2-phenylbenzo[d][1,2,3]thiadiazol-2-ium bromide | 29770-15-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻二唑类
• 英文名称: 2-phenylbenzo[d][1,2,3]thiadiazol-2-ium bromide
• 英文别名: 2-Phenyl-1,2,3-benzothiadiazol-2-ium;bromide；2-phenyl-1,2,3-benzothiadiazol-2-ium;bromide
• CAS: 29770-15-8
• 化学式: Br*C₁₂H₉N₂S
• 分子量: 293.187
• InChiKey: OZVLYABPUHXBSY-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.42
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-phenylbenzo[d][1,2,3]thiadiazol-2-ium bromide 、 间苯二胺 以 水 为溶剂， 反应 0.08h， 以82%的产率得到2,4-diaminophenyl o-phenylazophenyl sulfide
  参考文献：
  名称：

  One-Pot, Catalyst-Free, Facile, and Efficient Sulfenylation of Electron-Rich Substrates with a Mild Sulfenium Carrier Azobenzene-2-sulfenyl Bromide

  摘要：

  One-pot, catalyst-free, facile, and efficient sulfenylations of resorcinol, 1,3-diaminobenzene, 2-naphthol, 2-aminonaphthalene, indole, pentane-2,4-dione, etc., in aqueous and ethanolic solution by a mild sulfenium carrier azobenzene-2-sulfenyl bromide are described. Efficient sulfenylating reagent, mild reaction conditions, and excellent yields make this method quite simple, convenient, and practical. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2012.733476
• 作为产物：
  描述：

  2-(benzylthio)azobenzene 在 tetra-N-butylammonium tribromide 、 溶剂黄146 作用下， 反应 0.08h， 以94%的产率得到2-phenylbenzo[d][1,2,3]thiadiazol-2-ium bromide
  参考文献：
  名称：

  Antibacterial Investigation and Structural Study on Few ortho-Mercapto-azo Compounds by Spectroscopic Techniques and DFT Calculation

  摘要：

  一种高效合成二价邻硫基偶氮化合物的方法已经应用，该方法采用了绿色还原、离子液体的缩合和绿色去苄基化等步骤。这些更环保的步骤提供了更高的产率、更短的反应时间和简单的工作流程等优点。密度泛函理论（DFT）计算和XRD分析证明了这些化合物的离子性质，因为亲电性硫原子和邻位偶氮基之间发生了分子内环化，形成了2-芳基苯并-1-硫-2,3-二氮杂唑-2-ium（BTD +）溴化物。在BTD + 溴化物中，亲电性硫原子中存在一定程度的LUMO轨道。这些硫醇溴化物也被发现对抗抗菌菌株具有活性。

  DOI：

  10.14233/ajchem.2022.23768

文献信息

• One-Pot, Catalyst-Free, Facile, and Efficient Sulfenylation of Electron-Rich Substrates with a Mild Sulfenium Carrier Azobenzene-2-sulfenyl Bromide
  作者：Nizamuddin Ahmed、Tirtha Bhattacharjee、Pranjit Barman、Saibal Kanti Bhattacharjee

  DOI：10.1080/00397911.2012.733476

  日期：2013.10.2

  One-pot, catalyst-free, facile, and efficient sulfenylations of resorcinol, 1,3-diaminobenzene, 2-naphthol, 2-aminonaphthalene, indole, pentane-2,4-dione, etc., in aqueous and ethanolic solution by a mild sulfenium carrier azobenzene-2-sulfenyl bromide are described. Efficient sulfenylating reagent, mild reaction conditions, and excellent yields make this method quite simple, convenient, and practical. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.
• Antibacterial Investigation and Structural Study on Few ortho-Mercapto-azo Compounds by Spectroscopic Techniques and DFT Calculation
  作者：Murshida Karim、Nizamuddin Ahmed

  DOI：10.14233/ajchem.2022.23768

  日期：——

  An efficient method has been applied for the synthesis of bivalent ortho-mercapto-azo compounds by using green reduction, condensation using ionic liquid and green debenzylation. These greener steps provide the benefits like higher yields, shorter reaction times and simple work-up. Density functional theory (DFT) calculation and XRD analysis proved the ionic nature of these compounds as 2-arylbenzo-1-thia-2,3-diazol-2-ium (BTD+) bromide due to intramolecular cyclization between electrophilic sulfur atom and ortho-azo group. Some extent of LUMO orbital is present in electrophilic sulfur atom in BTD+ bromides. These sulfenyl bromides were also found to be active against antibacterial strains.

  一种高效合成二价邻硫基偶氮化合物的方法已经应用，该方法采用了绿色还原、离子液体的缩合和绿色去苄基化等步骤。这些更环保的步骤提供了更高的产率、更短的反应时间和简单的工作流程等优点。密度泛函理论（DFT）计算和XRD分析证明了这些化合物的离子性质，因为亲电性硫原子和邻位偶氮基之间发生了分子内环化，形成了2-芳基苯并-1-硫-2,3-二氮杂唑-2-ium（BTD +）溴化物。在BTD + 溴化物中，亲电性硫原子中存在一定程度的LUMO轨道。这些硫醇溴化物也被发现对抗抗菌菌株具有活性。