1-bromo-5-(trifluoromethyl)-2-(trimethylsilyl)benzene | 632324-50-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-bromo-5-(trifluoromethyl)-2-(trimethylsilyl)benzene
• 英文别名: 2-bromo-4-(trifluoromethyl)-1-(trimethylsilyl)benzene；1-[2-bromo-4-(trifluoromethyl)phenyl]trimethylsilane；1-bromo-5-trifluoromethyl-2-(trimethylsilyl)benzene；Silane, [2-bromo-4-(trifluoromethyl)phenyl]trimethyl-；[2-bromo-4-(trifluoromethyl)phenyl]-trimethylsilane
• CAS: 632324-50-6
• 化学式: C₁₀H₁₂BrF₃Si
• 分子量: 297.19
• InChiKey: YCFYZGJLTRLUJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.01
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  硼酸三甲酯 、 1-bromo-5-(trifluoromethyl)-2-(trimethylsilyl)benzene 在 正丁基锂 、 硫酸 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 反应 1.0h， 以42%的产率得到5-(trifluoromethyl)-2-(trimethylsilyl)phenylboronic acid
  参考文献：
  名称：

  Electrophilic ipso-iodination of silylated arylboronic acids

  摘要：

  Silylated functionalized arylboronic acids were converted into corresponding iodinated arylboronic acids in good yields via the electrophilic ipso-desilylation effected with iodine chloride in refluxing CHCl3. Disilylated arylboronic acids were susceptible to diiodination. In addition, the structural characterization and reactivity of a novel sterically hindered ortho-silylated diarylborinic ester were reported. The potential of selected iodinated phenylboronic acids as monomers for the SuzukieMiyaura cross-coupling polymerization was demonstrated. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2010.08.016
• 作为产物：
  描述：

  三甲基氯硅烷 、 间溴三氟甲苯 在 2,2,6,6-四甲基哌啶 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 以75%的产率得到1-bromo-5-(trifluoromethyl)-2-(trimethylsilyl)benzene
  参考文献：
  名称：

  拥挤的中继传播：作为空间压力发射体和传递体的三氟甲基基团

  摘要：

  而锂 2,2,6,6-四甲基哌啶 (LITMP) 摘要。仅来自 3-溴代三氟化物的 4-位的质子，当在 N,N,N',N'',N''-五甲基二亚乙基三胺和叔丁醇钾存在下使用时，相同的碱基选择性地攻击 2-位（ qFaigl mixq)。1-Bromo-3,5-双(三氟甲基)苯也在2-位发生金属化，但[2-溴-4-(三氟甲基)苯基]硅烷根本不反应，显然被C-SiR3/ C-Br 支撑作用。2-Bromo-4-(trifluoromethyl)pyridine，氮杂类似于母体模型芳烃 3-溴三氟化物，以及苯并氮杂类似的 2-bromo-4-(trifluoromethyl)quinoline 及其区域转化异构体 4-bromo-2-(三氟甲基）喹啉再次在 Br 和 CF3 侧翼位置容易去质子化。然而，在周围 (5-) 位引入甲氧基引起的支撑阻碍了溴（三氟甲基）喹啉的去质子化。与甲氧基相比，peri-Me

  DOI：

  10.1002/ejoc.200500728

文献信息

• Bromine as the Ortho-Directing Group in the Aromatic Metalation/Silylation of Substituted Bromobenzenes
  作者：Sergiusz Luliński、Janusz Serwatowski

  DOI：10.1021/jo034790h

  日期：2003.11.1

  The one-pot metalation/disilylation of selected bromobenzenes bearing electron-withdrawing substituents p-, m-, o-XC6H4Br (X = F, Cl, I, CN, CF3) using 2 equiv of lithium diisopropylamide (LDA) and 2 equiv of chlorotrimethylsilane (TMSCl) was investigated. The best results of disilylation were obtained for para-substituted bromobenzenes, but the regioselectivity of the reaction is strongly influenced by the ortho-directing power of the substituent. On the contrary, the disilylation of meta-substituted bromobenzenes was not efficient or even failed in some cases and hence monosilylated derivatives were isolated as major or sole products. Diverse reactivity was observed for ortho-substituted bromobenzenes, e.g., 2-bromobenzonitrile and 2-bromochlorobenzene, were converted into corresponding disilylated derivatives in a high and moderate yield, respectively, whereas 1-bromo-2-(trifluoromethyl)benzene underwent only monosilylation.
• Electrophilic ipso-iodination of silylated arylboronic acids
  作者：K. Durka、J. Górka、P. Kurach、S. Luliński、J. Serwatowski

  DOI：10.1016/j.jorganchem.2010.08.016

  日期：2010.11

  Silylated functionalized arylboronic acids were converted into corresponding iodinated arylboronic acids in good yields via the electrophilic ipso-desilylation effected with iodine chloride in refluxing CHCl3. Disilylated arylboronic acids were susceptible to diiodination. In addition, the structural characterization and reactivity of a novel sterically hindered ortho-silylated diarylborinic ester were reported. The potential of selected iodinated phenylboronic acids as monomers for the SuzukieMiyaura cross-coupling polymerization was demonstrated. (C) 2010 Elsevier B.V. All rights reserved.
• Relay Propagation of Crowding: The Trifluoromethyl Group as Both an Emitter and Transmitter of Steric Pressure
  作者：Manfred Schlosser、Fabrice Cottet、Christophe Heiss、Olivier Lefebvre、Marc Marull、Eric Masson、Rosario Scopelliti

  DOI：10.1002/ejoc.200500728

  日期：2006.2

  2-Bromo-4-(trifluoromethyl)pyridine, aza-analogous to the parent model arene 3-bromobenzotrifluoride, and both the benzo-azaanalogous 2-bromo-4-(trifluoromethyl)quinoline and its regioinverted isomer 4-bromo-2-(trifluoromethyl)quinoline are again readily deprotonated at the Br- and CF3-flanked positions. However, the buttressing caused by the introduction of a methoxy group at the peri-(5-)position impedes

  而锂 2,2,6,6-四甲基哌啶 (LITMP) 摘要。仅来自 3-溴代三氟化物的 4-位的质子，当在 N,N,N',N'',N''-五甲基二亚乙基三胺和叔丁醇钾存在下使用时，相同的碱基选择性地攻击 2-位（ qFaigl mixq)。1-Bromo-3,5-双(三氟甲基)苯也在2-位发生金属化，但[2-溴-4-(三氟甲基)苯基]硅烷根本不反应，显然被C-SiR3/ C-Br 支撑作用。2-Bromo-4-(trifluoromethyl)pyridine，氮杂类似于母体模型芳烃 3-溴三氟化物，以及苯并氮杂类似的 2-bromo-4-(trifluoromethyl)quinoline 及其区域转化异构体 4-bromo-2-(三氟甲基）喹啉再次在 Br 和 CF3 侧翼位置容易去质子化。然而，在周围 (5-) 位引入甲氧基引起的支撑阻碍了溴（三氟甲基）喹啉的去质子化。与甲氧基相比，peri-Me