1-(2-nitrobenzyl)-2-(2-nitrophenyl)-1H-benzo[d]imidazole | 111796-43-1

• 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-nitrobenzyl)-2-(2-nitrophenyl)-1H-benzo[d]imidazole
• 英文别名: 2-(2-Nitrophenyl)-1-[(2-nitrophenyl)methyl]benzimidazole
• CAS: 111796-43-1
• 化学式: C₂₀H₁₄N₄O₄
• 分子量: 374.356
• InChiKey: GUAGBLGYTHNENO-UHFFFAOYSA-N

物化性质

• 熔点：
  120 °C
• 沸点：
  618.2±65.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  邻苯二胺 、 邻硝基苯甲醛 在 ammonium iron(III) sulfate 、 双氧水 作用下， 以 neat (no solvent) 为溶剂， 反应 0.33h， 以92%的产率得到1-(2-nitrobenzyl)-2-(2-nitrophenyl)-1H-benzo[d]imidazole
  参考文献：
  名称：

  无溶剂条件下硫酸铁铵（NH4Fe（SO4）2）催化合成2-芳基-1-芳基甲基-1H-1,3-苯并咪唑

  摘要：

  已发现NH 4 Fe（SO 4）2是在无溶剂条件下选择性合成2-芳基-1-芳基甲基-1 H -1,3-苯并咪唑类的温和有效催化剂。版权所有©2015 John Wiley＆Sons，Ltd.

  DOI：

  10.1002/aoc.3406

文献信息

• Natural Bio-surfactant for Pseudomulticomponent Synthesis of 2-Aryl-1- aryl Methyl-1H-benzimidazoles
  作者：Smita T. Morbale、Sachin K. Shinde、Shashikant A. Damate、Madhukar B. Deshmukh、Suresh S. Patil

  DOI：10.2174/1570178614666170710115331

  日期：2017.12.11

  Green chemistry emphasizes the development of environmentally benign chemical processes and technologies. Pseudo-multicomponent synthesis of 2-aryl-1-arylmethyl-1H-benzimidazoles using o-phenylenediamine and aromatic aldehydes is carried out by Bronsted acid type bio-surfactant as a catalyst. The green features of this method include the use of biodegradable catalyst obtained from renewable resource i.e. Citrus Limonium extract as bio-surfactant type Bronsted acid, which provides a micellar media for effective cyclocondensation. The critical micellar concentration (cmc) of biosurfactant was determined by conductivity method and visualized by light microscopy measurement. Identity of all pure compounds was ascertained on the basis of FT-IR, 1H NMR and 13C NMR spectroscopic techniques.

  绿色化学强调开发环保的化学过程和技术。采用邻苯二胺和芳香醛的伪多组分合成2-芳基-1-芳基甲基-1H-苯并咪唑是通过布朗斯特酸型生物表面活性剂作为催化剂进行的。这种方法的绿色特征包括使用来自可再生资源的生物可降解催化剂，即柠檬提取物，作为生物表面活性剂型布朗斯特酸，提供有效的微胶团介质用于环缩合反应。生物表面活性剂的临界胶束浓度（cmc）通过电导法确定，并通过光学显微镜测量进行可视化。所有纯化合物的身份通过FT-IR、1H NMR和13C NMR光谱技术得以确认。
• One-Pot Efficient Synthesis of 2-Aryl-1-arylmethyl-1<i>H</i>-benzimidazoles and 2,4,5-Triaryl-1<i>H</i>-imidazoles Using Oxalic Acid Catalyst
  作者：Nagnnath Kokare、Jaiprakash Sangshetti、Devanand Shinde

  DOI：10.1055/s-2007-983872

  日期：2007.9

  Oxalic acid was found to be a versatile catalyst for the synthesis of 2-aryl-1-arylmethyl-1H-benzimidazoles and 2-aryl-4,5-diphenyl-1H-imidazoles in moderate to excellent isolated yields. 2-Aryl-1-arylmethyl-1H-benzimidazoles were efficiently synthesized from o-phenylenediamine and various substituted aldehydes using 10 mol% oxalic acid. 2-Aryl-4,5-diphenyl-1H-imidazoles were synthesized from benzil or benzoin, ammonium acetate, and aromatic aldehydes. The advantages of this method are the use of an inexpensive and readily available catalyst, easy workup, and improved yields, and the use of an ethanol-water solvent that is considered to be relatively environmentally benign.

