5-chloro-2-(3-bromophenyl)benzothiazole | 1233731-00-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 5-chloro-2-(3-bromophenyl)benzothiazole
• 英文别名: 6-chloro-2-(3-bromophenyl)benzothiazole；2-(3-Bromophenyl)-5-chloro-1,3-benzothiazole；2-(3-bromophenyl)-5-chloro-1,3-benzothiazole
• CAS: 1233731-00-4
• 化学式: C₁₃H₇BrClNS
• 分子量: 324.628
• InChiKey: CIKMUKSSMVMTNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  17
• 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：
  41.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  间溴苯甲腈 、 2-氨基-4-氯苯硫醇 在 三氟甲磺酸 作用下， 以 neat (no solvent) 为溶剂， 反应 12.0h， 以71%的产率得到5-chloro-2-(3-bromophenyl)benzothiazole
  参考文献：
  名称：

  通过布朗斯台德酸催化的2-氨基苯硫酚与腈的环化反应合成2-取代的苯并噻唑

  摘要：

  描述了一种由简单且容易获得的2-氨基苯硫酚和腈合成2-取代的苯并噻唑的简便有效的方法。布朗斯台德酸催化的环化反应在无金属和无溶剂条件下进行。

  DOI：

  10.1016/j.tetlet.2019.06.039

文献信息

• Ru(III)-catalyzed oxidative reaction in ionic liquid: an efficient and practical route to 2-substituted benzothiazoles and their hybrids with pyrimidine nucleoside
  作者：Xuesen Fan、Yangyang Wang、Yan He、Xinying Zhang、Jianji Wang

  DOI：10.1016/j.tetlet.2010.04.050

  日期：2010.7

  environmentally benign synthesis of 2-substituted benzothiazoles was developed through RuCl3-catalyzed oxidative condensation of 2-aminothiophenol with aldehyde in ionic liquid by using air as the oxidant. With this procedure, a series of 2-substituted benzothiazoles and benzothiazole/pyrimidine nucleoside hybrids with antimicrobial activities were efficiently prepared from easily accessible starting materials

  通过使用空气作为氧化剂，通过RuCl 3催化2-氨基硫酚与醛在离子液体中的氧化缩合反应，开发了一种高效，实用且对环境有益的合成2-取代的苯并噻唑的方法。通过这种方法，可以从易于获得的起始原料中高效制备一系列具有抗菌活性的2-取代的苯并噻唑和苯并噻唑/嘧啶核苷杂化物。
• Synthesis of benzothiazoles using fluorescein as an efficient photocatalyst under visible light
  作者：Wuji Sun、Haodong Chen、Kaixuan Wang、Xueyao Wang、Mayan Lei、Chunyan Liu、Qidi Zhong

  DOI：10.1016/j.mcat.2021.111693

  日期：2021.6

  This work reports a novel and efficient method for the synthesis of benzothiazoles using 2-aminothiophenol derivatives in conjunction with aromatic aldehyde as starting materials via visible-light-induced condensation cyclization. Utilizing fluorescein as the photocatalyst and blue LED lamp as the light source, the reaction proceeds in the presence of a molecular oxygen atmosphere without the need

  这项工作报告了一种使用 2-氨基苯硫酚衍生物与芳香醛作为起始材料，通过可见光诱导的缩合环化合成苯并噻唑的新型有效方法。利用荧光素作为光催化剂，蓝色LED灯作为光源，反应在分子氧气氛中进行，不需要金属催化剂或额外的氧化剂。值得注意的是，该方法对底物具有良好的耐受性，并且各种 2-氨基苯硫酚衍生物和芳香醛都能够以高产率生产相应的苯并噻唑。
• One-pot approach for the synthesis of 2-aryl benzothiazoles via a two-component coupling of gem-dibromomethylarenes and o-aminothiophenols
  作者：Chandrappa Siddappa、Vinaya Kambappa、Muddegowda Umashankara、Kanchugarakoppal S. Rangappa

  DOI：10.1016/j.tetlet.2011.08.055

  日期：2011.10

  One-pot synthesis of 2-aryl benzothiazoles from gem-dibromomethylarenes using 2-aminoarylthiols is described. Benzothiazoles were obtained in high chemical yields under mild conditions. This transformation would facilitate synthesis by short reaction times, large-scale synthesis, easy and quick isolation of the products, which are the main advantages of this procedure. (C) 2011 Published by Elsevier Ltd.
• Synthesis of 2-substituted benzothiazoles via the Brønsted acid catalyzed cyclization of 2-amino thiophenols with nitriles
  作者：Xiaoqiang Yu、Qing Yin、Zhiheng Zhang、Tianyu Huang、Zichao Pu、Ming Bao

  DOI：10.1016/j.tetlet.2019.06.039

  日期：2019.7

  A convenient and efficient method for the synthesis of 2-substituted benzothiazoles from simple and readily available 2-amino thiophenols and nitriles is described. The Brønsted acid-catalyzed cyclization reaction was performed under metal and solvent-free conditions.

  描述了一种由简单且容易获得的2-氨基苯硫酚和腈合成2-取代的苯并噻唑的简便有效的方法。布朗斯台德酸催化的环化反应在无金属和无溶剂条件下进行。