4,5-dibromo-2-(trifluoromethyl)imidazole | 81654-03-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4,5-dibromo-2-(trifluoromethyl)imidazole
• 英文别名: 4,5-dibromo-2-(trifluoromethyl)-1H-imidazole
• CAS: 81654-03-7
• 化学式: C₄HBr₂F₃N₂
• 分子量: 293.869
• InChiKey: ZIQQYRYCVXRBPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,5-dibromo-2-(trifluoromethyl)imidazole 以 异丙醇 为溶剂， 反应 48.0h， 以87%的产率得到4-dibromo-2-(trifluoromethyl)imidazole
  参考文献：
  名称：

  Syntheses of (Trifluoromethyl)imidazoles with Additional Electronegative Substituents. An Approach to Receptor-Activated Affinity Labels

  摘要：

  Electrophilic substitution in 2- and 4-(trifluoromethyl)imidazoles provides derivatives containing one or two nitro, chloro, bromo, or iodo groups. Fluoro and chloro derivatives were also prepared by photochemical trifluoromethylation of the respective haloimidazole. The results demonstrate that (trifluoromethyl)imidazoles behave fairly typically under the conditions of electrophilic nitration and halogenation. Of the alternative routes to the desired bifunctional and trifunctional imidazoles, electrophilic substitution on the preformed (trifluoromethyl)imidazole appears to be the method of choice in most cases. A large number of the products show herbicidal or insecticidal activity.

  DOI：

  10.1021/jo9814952
• 作为产物：
  描述：

  2-(三氟甲基)-1H-咪唑 在 溴 、 三乙胺 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 0.5h， 以82%的产率得到4,5-dibromo-2-(trifluoromethyl)imidazole
  参考文献：
  名称：

  Syntheses of (Trifluoromethyl)imidazoles with Additional Electronegative Substituents. An Approach to Receptor-Activated Affinity Labels

  摘要：

  Electrophilic substitution in 2- and 4-(trifluoromethyl)imidazoles provides derivatives containing one or two nitro, chloro, bromo, or iodo groups. Fluoro and chloro derivatives were also prepared by photochemical trifluoromethylation of the respective haloimidazole. The results demonstrate that (trifluoromethyl)imidazoles behave fairly typically under the conditions of electrophilic nitration and halogenation. Of the alternative routes to the desired bifunctional and trifunctional imidazoles, electrophilic substitution on the preformed (trifluoromethyl)imidazole appears to be the method of choice in most cases. A large number of the products show herbicidal or insecticidal activity.

  DOI：

  10.1021/jo9814952

文献信息

• Deoxofluorination of (Hetero)aromatic Acids
  作者：Serhii Trofymchuk、Maksym Ya. Bugera、Anton A. Klipkov、Bohdan Razhyk、Sergey Semenov、Karen Tarasenko、Viktoriia S. Starova、Olga A. Zaporozhets、Oksana Yu. Tananaiko、Anatoliy N. Alekseenko、Yurii Pustovit、Oleksandr Kiriakov、Igor I. Gerus、Andrei A. Tolmachev、Pavel K. Mykhailiuk

  DOI：10.1021/acs.joc.9b03011

  日期：2020.3.6

  Diverse trifluoromethyl-substituted compounds were synthesized by deoxofluorination of cinnamic and (hetero)aromatic carboxylic acids with sulfur tetrafluoride. The obtained products were used as starting materials in the preparation of novel fluorinated amino acids, anilines, and aliphatic amines - valuable building blocks for medicinal chemistry and agrochemistry.

  通过用四氟化硫对肉桂酸和（杂）芳族羧酸进行脱氧氟化反应，合成了不同的三氟甲基取代的化合物。所得产物用作制备新型氟化氨基酸，苯胺和脂肪胺的原料，这些氟化物是药物化学和农业化学的重要组成部分。