明，新的配体L2以Kappa（2）-P，N的方式与Pd配合。
• Buchwald-Hartwig Amination of Aryl Chlorides Catalyzed by Easily Accessible Benzimidazolyl Phosphine-Pd Complexes
  作者：Chau So、Fuk Kwong、Kin Chung、Shun Wong、Chi Luk、Zhongyuan Zhou、Chak Lau

  DOI：10.1055/s-0031-1290666

  日期：2012.5

  This study describes the efficacy of benzimidazolyl phosphine ligands, which are easily synthesized from inexpensive and commercially available o-phenylenediamine, 2-bormobenzoic acid, and chlorophosphines, in the Buchwald-Hartwig amination of aryl chlorides. Primary and secondary aromatic/aliphatic amines are effective substrates in this catalytic system. Functional groups such as keto and esters are also compatible. The catalyst loading can be reduced to 0.1 mol% Pd.

  本研究描述了从廉价且市售的邻苯二胺、2-溴苯甲酸和氯膦化合物容易合成的苯并咪唭基膦配体在Buchwald-Hartwig芳基氯化物胺化反应中的效能。在该催化体系中，伯和仲芳香/脂肪胺是有效的底物。酮和酯等功能团也能兼容。催化剂负载量可降至0.1 mol% Pd。
• P,N-Type benzimidazolyl phosphine ligands for the palladium-catalyzed Suzuki coupling of potassium aryltrifluoroborates and aryl chlorides
  作者：Shun Man Wong、Chau Ming So、Kin Ho Chung、Chi Him Luk、Chak Po Lau、Fuk Yee Kwong

  DOI：10.1016/j.tetlet.2012.05.017

  日期：2012.7

  describes the efficacy of P,N-type benzimidazolyl phosphine ligands, which can be easily synthesized from commercially available and inexpensive starting materials. The application of this ligand array in palladium-catalyzed Suzuki–Miyaura coupling reaction of aryl chlorides with potassium aryltrifluoroborates is described. The air stable benzimidazolyl phosphines in combination with a palladium metal precursor

  这项研究描述了P，N型苯并咪唑基膦配体的功效，该配体可以很容易地从市售和廉价的原料中合成。描述了这种配体阵列在钯催化的芳基氯与芳基三氟硼酸钾的Suzuki-Miyaura偶联反应中的应用。空气稳定的苯并咪唑基膦与钯金属前体的结合为未活化的芳基氯的Suzuki-Miyaura偶联提供了高效的催化剂，催化剂负载量仅为0.05 mol％。
• Copper-catalyzed C-C coupling and cyclization: Synthesis of benzo[4,5]imidazo[1,2-a]pyridines and benzo[4,5]imidazo[2,1-a]isoquinolines
  作者：Byeong Woo Yang、Pham Duy Quang Dao、Nam Sik Yoon、Chan Sik Cho

  DOI：10.1016/j.jorganchem.2017.09.025

  日期：2017.11

  3-diketones in DMF in the presence of a catalytic amount of copper(I) iodide and a base to afford the corresponding benzo[4,5]imidazo[1,2-a]pyridines in moderate yields. 2-(2-Bromoaryl)benzimidazoles also react with 1,3-diketones under similar reaction conditions to give benzo[4,5]imidazo[2,1-a]isoquinolines in similar yields.

  在催化量的碘化铜（I）和碱存在下，将2-（2-溴乙烯基）苯并咪唑与1,3-二酮在DMF中偶联并环化，得到相应的苯并[4,5]咪唑[1， 2- α ]吡啶的产率中等。2-（2-溴芳基）苯并咪唑还可以在相似的反应条件下与1,3-二酮反应，以相似的产率得到苯并[4,5]咪唑并[2,1- a ]异喹啉。