1,3,5-tris(tribromomethyl)benzene

• 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: 1,3,5-tris(tribromomethyl)benzene
• 化学式: C₉H₃Br₉
• 分子量: 830.259
• InChiKey: IRHHXJBNVLOSMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  均三甲苯 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氯化碳 为溶剂， 反应 20.0h， 以79%的产率得到1,3,5-tris(tribromomethyl)benzene
  参考文献：
  名称：

  Photothermal Side-Chain Bromination of Methyl-, Dimethyl-, and Trimethylbenzenes withN-Bromosuccinimide

  摘要：

  采用钨丝灯在四氯化碳或苯溶剂中进行光热反应，实现了N-溴代琥珀酰亚胺对甲基苯、二甲基苯和三甲基苯的二溴化和三溴化。根据所用溶剂和苯环上取代基的不同，生成了二溴甲基芳烃和三溴甲基衍生物。在邻位无取代基的甲基苯的溴化反应中，生成了三溴甲基苯。另一方面，邻位取代的甲基苯生成了二溴甲基苯。通过三溴甲基苯在钨丝灯照射下的脱溴碳-碳偶联反应，生成了α,β-二溴-1,2-二芳基苯乙烯。

  DOI：

  10.1246/bcsj.67.1113

文献信息

• Improved process for side-chain bromination of alkyl-benzenes
  申请人：Helm AG

  公开号：EP1705168A1

  公开（公告）日：2006-09-27

  A process for the side-chain bromination of alkylbenzenes according to Formula (I) wherein R1 is C1-C6-alkyl; R2 is H or C1-C6-alkyl which can be unsubstituted or substituted by one or more cyano groups; R3 is H or C1-C6-alkyl which can be unsubstituted or substituted by one or more cyano groups; comprising the steps of (1) dissolving the compound of Formula (I) in a solvent which is a nonaromatic non-halogenated hydrocarbon which can be substituted by one or more cyano groups; (2) adding a bromination agent selected from the group consisting of Br2 and N-bromoimides to the solution; and optionally (3) agitating the mixture at a temperature within the range of from room temperature to reflux temperature.

  一种用于侧链溴化烷基苯的工艺，根据式（I）其中R1为C1-C6烷基；R2为H或C1-C6烷基，可以未取代或取代一个或多个氰基；R3为H或C1-C6烷基，可以未取代或取代一个或多个氰基；包括以下步骤：（1）将式（I）化合物溶解在一种溶剂中，该溶剂为一种非芳香族非卤代烃，可以取代一个或多个氰基；（2）向溶液中加入从Br2和N-溴代亚胺中选择的溴化试剂；以及可选的（3）在从室温到沸点温度范围内的温度下搅拌混合物。
• Process for side-chain bromination of alkylbenzenes
  申请人：Schulze Michael

  公开号：US20060217569A1

  公开（公告）日：2006-09-28

  A process for the side-chain bromination of alkylbenzenes according to Formula (I) wherein R 1 is C 1 -C 6 -alkyl; R 2 is H or C 1 -C 6 -alkyl which can be unsubstituted or substituted by one or more cyano groups; R 3 is H or C 1 -C 6 -alkyl which can be unsubstituted or substituted by one or more cyano groups; comprising the steps of (1) dissolving the compound of Formula (I) in a solvent which is a non-aromatic non-halogenated hydrocarbon which can be substituted by one or more cyano groups; (2) adding a bromination agent selected from the group consisting of Br 2 and N-bromoimides to the solution; and optionally (3) agitating the mixture at a temperature within the range of from room temperature to reflux temperature.

