4,5,6-Tris(bromomethyl)-2-(methylthio)pyrimidine | 135665-31-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4,5,6-Tris(bromomethyl)-2-(methylthio)pyrimidine
• 英文别名: 4,5,6-tris(bromomethyl)-2-methylsulfanylpyrimidine
• CAS: 135665-31-5
• 化学式: C₈H₉Br₃N₂S
• 分子量: 404.951
• InChiKey: TWFZEBFWCNHIOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  51.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4,6-Bis(bromomethyl)-5-methyl-2-(methylthio)pyrimidine 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 0.67h， 以95%的产率得到4,5,6-Tris(bromomethyl)-2-(methylthio)pyrimidine
  参考文献：
  名称：

  Highly regioselective bromination reactions of polymethylpyrimidines

  摘要：

  4,5-Dimethyl- and 4,5,6-trimethyl-substituted pyrimidines are brominated at C5-Me with NBS in CCl4 and at C4(6)-Me with bromine in acetic acid to give the corresponding bromomethyl derivatives in a high yield. The remaining methyl group(s) can also be brominated with high regioselectivity. The 2-methylthio substituent is not oxidized under these conditions.

  DOI：

  10.1021/jo00019a028

文献信息

• Highly regioselective bromination reactions of polymethylpyrimidines
  作者：Lucjan Strekowski、Roman L. Wydra、Lubomir Janda、Donald B. Harden

  DOI：10.1021/jo00019a028

  日期：1991.9

  4,5-Dimethyl- and 4,5,6-trimethyl-substituted pyrimidines are brominated at C5-Me with NBS in CCl4 and at C4(6)-Me with bromine in acetic acid to give the corresponding bromomethyl derivatives in a high yield. The remaining methyl group(s) can also be brominated with high regioselectivity. The 2-methylthio substituent is not oxidized under these conditions.