  草酸被发现是一种多功能催化剂，可用于合成2-芳基-1-芳基甲基-1H-苯并咪唑和2-芳基-4,5-二苯基-1H-咪唑，得到中等到优异的分离产率。2-芳基-1-芳基甲基-1H-苯并咪唑是通过使用10摩尔%的草酸，从邻苯二胺和各种取代醛高效合成的。2-芳基-4,5-二苯基-1H-咪唑则是从苯基和苯醇、醋酸铵以及芳香醛合成的。这种方法的优点在于使用了一种廉价且易得的催化剂，操作简便，产率提高，同时使用的乙醇-水溶剂被认为相对环保。
• Tosic Acid-on-Silica Gel: A Cheap and Eco-friendly Catalyst for a Convenient One-pot Synthesis of Substituted Benzimidazoles
  作者：Manas Chakrabarty、Ratna Mukherjee、Sulakshana Karmakar、Yoshihiro Harigaya

  DOI：10.1007/s00706-007-0714-2

  日期：2007.12

  2-Substituted and 1,2-disubstited benzimidazoles were prepared efficiently from o -phenylenediamines and aryl aldehydes using p -toluenesulphonic acid (5 mol%)-on-silica gel as a cheap and environmentally benign catalyst.

  使用 对 甲苯磺酸（5摩尔％）作为廉价廉价的环境友好型催化剂，由 邻 苯二胺和芳基醛 高效制备2-取代和1,2-二取代的苯并咪唑 。
• Cobalt manganese oxide nanoparticles as recyclable catalyst for efficient synthesis of 2-aryl-1-arylmethyl-1H-1,3-benzimidazoles under solvent-free conditions
  作者：Hossein Ahmadian、Hojat Veisi、Changiz Karami、Alireza Sedrpoushan、Maryam Nouri、Fariba Jamshidi、Iman Alavioon

  DOI：10.1002/aoc.3283

  日期：2015.5

  Cobalt manganese oxide nanocatalyst was synthesized and it was found that it is a highly efficient green catalyst for the synthesis of 2‐aryl‐1‐arylmethyl‐1H‐1,3‐benzimidazoles under solvent‐free conditions. The marked advantages of this method are the simple experimental procedures, shorter reaction times, high yields of product, reusable and non‐toxic catalyst and solvent‐free conditions. Copyright

  合成了氧化锰钴纳米催化剂，发现该催化剂是在无溶剂条件下合成2-芳基-1-芳基甲基-1H-1,3-苯并咪唑的高效绿色催化剂。该方法的显着优势是实验步骤简单，反应时间短，产物收率高，可重复使用且无毒的催化剂和无溶剂条件。版权所有©2015 John Wiley＆Sons，Ltd.
• Acetic acid-promoted condensation of o-phenylenediamine with aldehydes into 2-aryl-1-(arylmethyl)-1H-benzimidazoles under microwave irradiation
  作者：Davood Azarifar、Mojgan Pirhayati、Behrooz Maleki、Mehrangiz Sanginabadi、Nejat Yami

  DOI：10.2298/jsc090901096a

  日期：——

  An efficient and simple procedure was developed for the green synthesis of various 2-aryl-1-(arylmethyl)-1H-benzimidazoles in high yields by acetic acid-promoted condensation of o-phenylenediamine with aldehydes in air under microwave irradiation and transition metal catalystfree conditions.

  在微波辐照和无过渡金属催化剂条件下，通过乙酸促进邻苯二胺与醛在空气中的缩合，开发了一种高效、简单的绿色合成各种 2-芳基-1-（芳基甲基）-1H-苯并咪唑的方法，产率很高。