2-(1H-苯并咪唑-2-基甲基)-1H-苯并咪唑 | 5999-14-4

• 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-(1H-苯并咪唑-2-基甲基)-1H-苯并咪唑
• 英文名称: bis(1H-benzo[d]imidazol-2-yl)methane
• 英文别名: bis(benzimidazol-2-yl)methane；bis(1H-benzimidazol-2-yl)-methane；methylene-bis-2,2'-benzimidazole；2-(1H-Benzimidazol-2-ylmethyl)-1H-benzimidazole
• CAS: 5999-14-4
• 化学式: C₁₅H₁₂N₄
• mdl: MFCD00085631
• 分子量: 248.287
• InChiKey: VPJBLVPIUUNPLB-UHFFFAOYSA-N

物化性质

• 熔点：
  380-390 °C (decomp)
• 沸点：
  627.8±38.0 °C(Predicted)
• 密度：
  1.378±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.066
• 拓扑面积：
  57.4
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2-(1H-苯并咪唑-2-基甲基)-1H-苯并咪唑 在 hexafluorophosphoric acid 作用下， 以 水 为溶剂， 反应 0.08h， 以97%的产率得到
  参考文献：
  名称：

  Bis(benzimidazolium)methane salts: a potential guest for dibenzo-24-crown-8 towards [2]pseudorotaxanes

  摘要：

  We investigated the threading of bis(benzimidazolium) methane moieties with DB24C8 at 35 degrees C (room temperature) and found a high degree of association. The presence of threaded complexes was determined by H-1 NMR and also supported by high resolution mass spectrometry and B3LYP/6-31G**++calculations. A 2D NMR study was done to elucidate the host-guest geometry and the molecular interactions present. The variable temperature NMR experiment was done over a temperature range of 243-323 K. The threading was stable and visible even at 323 K. Acid-base equilibrium established the reversibility of the process. DFT optimized structures establish that two H-bonded links are present between O-1 center dot center dot center dot O-4', and O-3 center dot center dot center dot O-2', across the dibenzo axis of the crown. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.08.080
• 作为产物：
  描述：

  2,4-噁丁环二酮 、 邻苯二胺 在 polyphosphoric acid 作用下， 生成 2-(1H-苯并咪唑-2-基甲基)-1H-苯并咪唑
  参考文献：
  名称：

  Ti (IV) Complexes of Some Heterocyclic Ligands Synthesis, Characterization and Ethylene Polymerization Activity

  摘要：

  合成了31个双-（苯并咪唑、苯并噻唑和苯并恶唑）化合物与钛（IV）金属中心的配合物，进行了表征，并用甲基铝氧烷（MAO）激活，然后测试了其在催化乙烯聚合中的活性。各种催化剂的活性被发现与配体框架中的杂原子有关。39 / MAO获得了最高活性（573 kg PE / mol cat. h）。所产生的聚乙烯具有高分子量（最高可达1.5 × 10^6 g/mol）和宽的分子量分布（PD = 65）。这可能是由于MAO反离子与催化剂配体中的杂原子之间不同的相互作用生成了不同的活性位点。

  DOI：

  10.13005/ojc/320177

文献信息

• Expedient synthesis of benzimidazoles using amides
  作者：Pramod P. Kattimani、Ravindra R. Kamble、Gangadhar Y. Meti

  DOI：10.1039/c5ra00021a

  日期：——

  In the present report an efficient, rapid, facile and inexpensive route for the synthesis of benzimidazoles using 1,2-arylenediamines and amides in acidic medium under thermal/microwave conditions is developed.

  在本报告中，开发了一种高效、快速、简便且廉价的合成苯并咪唑的途径，该途径利用酸性介质下的热/微波条件使用1,2-芳二胺和酰胺进行合成。
• 2-Substituted Imidazole and Benzimidazole Corrosion Inhibitors
  申请人：Ecolab USA Inc.

  公开号：US20160348252A1

  公开（公告）日：2016-12-01

  Disclosed are methods of using nitrogen-containing compounds as corrosion inhibitors. The present method is used to inhibit corrosion of a metal surface in contact with an aqueous system using 2-substituted imidazoles and 2-substituted benzimidazoles, and provides enhanced protection against corrosion of metals in the aqueous system. The method comprises the use of corrosion inhibitors that are generally resistant to halogen attack and provide good corrosion resistance in the presence of oxidizing halogen-based biocides. Formulations comprising 2-substituted imidazoles and 2-substituted benzimidazoles are also disclosed.

