3-溴-4-苯基-1,2,5-噻二唑 | 151133-39-0

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 中文名称: 3-溴-4-苯基-1,2,5-噻二唑
• 英文名称: 3-Bromo-4-phenyl-[1,2,5]thiadiazole
• 英文别名: 3-Bromo-4-phenyl-1,2,5-thiadiazole
• CAS: 151133-39-0
• 化学式: C₈H₅BrN₂S
• 分子量: 241.111
• InChiKey: VWGNTXXMTIVDGZ-UHFFFAOYSA-N

物化性质

• 沸点：
  309.8±22.0 °C(Predicted)
• 密度：
  1.642±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  12
• 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：
  54
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  三丁基(4-氯苯基)锡烷 、 3-溴-4-苯基-1,2,5-噻二唑 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以90%的产率得到3-(4-chloro-phenyl)-4-phenyl-[1,2,5]thiadiazole
  参考文献：
  名称：

  Synthesis of 3-Alkyl-4-aryl- and 3,4-Diaryl-1,2,5-thiadiazoles via Palladium-catalyzed Cross-Coupling Reaction

  摘要：

  4-Substituted 3-aryl-1,2,5-thiadiazoles were synthesized by palladium-catalyzed cross-coupling reaction of arylstannane with easily available 4-substituted 3-halogeno- and 3-trifluoromethylsulfonyloxy-1,2,5-thiadiazoles.

  DOI：

  10.3987/com-96-7567
• 作为产物：
  描述：

  4-phenyl-1,2,5-thiadiazol-3-ol 在 三溴氧磷 作用下， 反应 12.0h， 以80%的产率得到3-溴-4-苯基-1,2,5-噻二唑
  参考文献：
  名称：

  Synthesis of 3-Alkyl-4-aryl- and 3,4-Diaryl-1,2,5-thiadiazoles via Palladium-catalyzed Cross-Coupling Reaction

  摘要：

  4-Substituted 3-aryl-1,2,5-thiadiazoles were synthesized by palladium-catalyzed cross-coupling reaction of arylstannane with easily available 4-substituted 3-halogeno- and 3-trifluoromethylsulfonyloxy-1,2,5-thiadiazoles.

  DOI：

  10.3987/com-96-7567

文献信息

• Reactions of 1-aryl-2,2-dihalogenoethanone oximes with tetrasulfur tetranitride (S4N4): a general method for the synthesis of 3-aryl-4-halogeno-1,2,5-thiadiazoles
  作者：Sung Cheol Yoon、Jaeeock Cho、Kyongtae Kim

  DOI：10.1039/a704408i

  日期：——

  on the basis of 1H NMR spectroscopic evidence and an X-ray crystallographic analysis of 1-(3-chlorophenyl)-2,2-dichloroethanone oxime 7f. The 1-aryl-2,2-dihalogenoethanone oximes react with tetrasulfur tetranitride in refluxing 1,4-dioxane to give 3-aryl-4-chloro-1, 3-aryl-4-bromo-2, and 3-aryl-4-fluoro-1,2,5-thiadiazoles 3 in 69–98, 49–99, and 32–65% yields, respectively. A mechanism for the formation

  1-芳基-2,2-二氯-7、1-芳基-2,2-二溴-8、1-芳基-2-溴-2-氟-9和1-芳基-2-氯-2-氟-通过在室温下在EtOH中使相应的酮与盐酸羟胺反应来制备乙酮肟10。在1 H NMR光谱证据和1-（3-氯苯基）-2,2-二氯乙酮肟7f的X射线晶体学分析的基础上，对肟进行立体化学分配。1-芳基-2,2-二卤代乙酮肟与四氮化四硫反应，回流1,4-二恶烷，得到3-芳基-4-氯-1、3-芳基-4-溴-2和3-芳基-4 -氟-1,2,5-噻二唑3的产率分别为69-98、49-99和32-65％。提出了形成1,2,5-噻二唑的机理。
• Reactions of Monohalomethyl Aryl Ketoximes with Tetrasulfur Tetranitride: Much Improved Synthesis of 3-Aryl-1,2,5-thiadiazoles
  作者：Kyongtae Kim、Jaeeock Cho

  DOI：10.3987/com-94-6755

  日期：——

  Reactions of chloromethyl aryl ketoximes (1, X = Cl) with tetrasulfur tetranitride in p-dioxane at reflux for 4 h afforded 3-aryl-1,2,5-thiadiazoles (2) in 37-92% yields, whereas those of bromo analogs under the same conditions gave 2 and 3-aryl-4-bromo-1,2,5-thiadiazoles (3) in 48-81% and 17-31% yields, respectively. However, the compounds (3) were not formed in the presence of pyridine. Alpha-nitrosostyrene and its ring-substituted derivatives (4) are proposed as intermediates for the formations of 2.
• Kim Kyongtae, Cho Jaecock, Heterocycles, 38 (1994) N 8, S 1859-1866
  作者：Kim Kyongtae, Cho Jaecock

  DOI：——

  日期：——
• Synthesis of 3-Alkyl-4-aryl- and 3,4-Diaryl-1,2,5-thiadiazoles via Palladium-catalyzed Cross-Coupling Reaction
  作者：Yasuaki Hanasaki

  DOI：10.3987/com-96-7567

  日期：——

  4-Substituted 3-aryl-1,2,5-thiadiazoles were synthesized by palladium-catalyzed cross-coupling reaction of arylstannane with easily available 4-substituted 3-halogeno- and 3-trifluoromethylsulfonyloxy-1,2,5-thiadiazoles.