2-溴-4-碘噻唑 | 108306-63-4

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-溴-4-碘噻唑
• 中文别名: 2-溴-5-碘噻唑
• 英文名称: 2-bromo-5-iodo-thiazole
• 英文别名: 2-Bromo-5-iodothiazole；2-bromo-5-iodo-1,3-thiazole
• CAS: 108306-63-4
• 化学式: C₃HBrINS
• 分子量: 289.922
• InChiKey: MWJCQTBRSKINNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  7
• 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：
  41.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2934100090
• 包装等级：
  III
• 危险类别：
  6.1
• 危险性防范说明：
  P261,P264,P270,P271,P280,P302+P352,P304+P340,P310,P330,P361,P403+P233,P405,P501
• 危险品运输编号：
  2811
• 危险性描述：
  H301,H311,H331

反应信息

• 作为反应物：
  描述：

  2-氯噻唑 、 2-溴-4-碘噻唑 在 四(三苯基膦)钯 正丁基锂 、 二异丙胺 、 三丁基氯化锡 作用下， 以 四氢呋喃 、 正己烷 、 乙醚 、 苯 为溶剂， 反应 0.5h， 以156 mg的产率得到2-chloro-5,5'-bithiazole
  参考文献：
  名称：

  Halogenated 2‘-Chlorobithiazoles via Pd-Catalyzed Cross-Coupling Reactions

  摘要：

  Halogenated bithiazoles allow facile further functionalization and are, therefore, suitable intermediates for the synthesis of compounds with interesting biological activity or material science properties. The applicability of three coupling methods (Negishi, Suzuki, and Stille) for the synthesis of the title compounds was compared. The Negishi method proved to be troublesome, and side reactions were predominant. The synthesis of the first thiazoleboronic acid ester offered a new method for the formation of bithiazoles, not generally applicable so far. The lower toxicity compared to that of tin organyls make this method an approach with interesting perspectives. The Stille coupling proved to be superior to the other methods and enabled the synthesis of the title compounds with diverse connectivity.

  DOI：

  10.1021/jo0601009
• 作为产物：
  描述：

  2-(trimethylsilyl)-5-(trimethylstannyl)-thiazole 以35%的产率得到
  参考文献：
  名称：

  DONDONI A.; MASTELLARI A. R.; MEDICI A.; NEGRINI E.; PEDRINI P., SYNTHESIS,(1986) N 9, 757-760

  摘要：

  DOI：

文献信息

• Synthesis of Stannylthiazoles and Mixed Stannylsilylthiazoles and their Use for a Convenient Preparation of Mono- and Bis-halothiazoles
  作者：A. Dondoni、A. R. Mastellari、A. Medici、E. Negrini、P. Pedrini

  DOI：10.1055/s-1986-31766

  日期：——

  Stannylthiazoles and stannyl-silylthiazoles have been prepared and employed as thiazolyl carbanion equivalents in reactions with halogens to give mono- and mixed bis-halothiazoles in good yields.

  已制备出锡噻唑和锡基硅噻唑，并在与卤素的反应中用作噻唑基碳原子等价物，从而以良好的收率得到单-和混合双-卤代噻唑。
• (tmp)2Zn⋅2 MgCl2⋅2 LiCl: A Chemoselective Base for the Directed Zincation of Sensitive Arenes and Heteroarenes
  作者：Stefan H. Wunderlich、Paul Knochel

  DOI：10.1002/anie.200701984

  日期：2007.10.8
• DONDONI A.; MASTELLARI A. R.; MEDICI A.; NEGRINI E.; PEDRINI P., SYNTHESIS,(1986) N 9, 757-760
  作者：DONDONI A.、 MASTELLARI A. R.、 MEDICI A.、 NEGRINI E.、 PEDRINI P.

  DOI：——

  日期：——
• Halogenated 2‘-Chlorobithiazoles via Pd-Catalyzed Cross-Coupling Reactions
  作者：Peter Stanetty、Michael Schnürch、Marko D. Mihovilovic

  DOI：10.1021/jo0601009

  日期：2006.5.1

  Halogenated bithiazoles allow facile further functionalization and are, therefore, suitable intermediates for the synthesis of compounds with interesting biological activity or material science properties. The applicability of three coupling methods (Negishi, Suzuki, and Stille) for the synthesis of the title compounds was compared. The Negishi method proved to be troublesome, and side reactions were predominant. The synthesis of the first thiazoleboronic acid ester offered a new method for the formation of bithiazoles, not generally applicable so far. The lower toxicity compared to that of tin organyls make this method an approach with interesting perspectives. The Stille coupling proved to be superior to the other methods and enabled the synthesis of the title compounds with diverse connectivity.