1-(二溴甲基)-2,3,4,5,6-五氟苯 | 887266-89-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(二溴甲基)-2,3,4,5,6-五氟苯
• 英文名称: Dibromomethylpentafluorobenzene
• 英文别名: 1-(dibromomethyl)-2,3,4,5,6-pentafluorobenzene
• CAS: 887266-89-9
• 化学式: C₇HBr₂F₅
• 分子量: 339.885
• InChiKey: SCGYCYOVWSMRBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2903999090

反应信息

• 作为产物：
  描述：

  2,3,4,5,6-五氟甲苯 在 N-溴代丁二酰亚胺(NBS) 作用下， 反应 18.0h， 生成 1-(二溴甲基)-2,3,4,5,6-五氟苯 、 α-溴-2,3,4,5,6-五氟甲基苯酸酯
  参考文献：
  名称：

  可见光促进的Wohl – Ziegler在无溶剂条件下用N-溴代琥珀酰亚胺对有机分子进行官能化

  摘要：

  Abstractmagnified imageThe visible‐light‐induced transformation of toluenes with N‐bromosuccinimide (NBS) under solvent‐free reaction conditions (SFRC) was studied. The reaction took place in spite of the very restricted molecular motion; toluenes could be regioselectively converted to benzyl bromides. Selective radical‐chain reactions with NBS were carried out in liquid/liquid and in solid/solid systems; furthermore, reactions could be performed in the presence of air. The radical scavenger TEMPO (=2,2,6,6‐tetramethylpiperidin‐1‐yloxy) completely suppressed the side‐chain bromination of toluenes with NBS under SFRC. Electron‐withdrawing groups decreased the reactivity of the toluenes, and the Hammett reaction constant ρ+=−1.7 indicated involvement of polar radical intermediates with electrophilic character.

  DOI：

  10.1002/hlca.200800308

文献信息

• Visible-Light-Promoted<i>Wohl</i>-<i>Ziegler</i>Functionalization of Organic Molecules with<i>N</i>-Bromosuccinimide under Solvent-Free Reaction Conditions
  作者：Marjan Jereb、Marko Zupan、Stojan Stavber

  DOI：10.1002/hlca.200800308

  日期：2009.3

  Abstractmagnified imageThe visible‐light‐induced transformation of toluenes with N‐bromosuccinimide (NBS) under solvent‐free reaction conditions (SFRC) was studied. The reaction took place in spite of the very restricted molecular motion; toluenes could be regioselectively converted to benzyl bromides. Selective radical‐chain reactions with NBS were carried out in liquid/liquid and in solid/solid systems; furthermore, reactions could be performed in the presence of air. The radical scavenger TEMPO (=2,2,6,6‐tetramethylpiperidin‐1‐yloxy) completely suppressed the side‐chain bromination of toluenes with NBS under SFRC. Electron‐withdrawing groups decreased the reactivity of the toluenes, and the Hammett reaction constant ρ+=−1.7 indicated involvement of polar radical intermediates with electrophilic character.