1,3-bis(4-bromophenyl)-1,3-dihydrobenzimidazol-2-one | 372942-52-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 1,3-bis(4-bromophenyl)-1,3-dihydrobenzimidazol-2-one
• 英文别名: 1,3-bis(4-bromophenyl)-1,3-dihydro-2H-benzo[d]imidazol-2-one；1,3-Bis(4-bromophenyl)benzimidazol-2-one
• CAS: 372942-52-4
• 化学式: C₁₉H₁₂Br₂N₂O
• 分子量: 444.125
• InChiKey: KVTLPMZBJRDUKK-UHFFFAOYSA-N

物化性质

• 沸点：
  548.1±60.0 °C(Predicted)
• 密度：
  1.722±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-苯基-4-联苯胺 、 1,3-bis(4-bromophenyl)-1,3-dihydrobenzimidazol-2-one 在 tris-(dibenzylideneacetone)dipalladium(0) 、 三叔丁基膦 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 9.5h， 生成 1,3-bis[4-(N-(4-phenylphenyl)anilino)phenyl]benzimidazol-2-one
  参考文献：
  名称：

  ORGANIC COMPOUND, CHARGE-TRANSPORTING MATERIAL, COMPOSITION FOR CHARGE-TRANSPORTING MATERIAL AND ORGANIC ELECTROLUMINESCENT DEVICE

  摘要：

  公开号：

  EP1956008B1
• 作为产物：
  描述：

  2-羟基苯并咪唑 、 1,4-二溴苯 在 copper(l) iodide 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以28%的产率得到1,3-bis(4-bromophenyl)-1,3-dihydrobenzimidazol-2-one
  参考文献：
  名称：

  o,p-Polyaniline:  A New Form of a Classic Conducting Polymer

  摘要：

  A new o-PANI-co-p-PANI copolymer was prepared in order to allow for the introduction of solubilizing and function-enhancing substituents on the conducting polymer backbone without concomitant loss of conductivity. An urea-protected trimeric aniline macromonomer with para-ortho-para connectivity and bromine end groups was condensed using palladium catalysis with a di-BOC-protected trimeric aniline comonomer with all para connectivity and amine end groups to give 5p,o-PANI. The new polymer has a repeat unit consisting of five para-substituted aniline rings for every one ortho-substituted aniline ring. The regioregularity of 5p,o-PANI {M-n = 14 000, GPC in NMP, polystyrene standards) was established using H-1 NMR, C-13{H} NMR, and IR spectroscopy. Analogous with p-PANI, the 5p,o-PANI exhibited three distinct oxidation states. The conductivity of blends of 5p,o-PANI and PVC was on the same order of magnitude as the conductivity of PANI films prepared under the same conditions.

  DOI：

  10.1021/ma021343f

文献信息

• Chan-Lam cross-coupling reaction based on the Cu 2 S/TMEDA system
  作者：Kateřina Janíková、Lukáš Jedinák、Tereza Volná、Petr Cankař

  DOI：10.1016/j.tet.2017.12.042

  日期：2018.2

  several pinacol or neopentylglycol boronates indicated further potential of the catalyst. The reaction conditions tolerate the hydroxyl and bromo functional groups. The catalytic system also enables to synthesize the mono-N-substituted anilines from primary aliphatic amines. However, the two model compounds for the secondary and aromatic amines, piperidine and aniline, do not react. Two sterically demanding

  基于Chan-Lam交叉偶联反应，开发了一种基于使用稳定铜（I）源的现成Cu 2 S / TMEDA系统的催化剂。用1 H-苯并[ d ]咪唑-2（3 H）-1，1 H-苯并[ d ]咪唑和1 H-咪唑以及缺电子，富电子和在室温下，在大气氧的存在下，对空间需求量高的硼酸，以中等至极好的收率得到交叉偶联的产物。另外，1 H-苯并[ d]的偶联反应]咪唑与几种频哪醇或新戊二醇硼酸酯表明该催化剂的进一步潜力。反应条件容许羟基和溴官能团。该催化体系还能够由伯脂族胺合成单-N-取代的苯胺。但是，仲胺和芳族胺的两种模型化合物哌啶和苯胺不会反应。两个空间要求的产品与受限Ç N键的旋转，通过将合成的Ñ 1的-arylation ħ -苯并[ d ]咪唑-2（3 H ^） -酮与ö-甲苯磺酸，能够确认由Chan-Lam交叉偶联反应制得的阻转异构体。此外，已经报道了一锅Chan-Lam和Suzuki-Miyaura反应的例子。
• US8022617B2
  申请人：——

  公开号：US8022617B2

  公开（公告）日：2011-09-20
• ORGANIC COMPOUND, CHARGE-TRANSPORTING MATERIAL, COMPOSITION FOR CHARGE-TRANSPORTING MATERIAL AND ORGANIC ELECTROLUMINESCENT DEVICE
  申请人：Mitsubishi Chemical Corporation

  公开号：EP1956008B1

  公开（公告）日：2012-03-28
• <i>o,p-</i>Polyaniline:  A New Form of a Classic Conducting Polymer
  作者：Rachel E. Ward、Tara Y. Meyer

  DOI：10.1021/ma021343f

  日期：2003.6.1

  A new o-PANI-co-p-PANI copolymer was prepared in order to allow for the introduction of solubilizing and function-enhancing substituents on the conducting polymer backbone without concomitant loss of conductivity. An urea-protected trimeric aniline macromonomer with para-ortho-para connectivity and bromine end groups was condensed using palladium catalysis with a di-BOC-protected trimeric aniline comonomer with all para connectivity and amine end groups to give 5p,o-PANI. The new polymer has a repeat unit consisting of five para-substituted aniline rings for every one ortho-substituted aniline ring. The regioregularity of 5p,o-PANI M-n = 14 000, GPC in NMP, polystyrene standards) was established using H-1 NMR, C-13H} NMR, and IR spectroscopy. Analogous with p-PANI, the 5p,o-PANI exhibited three distinct oxidation states. The conductivity of blends of 5p,o-PANI and PVC was on the same order of magnitude as the conductivity of PANI films prepared under the same conditions.