2,2-bis(trifluoromethyl)cycloprop-1-ylmethyl bromide | 390388-89-3

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氟化物
• 英文名称: 2,2-bis(trifluoromethyl)cycloprop-1-ylmethyl bromide
• 英文别名: 2-(Bromomethyl)-1,1-bis(trifluoromethyl)cyclopropane
• CAS: 390388-89-3
• 化学式: C₆H₅BrF₆
• 分子量: 271.0
• InChiKey: IYONZRWCWLUJLM-UHFFFAOYSA-N

物化性质

• 沸点：
  126.3±35.0 °C(Predicted)
• 密度：
  1.782±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,2-bis(trifluoromethyl)cycloprop-1-ylmethyl bromide 、 4-[trans-4-(trans-4-propylcyclohexyl)cyclohexyl]phenol 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 7.0h， 以21%的产率得到1-[2,2-bis(trifluoromethyl)cycloprop-1-ylmethyleneoxy]-4-[trans-4-(trans-4-propylcyclohexyl)cyclohexyl]benzene
  参考文献：
  名称：

  Liquid Crystalline Compounds with 2,2-Disubstituted Cyclopropane End Groups in their Side Chains

  摘要：

  Novel liquid crystalline compounds with racemic and enantiomerically pure 2,2-difluoro-, 2,2-dichloro-, 2,2-dibromo-, and 2,2-bis(trifluoromethyl)-cyclopropane-1-carboxylate end groups have been synthesized. The Ps values, tilt angles, and response times of SmC* mixtures containing 10 wt% of the novel optically active liquid crystalline compounds in a SmC base mixture were measured. and the potential of the novel compounds as chiral dopants for ferroelectric liquid crystal mixtures was estimated. The novel liquid crystalline compounds with racemic bis(trifluoromethyl)cyclopropane have a remarkably strong tendency to form smectic phases SmB and SmA. The bistrifluoromethyl derivatives exhibited only SmB and SmA phases although the corresponding compounds with 2,2-difluoro-, 2,2-dichloro-, and 2,2-dibromocyclopropane rings showed nematic or chiral nematic phases. In some cases, almost perfect substitutions of the nematic phases by the smectic phases upon changing the substituents from halogen to trifluoromethyl were observed.

  DOI：

  10.1080/10587250108025023
• 作为产物：
  描述：

  2,2-bis(trifluoromethyl)cycloprop-1-ylmethanol 在 吡啶 、 溴 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以94%的产率得到2,2-bis(trifluoromethyl)cycloprop-1-ylmethyl bromide
  参考文献：
  名称：

  Liquid Crystalline Compounds with 2,2-Disubstituted Cyclopropane End Groups in their Side Chains

  摘要：

  Novel liquid crystalline compounds with racemic and enantiomerically pure 2,2-difluoro-, 2,2-dichloro-, 2,2-dibromo-, and 2,2-bis(trifluoromethyl)-cyclopropane-1-carboxylate end groups have been synthesized. The Ps values, tilt angles, and response times of SmC* mixtures containing 10 wt% of the novel optically active liquid crystalline compounds in a SmC base mixture were measured. and the potential of the novel compounds as chiral dopants for ferroelectric liquid crystal mixtures was estimated. The novel liquid crystalline compounds with racemic bis(trifluoromethyl)cyclopropane have a remarkably strong tendency to form smectic phases SmB and SmA. The bistrifluoromethyl derivatives exhibited only SmB and SmA phases although the corresponding compounds with 2,2-difluoro-, 2,2-dichloro-, and 2,2-dibromocyclopropane rings showed nematic or chiral nematic phases. In some cases, almost perfect substitutions of the nematic phases by the smectic phases upon changing the substituents from halogen to trifluoromethyl were observed.

  DOI：

  10.1080/10587250108025023