2-(4-bromo-phenylazo)-1H-imidazole | 93937-76-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(4-bromo-phenylazo)-1H-imidazole
• 英文别名: 2-(4-bromo-phenylazo)-1H-imidazole；2-(4-Brom-phenylazo)-1H-imidazol；2-(p-Bromphenylazo)-imidazol；2(p-Bromphenylazo)imidazol
• CAS: 93937-76-9
• 化学式: C₉H₇BrN₄
• 分子量: 251.085
• InChiKey: FPGIMTCCIRKDRM-BUHFOSPRSA-N

物化性质

• 沸点：
  406.6±47.0 °C(Predicted)
• 密度：
  1.65±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  53.4
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(4-bromo-phenylazo)-1H-imidazole 、 cadmium(II) nitrate 以 甲醇 为溶剂， 以85%的产率得到[Cd(BrC6H4NNC3H3N2)2(nitrate)2]
  参考文献：
  名称：

  Aryl azo imidazole assisted self-assembly of d10 metal complexes: Influence of halogen substitution and counter ions

  摘要：

  A series of eight coordination networks has been obtained by the self-assembly of the aryl azo imidazole based building block and with d(10) metal [Zn(II), Cd(II), and Hg(II)] and counter anion (Cl-, NO3-, SCN-) in order to rationalize the effect of coordination behavior of the metal ion, the size of the anions and the substitution effects of ligands upon the structure adopted by these metal complexes. Influences of halogen (Cl-, Br-, and I-) substitutions are reflected in the precise molecular level architecture in the individual complexes. The parameters related to the coordination sphere depend on the metal-to-ligand ratios and are also influenced by the solvent of crystallization. A competition between the coordinating capabilities of the counter anion with ligands and its shape led to neutral and anionic metal complexes. Furthermore, various physicochemical studies viz, thermal behaviors, absorption spectra have been conducted to rationalize their structure in solution phase. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2010.08.004
• 作为产物：
  描述：

  咪唑 、 (4-bromophenyl)diazonium chloride 生成 2-(4-bromo-phenylazo)-1H-imidazole
  参考文献：
  名称：

  MACIEJEWSKA D.; SKULSKI L., BULL. ACAD. POL. SCI. SER. SCI. CHIM., 1979, 27, NO 4, 249-255

  摘要：

  DOI：

文献信息

• Syntheses of Symmetric and Unsymmetric Bis-imidazole Derivatives Using Phase-Transfer Catalysis
  作者：Kun-Peng Zhang、Tian-Qi Jin、Jun-Qiang Zhou、Ting-Ting Ma、Chuan-Ming Jin

  DOI：10.1002/jhet.2917

  日期：2017.11

  unsymmetric bisimidazole derivatives was established. The symmetric bisimidazolylmethane derivatives 1a–9a was prepared with 2‐substituted imidazole derivatives 1–9 as reaction materials. However, the symmetric and unsymmetric bisimidazolylmethane derivatives 10a–12a and 10b–12b was obtained, respectively. With 4‐position with the azo‐groups imidazole derivatives 10–12 were used as reaction materials

  建立了制备对称和不对称联咪唑衍生物的简便方法。对称的双咪唑基甲烷衍生物1a–9a是使用2-取代的咪唑衍生物1–9作为反应材料制备的。但是，分别获得了对称和不对称的双咪唑基甲烷衍生物10a-12a和10b-12b。具有偶氮基团的4位咪唑衍生物10-12被用作反应材料。所有这些化合物均已通过NMR，ESI-MS和EA在结构上进行了表征。和图8A和12A中的特征还在于X射线单晶扩散。
• Photoisomerization of 2-Arylazoimidazoles under Visible Light: Identifying a Predictive Tool to Anticipate and Tune Likely Photoswitching Performance and Cis Half-Life
  作者：Anirban Dolai、Sk Majid Box、Supriya Bhunia、Satyajit Bera、Arpan Das、Subhas Samanta

  DOI：10.1021/acs.joc.3c00211

  日期：2023.7.7

  aryl-substituted N-methyl-2-arylazoimidazoles were synthesized, and their photoswitching performances and cis–trans isomerization kinetics were thoroughly investigated experimentally and theoretically. Para-π-donor-substituted azoimidazoles with highly twisted T-shaped cis conformations showed nearly complete bidirectional photoswitching, whereas di-o-substituted switches exhibited very long cis half-lives

  偶氮吡唑是一类新兴的光开关，而类似的基于偶氮咪唑的开关由于其顺式半衰期短、顺反光回复产率差以及有毒的紫外线（UV）光辅助异构化而无法引起太多关注。合成了一系列 24 种芳基取代的N-甲基-2-芳基偶氮咪唑，并从实验和理论上深入研究了它们的光开关性能和顺反异构化动力学。对位-π-供体取代的偶氮咪唑具有高度扭曲的T形顺式构象，显示出几乎完全的双向光开关，而二-o-取代的开关表现出非常长的顺式半衰期（天-年），具有近乎理想的 T 形构象。这项研究展示了芳环中的电子密度如何通过扭转 NNAr 二面角来影响顺式半衰期和顺反光复归，这可以用作预测指标，用于设想和调整任何可能的开关性能和半衰期。给予2-芳基偶氮咪唑。通过应用该工具，设计了两种性能更好的偶氮咪唑光电开关。所有开关均允许紫光（400-405 nm）和橙光（>585 nm）照射分别进行正向和反向异构化，并表现出相对较高的量子产率和令人印象深刻的抗光漂白性。
• Fargher; Pyman, Journal of the Chemical Society, 1919, vol. 115, p. 250
  作者：Fargher、Pyman

  DOI：——

  日期：——
• Salwinska, Ewa; Suwinski, Jerzy, Polish Journal of Chemistry, 1981, vol. 55, # 7/8, p. 1677 - 1679
  作者：Salwinska, Ewa、Suwinski, Jerzy

  DOI：——

  日期：——