3,4,5-tribromo-1,2-diaminobenzene | 500862-66-8

• 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: 3,4,5-tribromo-1,2-diaminobenzene
• 英文别名: 3,4,5-tribromo-o-phenylenediamine；3,4,5-Tribrom-o-phenylendiamin；3.4.5-Tribrom-phenylendiamin-(1.2)；3.4.5-Tribrom-1.2-diamino-benzol；3,4,5-Tribromobenzene-1,2-diamine
• CAS: 500862-66-8
• 化学式: C₆H₅Br₃N₂
• 分子量: 344.831
• InChiKey: GDIXPBNAUWBTOO-UHFFFAOYSA-N

物化性质

• 沸点：
  357.7±37.0 °C(Predicted)
• 密度：
  2.419±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,4,5-tribromo-1,2-diaminobenzene 在 sodium nitrite 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 1.0h， 以83%的产率得到4,5,6-tribromobenzotriazole
  参考文献：
  名称：

  Synthesis and Physico-Chemical Properties in Aqueous Medium of All Possible Isomeric Bromo Analogues of Benzo-1H-Triazole, Potential Inhibitors of Protein Kinases

  摘要：

  In ongoing studies on the role of the individual bromine atoms of 4,5,6,7-tetrabromobenzotriazole (TBBt) in its relatively selective inhibition of protein kinase CK2 alpha, we have prepared all the possible two mono-, four di-, and two tri-bromobenzotriazoles and determined their physicochemical properties in aqueous medium. They exhibited a general trend of a decrease in solubility with an increase in the number of bromines on the benzene ring, significantly modulated by the pattern of substitution. For a given number of attached bromines, this was directly related to the electronic effects resulting from different sites of substitution, leading to marked variations of pK(a) values for dissociation of the triazole proton. Experimental data (pK(a), solubility) and ab initio calculations demonstrated that hydration of halogenated benzotriazoles is driven by a subtle balance of hydrophobic and polar interactions. The combination of QM-derived free energies for solvation and proton dissociations was found to be a reasonably good predictor of inhibitory activity of halogenated benzotriazoles vs CK2 alpha. Since the pattern of halogenation of the benzene ring of benzotriazole has also been shown to be one of the determinants of inhibitory potency vs some viruses and viral enzymes, the present comprehensive description of their physicochemical properties should prove helpful in efforts to elucidate reaction mechanisms, including possible halogen bonding, and the search for more selective and potent inhibitors.

  DOI：

  10.1021/jp301561x
• 作为产物：
  描述：

  2,6-二溴-4-硝基苯胺 在 盐酸 、 tin 、 硫酸 、 氢溴酸 、 硝酸 作用下， 生成 3,4,5-tribromo-1,2-diaminobenzene
  参考文献：
  名称：

  Jackson; Fiske, American Chemical Journal, 1903, vol. 30, p. 68

  摘要：

  DOI：

文献信息

• Anti-bacterial polymer and method for the preparation thereof, anti-bacterial polymer film and method for the preparation thereof, and article having such a film on the surface thereof
  申请人：ULVAC, INC.

  公开号：EP1396514A1

  公开（公告）日：2004-03-10

  An anti-bacterial polymer of the present invention consists of a vapor deposition-polymerization reaction product of a diaminobenzoic acid monomer or halogen atom-containing diamine monomer and a monomer reactive with these monomers. The anti-bacterial polymer can be prepared by a method, which comprises the step of subjecting a gas obtained by evaporating a diaminobenzoic acid monomer or halogen atom-containing diamine monomer and a gas obtained by evaporating a monomer reactive with these monomers to vapor deposition-polymerization, in a vacuum, to thus form an anti-bacterial polymer. The method permits the formation of a film having a desired thickness even on the surface having a complicated shape such as the surface of, for instance, a heat exchanger.

  本发明的抗菌聚合物由二氨基苯甲酸单体或含卤原子的二胺单体和与这些单体反应的单体的气相沉积-聚合反应产物组成。抗菌聚合物的制备方法包括以下步骤：将蒸发二氨基苯甲酸单体或含卤素原子的二胺单体得到的气体和蒸发与这些单体反应的单体得到的气体在真空中进行气相沉积-聚合反应，从而形成抗菌聚合物。这种方法即使在形状复杂的表面（如热交换器表面）上也能形成具有所需厚度的薄膜。
• 1-halomercuri, trihalo benzimidazoles
  申请人：MERCK &

  公开号：US02876230A1

  公开（公告）日：1959-03-03
• US7279543B2
  申请人：——

  公开号：US7279543B2

  公开（公告）日：2007-10-09
• Synthesis and Physico-Chemical Properties in Aqueous Medium of All Possible Isomeric Bromo Analogues of Benzo-1H-Triazole, Potential Inhibitors of Protein Kinases
  作者：Romualda Wąsik、Patrycja Wińska、Jarosław Poznański、David Shugar

  DOI：10.1021/jp301561x

  日期：2012.6.21

  In ongoing studies on the role of the individual bromine atoms of 4,5,6,7-tetrabromobenzotriazole (TBBt) in its relatively selective inhibition of protein kinase CK2 alpha, we have prepared all the possible two mono-, four di-, and two tri-bromobenzotriazoles and determined their physicochemical properties in aqueous medium. They exhibited a general trend of a decrease in solubility with an increase in the number of bromines on the benzene ring, significantly modulated by the pattern of substitution. For a given number of attached bromines, this was directly related to the electronic effects resulting from different sites of substitution, leading to marked variations of pK(a) values for dissociation of the triazole proton. Experimental data (pK(a), solubility) and ab initio calculations demonstrated that hydration of halogenated benzotriazoles is driven by a subtle balance of hydrophobic and polar interactions. The combination of QM-derived free energies for solvation and proton dissociations was found to be a reasonably good predictor of inhibitory activity of halogenated benzotriazoles vs CK2 alpha. Since the pattern of halogenation of the benzene ring of benzotriazole has also been shown to be one of the determinants of inhibitory potency vs some viruses and viral enzymes, the present comprehensive description of their physicochemical properties should prove helpful in efforts to elucidate reaction mechanisms, including possible halogen bonding, and the search for more selective and potent inhibitors.
• Jackson; Fiske, American Chemical Journal, 1903, vol. 30, p. 68
  作者：Jackson、Fiske

  DOI：——

  日期：——