  一种用于侧链溴化烷基苯的制备的方法，根据式（I）中R1为C1-C6-烷基；R2为H或C1-C6-烷基，可以是未取代或取代一个或多个氰基；R3为H或C1-C6-烷基，可以是未取代或取代一个或多个氰基；包括以下步骤：（1）将式（I）化合物溶解在一种溶剂中，所述溶剂为一种非芳香族非卤代烃，可以被一个或多个氰基取代；（2）向溶液中加入从Br2和N-溴代亚胺中选择的溴化剂；可选地（3）在室温至沸点温度范围内搅拌混合物。
• Photothermal Side-Chain Bromination of Methyl-, Dimethyl-, and Trimethylbenzenes with<i>N</i>-Bromosuccinimide
  作者：Shuntaro Mataka、Guo-Bin Liu、Tsuyoshi Sawada、Masayoshi Kurisu、Masashi Tashiro

  DOI：10.1246/bcsj.67.1113

  日期：1994.4

  Tri- and dibromination of methyl-, dimethyl-, and trimethylbenzenes with N-bromosuccinimide were accomplished by photothermal reaction with a tungsten lamp in carbon tetrachloride or benzene. (Dibromomethyl)arenes and (tribromomethyl) derivatives were produced depending upon a solvent used and a substituent on the benzene ring. In the bromination of methylbenzenes without a substituent on the ortho-position, (tribromomethyl)benzenes were formed. On the other hand, ortho-substituted methylbenzenes gave (dibromomethyl)benzenes. α,β-Dibromo-1,2-diarylstilbenes were formed via the debrominative carbon–carbon coupling reaction of (tribromomethyl) benzenes upon irradiation with a tungsten lamp.

  采用钨丝灯在四氯化碳或苯溶剂中进行光热反应，实现了N-溴代琥珀酰亚胺对甲基苯、二甲基苯和三甲基苯的二溴化和三溴化。根据所用溶剂和苯环上取代基的不同，生成了二溴甲基芳烃和三溴甲基衍生物。在邻位无取代基的甲基苯的溴化反应中，生成了三溴甲基苯。另一方面，邻位取代的甲基苯生成了二溴甲基苯。通过三溴甲基苯在钨丝灯照射下的脱溴碳-碳偶联反应，生成了α,β-二溴-1,2-二芳基苯乙烯。
• Direct Formation of C−C Triple-Bonded Structural Motifs by On-Surface Dehalogenative Homocouplings of Tribromomethyl-Substituted Arenes
  作者：Qiang Sun、Xin Yu、Meiling Bao、Mengxi Liu、Jinliang Pan、Zeqi Zha、Liangliang Cai、Honghong Ma、Chunxue Yuan、Xiaohui Qiu、Wei Xu

  DOI：10.1002/anie.201801056

  日期：2018.4.3

  compounds directly into C−C triple‐bonded structural motifs by on‐surface dehalogenative homocoupling reactions. Concurrently, sp3‐hybridized carbon atoms are converted into sp‐hybridized ones, that is, an alkyl group is transformed into an alkynyl moiety. Moreover, we achieved the formation of dimer structures, one‐dimensional molecular wires, and two‐dimensional molecular networks on Au(111) surfaces

  表面合成显示出在构建新型纳米结构/纳米材料方面的巨大潜力，近年来对此进行了深入研究。炔基支架的形成为制造新兴的碳纳米结构提供了一条重要途径，包括碳炔，石墨烯和石墨二炔，它们具有易受化学作用的杂化碳原子。在这里，我们设计并合成了一个三溴甲基取代的化合物。通过结合使用高分辨率扫描隧道显微镜，非接触原子力显微镜和密度泛函理论计算，我们证明了通过表面脱卤将这些化合物直接转化为CC三键结构基序是可行的均偶联反应。同时，sp 3杂交的碳原子被转化为sp杂交的碳原子，即烷基被转化为炔基部分。此外，我们在Au（111）表面上实现了二聚体结构，一维分子线和二维分子网络的形成，这应激发对二维石墨烯结构的进一步研究。
• Haloaluminoxane compositions, their preparation, and their use in catalysis
  申请人：Sangokoya A. Samuel

  公开号：US20050143254A1

  公开（公告）日：2005-06-30

  Novel haloaluminoxane compositions have been formed. The halogen is fluorine, chlorine, and/or bromine, and the amount of halogen atoms present in said composition is in the range of about 0.5 mole % to about 15 mole % relative to aluminum atoms.

  新型卤铝氧烷组合物已经形成。卤素是氟、氯和/或溴，相对于铝原子，所述组合物中卤素原子的含量在约 0.5 摩尔%至约 15 摩尔%的范围内。