(9ci)-1-(3-吡啶)-1H-苯并咪唑 | 25660-38-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: (9ci)-1-(3-吡啶)-1H-苯并咪唑
• 中文别名: 1H-苯并咪唑，1-（3-吡啶基）-（9CI）；(9CI)-1-(3-吡啶)-1H-苯并咪唑
• 英文名称: 1-(pyridin-3-yl)-1H-benzo[d]imidazole
• 英文别名: N-(3-pyridinyl)benzimidazole；1-(3-pyridyl)-benzimidazol；1-(3-pyridyl)benzimidazole；1-pyridin-3-yl-1H-benzoimidazole；1-β-Pyridyl-benzimidazol；1-pyridin-3-ylbenzimidazole
• CAS: 25660-38-2
• 化学式: C₁₂H₉N₃
• 分子量: 195.224
• InChiKey: KJBHWIMSQSVPME-UHFFFAOYSA-N

物化性质

• 熔点：
  89-91 °C
• 沸点：
  394.5±44.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  (9ci)-1-(3-吡啶)-1H-苯并咪唑 在 silver(l) oxide 作用下， 以 四氢呋喃 、 乙二醇乙醚 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  N-Heterocyclic Carbenes: Versatile Second Cyclometalated Ligands for Neutral Iridium(III) Heteroleptic Complexes

  摘要：

  With 2-(2,4-difluorophenyl)pyridine (dfppy) as the first cyclometalated ligand and different monoanionic N-heterocyclic carbenes (NHCs) as the second cyclometalated ligands, 16 blue or greenish-blue neutral iridium(III) phosphorescent complexes, (dfppy)(2)Ir(NHC), were synthesized efficiently. The obtained Ir(III) complexes display typical phosphorescence of 455-485 nm with quantum yields up to 0.73. By modifying the phenyl moiety in the NHCs with electron-withdrawing substituents (e.g., -F or -CF3) or replacing it with N-heteroaromatic rings (pyridine or pyrimidine), the HOMO-LUMO gaps are broadened, and the emissions shift to the more blue region accordingly. Furthermore, to extend the application scope of NHCs as the second cyclometalated ligands, five other Ir(III) complexes from blue to red were synthesized with different first cyclometalated ligands. Finally, the organic light-emitting diodes using one blue emitter exhibit a maximum current efficiency of 37.83 cd A(-1), an external quantum efficiency of 10.3%, and a maximum luminance of 8709 cd m(-2). Our results demonstrate that NHCs as the second cyclometalated ligands are good candidates for the achievement of efficient phosphorescent Ir-III complexes and corresponding devices.

  DOI：

  10.1021/ic501949h
• 作为产物：
  描述：

  苯并咪唑 、 3-吡啶硼酸新戊二醇酯 在 copper(I) sulfide 、 四甲基乙二胺 作用下， 以 甲醇 为溶剂， 以90 %的产率得到(9ci)-1-(3-吡啶)-1H-苯并咪唑
  参考文献：
  名称：

  基于Cu 2 S / TMEDA系统的Chan-Lam交叉偶联反应

  摘要：

  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。

  DOI：

  10.1016/j.tet.2017.12.042

文献信息

• Highly efficient and practical phosphoramidite–copper catalysts for amination of aryl iodides and heteroaryl bromides with alkylamines and N(H)-heterocycles
  作者：Zhanjin Zhang、Jincheng Mao、Di Zhu、Fan Wu、Huilin Chen、Boshun Wan

  DOI：10.1016/j.tet.2006.02.062

  日期：2006.5

  A highly efficient copper-catalyzed system using phosphoramidite as ligands was applied to N-arylation of alkylamines and N(H)-heterocycles with aryl iodides and heteroaryl bromides. The reactions were carried out in relative mild conditions and good to excellent yields were obtained.

  使用亚磷酰胺作为配体的高效铜催化体系被用于烷基胺和N（H）-杂环与芳基碘化物和杂芳基溴化物的N-芳基化反应。反应在相对温和的条件下进行，并获得了良好的产率。
• Synthesis of Aza-Fused Polycyclic Quinolines via Double CH Bond Activation
  作者：Ji-Rong Huang、Lin Dong、Bo Han、Cheng Peng、Ying-Chun Chen

  DOI：10.1002/chem.201201207

  日期：2012.7.16

  but efficient: Aza‐fused polycyclic quinolines were efficiently assembled through rhodium(III)‐based direct double CH activation of N‐aryl azoles followed by cyclization with alkynes without heteroatom‐assisted chelation. Copper(II) acetate, aside from acting as an oxidant, could also play an important role in the CH activation process.

  简单但有效：氮杂稠合的多环喹啉通过基于铑（III）的N-芳基唑的直接双CH活化，然后与炔烃环化而没有杂原子辅助的螯合作用而得到有效组装。乙酸铜（II）除了起氧化剂的作用外，在CH活化过程中也可能起重要作用。
• Ligand-free copper-catalysed coupling reaction of heteroaryl bromides with imidazole and benzimidazole
  作者：Xiang-Mei Wu、Yan Wang

  DOI：10.3184/030823409x12506792542864

  日期：2009.9

  The synthesis of N-heteroarylimidazoles by coupling heteroaryl bromides with imidazole or benzimidazole under relatively mild conditions using the stable and readily available copper(II) acetate as catalyst and cesium carbonate as base is reported to give products in moderate to good yields.

  据报道，在相对温和的条件下，以稳定易得的醋酸铜（II）为催化剂，以碳酸铯为碱，通过将杂芳基溴化物与咪唑或苯并咪唑偶联合成 N-杂芳基咪唑，可获得中等至良好收率的产品。
• Copper promoted CN and CO bond cross-coupling with phenyl and pyridylboronates
  作者：Dominic M.T. Chan、Kevin L. Monaco、Renhua Li、Damien Bonne、Charles G. Clark、Patrick Y.S. Lam

  DOI：10.1016/s0040-4039(03)00739-1

  日期：2003.5

  Acyclic and cyclic esters, as well as anhydride (boroxine) of phenylboronic acids are efficient phenylating agents in copper promoted C-N and C-O bond cross-coupling reactions. The first successful C-N cross-coupling of a heterocyclic boronate with heteroarenes, such as indazole, has been demonstrated. (C) 2003 Elsevier Science Ltd. All rights reserved.
• [EN] QUINOLONES USEFUL AS INDUCIBLE NITRIC OXIDE SYNTHASE INHIBITORS<br/>[FR] QUINOLONES UTILES EN TANT QU'INHIBITEURS DE L'OXYDE NITRIQUE SYNTHASE INDUCTIBLE
  申请人：KALYPSYS INC

  公开号：WO2007117778A9

  公开（公告）日：2009-05-22