3-amino-4-chloro-1,2,5-thiadiazole | 88905-76-4

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 3-amino-4-chloro-1,2,5-thiadiazole
• 英文别名: 3-Amino-4-chlor-1,2,5-thiadiazol；4-Chloro-1,2,5-thiadiazol-3-amine
• CAS: 88905-76-4
• 化学式: C₂H₂ClN₃S
• 分子量: 135.577
• InChiKey: BTLMBWIGUOCEGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 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：
  80
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  3-amino-4-chloro-1,2,5-thiadiazole 在 copper(l) iodide 、 亚硝酸特丁酯 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以41%的产率得到3-chloro-4-iodo-1,2,5-thiadiazole
  参考文献：
  名称：

  The Palladium-catalyzed Cross-Coupling Reactions of 3-Chloro-4-halogeno-1,2,5-thiadiazoles

  摘要：

  3,4-Dichloro- and 3-chloro-4-halogeno-1,2,5-thiadiazoles (halogeno-: bromo- and iodo-) are involved in Pd-catalyzed cross-coupling reactions under Stille and Suzuki conditions. As a result, by using the commercially available 3,4-dichloro-1,2,5-thiadiazole as substrate, several 3-alkyl-, 3-alkenyl-, 3-alkynyl-and 3-aryl-4-chloro-1,2,5-thiadiazoles can easily be prepared. However, these reactions through direct desymmetrization of the 3,4-dichloro-1,2,5-thiadiazole always occur with side-reactions resulting from the concurrent decomposition of the heterocyclic ring of the starting material. These problems are resolved by involving, in these Pd-catalyzed cross-coupling reactions, the more reactive and selective 3-bromo-4-chloro- and 3-chloro-4-iodo-1,2,5-thiadiazole. These new dihalogeno-1,2,5-thiadiazoles can easily be prepared, via diazotization reaction followed by halogen substitution, from the 3-amino-4-chloro-1,2,5-thiadiazole.

  DOI：

  10.3987/com-02-9550

文献信息

• Palladium-catalyzed cross-coupling chemistry on 3-chloro-4-halo-1,2,5-thiadiazole
  申请人：Eli Lilly and Company

  公开号：US06620940B1

  公开（公告）日：2003-09-16

  The present invention relates to 3-chloro-4-halo-1,2,5-thiadiazole compounds, a method of producing novel mono- and di-substituted-1,2,5-thiadiazoles therefrom, as well as mono- and di-substituted -1,2,5-thiadiazoles.

  本发明涉及3-氯-4-卤代-1,2,5-噻二唑化合物，以及生产新型单取代和双取代-1,2,5-噻二唑的方法，还涉及单取代和双取代-1,2,5-噻二唑。