2-bromo-5-chloro-4-phenylthiazole | 1403935-16-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-bromo-5-chloro-4-phenylthiazole
• 英文别名: 2-Bromo-5-chloro-4-phenyl-1,3-thiazole；2-bromo-5-chloro-4-phenyl-1,3-thiazole
• CAS: 1403935-16-9
• 化学式: C₉H₅BrClNS
• 分子量: 274.568
• InChiKey: PUFCVTTWYBAMCJ-UHFFFAOYSA-N

物化性质

• 沸点：
  341.7±22.0 °C(Predicted)
• 密度：
  1.658±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• 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

• 作为反应物：
  描述：

  2-bromo-5-chloro-4-phenylthiazole 在 sodium tetrahydroborate 、 四甲基乙二胺 、 PdCl2(1,1′-bis(di-tertbutylphosphino)ferrocene) 、 palladium diacetate 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 29.0h， 生成 4-苯基噻唑
  参考文献：
  名称：

  Room-Temperature Hydrodehalogenation of Halogenated Heteropentalenes with One or Two Heteroatoms

  摘要：

  The pair NaBH4-TMEDA as a hydride source and catalytic PdCl2(4ppf) in THF prove to be an efficient system for the hydrodehalogenation of bromo(chloro)-heteropentalenes. with one or two heteroatoms, while Pd(OAc)(2)/PPh3 is able to reduce reactive haloheteropentalenes, and PdCl2(tbpf) allows the removal of the 2-chlorine from a thiophene ring. The reaction conditions tolerate various functional groups, allowing highly chemoselective reactions in the presence of halide, ester, alkyne, alkene, and nitrile substituents and also showing good efficiency in the regioselective hydrodehalogenation of a variety of polyhalogenated substrates.

  DOI：

  10.1021/jo3019335
• 作为产物：
  描述：

  2-溴-4-苯基噻唑 在 N-氯代丁二酰亚胺 作用下， 以 乙腈 为溶剂， 反应 31.0h， 以96%的产率得到2-bromo-5-chloro-4-phenylthiazole
  参考文献：
  名称：

  Room-Temperature Hydrodehalogenation of Halogenated Heteropentalenes with One or Two Heteroatoms

  摘要：

  The pair NaBH4-TMEDA as a hydride source and catalytic PdCl2(4ppf) in THF prove to be an efficient system for the hydrodehalogenation of bromo(chloro)-heteropentalenes. with one or two heteroatoms, while Pd(OAc)(2)/PPh3 is able to reduce reactive haloheteropentalenes, and PdCl2(tbpf) allows the removal of the 2-chlorine from a thiophene ring. The reaction conditions tolerate various functional groups, allowing highly chemoselective reactions in the presence of halide, ester, alkyne, alkene, and nitrile substituents and also showing good efficiency in the regioselective hydrodehalogenation of a variety of polyhalogenated substrates.

  DOI：

  10.1021/jo3019335

文献信息

• NaBH4-TMEDA and a palladium catalyst as efficient regio- and chemoselective system for the hydrodehalogenation of halogenated heterocycles
  作者：Giorgio Chelucci、Susanna Figus

  DOI：10.1016/j.molcata.2014.06.012

  日期：2014.11