4-bromo-2,5-bis(trimethylsilyl)benzonitrile | 632324-39-1

• 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: 4-bromo-2,5-bis(trimethylsilyl)benzonitrile
• CAS: 632324-39-1
• 化学式: C₁₃H₂₀BrNSi₂
• 分子量: 326.384
• InChiKey: BDFLAEIPZWTEPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.41
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-bromo-2,5-bis(trimethylsilyl)benzonitrile 在 正丁基锂 、 硼酸三甲酯 、 硫酸 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以66%的产率得到5-(三氟甲基)-2-(三甲基甲硅烷基)苯基硼酸
  参考文献：
  名称：

  Selective Generation of Lithiated Benzonitriles: the Importance of Reaction Conditions

  摘要：

  Lithiated benzonitriles can be generated in high yields from reactions of bromobenzonitriles with n-BuLi in THF under standard cryogenic conditions (ca. -70 degrees C) provided the reverse addition mode is employed. The resultant aryllithiums are fairly stable at temperatures up to -60 degrees C. The formation of lithiated benzonitriles via Br/Li exchange under normal addition mode conditions is plagued by deprotonation and extensive CN-addition reactions. The generation of related aryllithiums from disilylated bromobenzonitriles is comparatively less sensitive to reaction conditions.

  DOI：

  10.1021/jo8013808
• 作为产物：
  描述：

  三甲基氯硅烷 、 4-溴苯腈 在 lithium diisopropyl amide 、 硫酸 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以70%的产率得到4-bromo-2,5-bis(trimethylsilyl)benzonitrile
  参考文献：
  名称：

  具有结晶诱导的电化学发光发射增强的苯甲醚：合成，电化学和晶体学。

  摘要：

  首次使用两种新的苯并甲硅烷基苯进行了电化学诱导发光（ECL）的结晶诱导发射增强（CIEE）。与它们的溶液相比，两种苯并硅酮的薄膜的CIEE分别为24和16倍。通过绕线ECL光谱，X射线晶体结构分析，光致发光和DFT计算来检查CIEE-ECL的机理。该CIEE-ECL系统是完善的聚集诱发排放增强（AIEE）系统的补充。在结晶发色团中注意到了独特的分子间相互作用。建立了具有疏水性高的有机化合物的第一个异质ECL系统。

  DOI：

  10.1002/chem.202002647

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.
• Selective Generation of Lithiated Benzonitriles: the Importance of Reaction Conditions
  作者：Sergiusz Luliński、Katarzyna Zajac

  DOI：10.1021/jo8013808

  日期：2008.10.3

  Lithiated benzonitriles can be generated in high yields from reactions of bromobenzonitriles with n-BuLi in THF under standard cryogenic conditions (ca. -70 degrees C) provided the reverse addition mode is employed. The resultant aryllithiums are fairly stable at temperatures up to -60 degrees C. The formation of lithiated benzonitriles via Br/Li exchange under normal addition mode conditions is plagued by deprotonation and extensive CN-addition reactions. The generation of related aryllithiums from disilylated bromobenzonitriles is comparatively less sensitive to reaction conditions.
• Benzosiloles with Crystallization‐Induced Emission Enhancement of Electrochemiluminescence: Synthesis, Electrochemistry, and Crystallography
  作者：Liuqing Yang、Donghyun Koo、Jackie Wu、Jonathan M. Wong、Tyler Day、Ruizhong Zhang、Harshana Kolongoda、Kehan Liu、Jian Wang、Zhifeng Ding、Brian L. Pagenkopf

  DOI：10.1002/chem.202002647

  日期：2020.9.10

  Crystallization‐induced emission enhancement (CIEE) was demonstrated for the first time for electrochemilunimescence (ECL) with two new benzosiloles. Compared with their solution, the films of the two benzosiloles gave CIEE of 24 and 16 times. The mechanism of the CIEE‐ECL was examined by spooling ECL spectroscopy, X‐ray crystal structure analysis, photoluminescence, and DFT calculations. This CIEE‐ECL

  首次使用两种新的苯并甲硅烷基苯进行了电化学诱导发光（ECL）的结晶诱导发射增强（CIEE）。与它们的溶液相比，两种苯并硅酮的薄膜的CIEE分别为24和16倍。通过绕线ECL光谱，X射线晶体结构分析，光致发光和DFT计算来检查CIEE-ECL的机理。该CIEE-ECL系统是完善的聚集诱发排放增强（AIEE）系统的补充。在结晶发色团中注意到了独特的分子间相互作用。建立了具有疏水性高的有机化合物的第一个异质ECL系统。