  揭示了使用含氮化合物作为缓蚀剂的方法。本方法用于通过使用2-取代咪唑和2-取代苯并咪唑来抑制与水系接触的金属表面的腐蚀，并提供增强的金属在水系中的抗腐蚀保护。该方法包括使用通常对卤素攻击具有抵抗力并在存在氧化性卤素类生物杀菌剂时提供良好耐蚀性的缓蚀剂。还公开了包含2-取代咪唑和2-取代苯并咪唑的配方。
• Use of a ionic halide free copper catalyst for the production of dialkyl carbonates
  申请人：Stibrany T. Robert

  公开号：US20050054868A1

  公开（公告）日：2005-03-10

  A non-corrosive process for the preparation of dialkyl carbonate by reacting carbon monoxide, alkanol and an oxygen-containing gas in the presence of a ionic halogen free copper catalyst.

  在无卤化离子铜催化剂存在下，通过将一氧化碳、烷醇和含氧气体反应制备二烷基碳酸酯的无腐蚀过程。
• Bisbenzimidazole Derivatives as Potential Antimicrobial Agents: Design, Synthesis, Biological Evaluation and Pharmacophore Analysis
  作者：Ronak Haj Ersan、Kayhan Bolelli、Serpil Gonca、Aylin Dogen、Serdar Burmaoglu、Oztekin Algul

  DOI：10.1007/s11094-021-02389-x

  日期：2021.5

  In an attempt to design and synthesize a potent class of antimicrobials, 1,2-phenylenediamine derivatives were reacted with various aliphatic and heteroaliphatic dicarboxylic acids to generate a small library of 26 head-to-head bisbenzimidazole compounds (16 – 42) using the polyphosphoric acid method. These compounds were screened for their antibacterial activity and their antifungal activity. Compound 25 showed maximum potency against both Gram-positive and Gram-negative bacterial strains with minimum inhibitory concentration (MIC) values in the range of 7.81 – 31.25 μg/mL. In particular, it showed the maximum MIC values of 7.81 μg/mL against Gram-negative bacteria, which was four-fold more active than the standard drug ampicillin (MIC = 32.25 μg/mL). Compound 19 was found to be the most active against S. aureus with a MIC value of < 3.90 μg/mL, whereas the remaining compounds showed only low-to-moderate activity. Furthermore, all compounds exhibited low activity against all fungal strains in comparison to the standard drug fluconazole. I addition, pharmacophore hypotheses were generated to analyze structure–activity relationships between the molecular structures and antimicrobial activities on E. coli. This pharmacophore model can be useful in order to design new antimicrobial drugs. It can be suggested that the substitution of a phenyl ring at the 5/6 and 5′/6′ positions in symmetric bisbenzimidazole derivatives produces compounds with promising antimicrobial activity.

  为了设计并合成一类高效的抗菌药物，我们通过多磷酸法，将1,2-苯二胺衍生物与各种脂肪族和杂脂肪族二羧酸反应，生成了一个包含26个头对头双苯并咪唑化合物（16 – 42）的小型库。这些化合物经过筛选，评估了它们的抗菌活性和抗真菌活性。化合物25对革兰氏阳性和革兰氏阴性细菌株显示出最高的活性，其最低抑制浓度（MIC）值在7.81至31.25 μg/mL范围内。特别是，它对革兰氏阴性细菌显示出最高的MIC值7.81 μg/mL，比标准药物氨苄西林（MIC = 32.25 μg/mL）高出四倍。化合物19对金黄色葡萄球菌显示出最高的活性，其MIC值小于3.90 μg/mL，而其他化合物仅显示出低至中等的活性。此外，与标准药物氟康唑相比，所有化合物对所有真菌株均显示出低活性。此外，生成了药效团假设，以分析大肠杆菌上的分子结构与抗菌活性之间的结构-活性关系。这个药效团模型对于设计新的抗菌药物可能非常有用。可以建议，在对称双苯并咪唑衍生物的5/6和5′/6′位置上取代苯环会产生具有有前景的抗菌活性的化合物。
• Composition For the Vapor Phase Dehydrohalogenation of 1,1,2-Trihaloethane To 1,1-Dihaloethylene and Methods For Preparing and Using Such Composition
  申请人：Serhuchev Yurii Oleksiyovych

  公开号：US20080242902A1

  公开（公告）日：2008-10-02

  Described are compositions adapted to catalyze the vapor phase dehydrohalogenation of 1,1,2-trihaloethane to 1,1-dihaloethylene, e.g., 1,1,2-trichloroethane to vinylidene chloride. These materials include activated carbon and at least one benzimidazole-containing material defined herein as including benzimidazole, a derivative thereof, a salt thereof or mixtures thereof. Also described are methods for producing and using these catalytic compositions.

  描述了适用于催化1,1,2-三卤乙烷蒸汽相脱卤反应的组合物，例如1,1,2-三氯乙烷转化为二氯乙烯，例如，1,1,2-三氯乙烷转化为氯乙烯。这些材料包括活性炭和至少一种苯并咪唑含有物质，本文中定义为包括苯并咪唑、其衍生物、其盐或其混合物。还描述了制备和使用这些催化组合物的方法。