2-(2'-hydroxy-4-methylphenylazo)-1-methylbenzimidazole | 65446-32-4

• 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: 2-(2'-hydroxy-4-methylphenylazo)-1-methylbenzimidazole
• 英文别名: 2-(2-Hydroxy-5-methylphenylazo)-1-methylbenzimidazole；2-[(1-methyl-2-benzimidazolyl)azo]-p-cresol；Phenol, 4-methyl-2-[(1-methyl-1H-benzimidazol-2-yl)azo]-；4-methyl-2-[(1-methylbenzimidazol-2-yl)diazenyl]phenol
• CAS: 65446-32-4
• 化学式: C₁₅H₁₄N₄O
• 分子量: 266.302
• InChiKey: FPTAILLTZVMOBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  62.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  palladium diacetate 、 2-(2'-hydroxy-4-methylphenylazo)-1-methylbenzimidazole 以 丙酮 为溶剂， 生成
  参考文献：
  名称：

  Garnovskii; Burlov; Antsyshkina, Russian Journal of Inorganic Chemistry, 1996, vol. 41, # 1, p. 85 - 91

  摘要：

  DOI：
• 作为产物：
  描述：

  邻氨基对甲苯酚 在 盐酸 、 sodium hydride 、 sodium nitrite 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 2-(2'-hydroxy-4-methylphenylazo)-1-methylbenzimidazole
  参考文献：
  名称：

  Benzimidazole based ratiometric and colourimetric chemosensor for Ni(II)

  摘要：

  A highly sensitive and selective benzimidazole based colourimetric chemosensor (HL) for the efficient detection of Ni2+ has been reported. The synthesized chemosensor HL is highly efficient in detecting Ni2+ over other metal ions that commonly coexist with Ni2+ in physiological and environmental samples. HL also shows distinct color change from orange yellow to blue visible under the naked eye due to specific binding with Ni2+. This color change corresponds to a large red shift of the UV-Vis spectrum from 403 nm to 600 nm with a distinct isosbestic point at around 500 nm. The cation sensing property of the receptor HL has been examined by UV-Vis spectroscopy. Electronic structure of the HL-Ni2+ complex and sensing mechanism has been interpreted by DFT and TDDFT calculations. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2015.08.052

文献信息

• Direct chemical and electrochemical syntheses of coordination compounds of benzazolyl azo ligands
  作者：Anatolii S. Burlov、Alla S. Antsyshkina、Georgii G. Sadikov、Yurii V. Koshchienko、Ludmila N. Divaeva、Sergei A. Mashchenko、Ali I. Uraev、Dmitrii A. Garnovskii、Igor S. Vasilchenko、Valery G. Vlasenko、Yan V. Zubavichus、Gennadii S. Borodkin、Boris I. Kharisov、Tomás C. Hernández García、Vladimir S. Sergienko、Alexander D. Garnovskii

  DOI：10.1080/00958971003690421

  日期：2010.3.20

  crystal diffraction data revealed the existence of octahedral nickel, zinc, and cadmium complexes containing four five-membered metallocycles with the N4О2 or N6 ligand environments. The formation of five-membered coordination units, non-typical for azo ligands, is explained on the basis of inner-chelate competitive metal binding of ambidentate ligand systems.

  2-羟基（氨基苯基萘基）-偶氮-1-烷基苯并咪唑的螯合物通过电化学（零价d-金属的阳极溶解）和化学（来自相同金属的乙酸盐）在甲醇中合成获得。EXAFS 和 X 射线单晶衍射数据揭示了八面体镍、锌和镉配合物的存在，该配合物含有四个五元金属环，具有 N4О2 或 N6 配体环境。偶氮配体的非典型五元配位单元的形成是基于双齿配体系统的内螯合竞争性金属结合来解释的。
• Diazo compounds of the heterocyclic series. 4. Some peculiarities of the diazo coupling of benzimidazole-2-diazonium salts with phenols and their ethers
  作者：S. N. Kolodyazhnaya、L. N. Divaeva、R. A. Sogomonova、A. M. Simonov

  DOI：10.1007/bf00487430

  日期：1990.5
• Synthesis, crystal structure and spectral properties of 2-[(1-Methyl-2-benzimidazolyl)azo]-p-cresol: An experimental and theoretical study
  作者：Deblina Sarkar、Ajoy Kumar Pramanik、Tapan Kumar Mondal

  DOI：10.1016/j.saa.2013.06.049

  日期：2013.11

  2-[(1-Methyl-2-benzimidazolyl)azo]-p-cresol (HL), containing phenolic-OH function and benzimidazole moiety has been synthesized and characterized. The chemical, electronic structure and photophysical properties have been studied by spectroscopic analysis abetted with DFT and TDDFT calculations. The change in electronic spectra of HL by titration with aq. NaOH is studied and well supported by TDDFT calculations. The structure is confirmed by single crystal X-ray study. In the unit cell, two HL molecules are H-bonded with H2O molecule and forms dimmeric structure. The molecule forms 2D-supramolecular structure by inter-molecular H-bonding and pi-pi interactions. (C) 2013 Elsevier B.V. All rights reserved.