2-bromo-5-(4-bromophenyl)thiophene | 183619-15-0

• 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: 2-bromo-5-(4-bromophenyl)thiophene
• CAS: 183619-15-0
• 化学式: C₁₀H₆Br₂S
• 分子量: 318.032
• InChiKey: YXENZJCLORDOKW-UHFFFAOYSA-N

物化性质

• 沸点：
  338.4±27.0 °C(Predicted)
• 密度：
  1.801±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-bromo-5-(4-bromophenyl)thiophene 、 咔唑 在 potassium phosphate 、 copper(l) iodide 、 (1S,2S)-(+)-1,2-环己二胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以64.9%的产率得到9-(4-(5-(9H-carbazol-9-yl)thiophen-2-yl)phenyl)-9H-carbazole
  参考文献：
  名称：

  Novel Organic Semiconductors Based on Phenyl and Phenylthienyl Derivatives for Organic Thin-Film Transistors

  摘要：

  New phenyl and phenylthienyl derivatives end-functionalized with carbazole and a-carboline, 9-(4(9-H-carbazol-9-yl)phenyl)-9H-carbazole, 9-(4-(9H-carbazol-9-yl)phenyl)-9H-pyrido[2,3-b]indole, 9(3-(9H-carbazol-9-yl)pheny1)-9H-carbazole, 9-(3-(9H-carbazol-9-yl)pheny1)-9H-pyrido[2,3-b]indole, 9-(4-(5-(9H-carbazol-9-yl)thiophen-2-yl)phenyl)-9H-carbazole, and 9-(3-(5-(9H-carbazol-9-yl) thiophen-2-yl)phenyl)-9H-carbazole were synthesized and characterized as organic semiconductors for organic thin-film transistors (OTFTs). Most compounds exhibited p-channel characteristics with carrier mobility as high as 1.7 x 10(-5) cm(2)Ns and a current on/off ratio of 10(2)-10(4) for top-contact/bottom-gate OTFT devices.

  DOI：

  10.1166/jnn.2016.10748
• 作为产物：
  描述：

  2-(4-溴苯基)噻吩 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以99.7%的产率得到2-bromo-5-(4-bromophenyl)thiophene
  参考文献：
  名称：

  Novel Organic Semiconductors Based on Phenyl and Phenylthienyl Derivatives for Organic Thin-Film Transistors

  摘要：

  New phenyl and phenylthienyl derivatives end-functionalized with carbazole and a-carboline, 9-(4(9-H-carbazol-9-yl)phenyl)-9H-carbazole, 9-(4-(9H-carbazol-9-yl)phenyl)-9H-pyrido[2,3-b]indole, 9(3-(9H-carbazol-9-yl)pheny1)-9H-carbazole, 9-(3-(9H-carbazol-9-yl)pheny1)-9H-pyrido[2,3-b]indole, 9-(4-(5-(9H-carbazol-9-yl)thiophen-2-yl)phenyl)-9H-carbazole, and 9-(3-(5-(9H-carbazol-9-yl) thiophen-2-yl)phenyl)-9H-carbazole were synthesized and characterized as organic semiconductors for organic thin-film transistors (OTFTs). Most compounds exhibited p-channel characteristics with carrier mobility as high as 1.7 x 10(-5) cm(2)Ns and a current on/off ratio of 10(2)-10(4) for top-contact/bottom-gate OTFT devices.

  DOI：

  10.1166/jnn.2016.10748

文献信息

• Gold-Catalyzed Oxidative Coupling of Arylsilanes and Arenes: Origin of Selectivity and Improved Precatalyst
  作者：Liam T. Ball、Guy C. Lloyd-Jones、Christopher A. Russell

  DOI：10.1021/ja408712e

  日期：2014.1.8

  substitution of the arylsilane and the arene by Au(III) precedes product-forming reductive elimination and subsequent cycle-closing reoxidation of the metal. Despite the fundamental mechanistic similarities between the two auration events, high selectivity is observed for heterocoupling (C-Si then C-H auration) over homocoupling of either the arylsilane or the arene (C-Si then C-Si, or C-H then C-H auration);

  已经研究了金催化芳烃与芳基三甲基硅烷偶联的机制，采用改进的预催化剂 (thtAuBr3) 促进动力学分析。结合线性自由能关系、动力学同位素效应和化学计量实验，数据支持了一种涉及 Au(I)/Au(III) 氧化还原循环的机制，其中芳基硅烷和芳烃被 Au( III) 先于形成产物的还原消除和随后的金属循环闭合再氧化。尽管这两个 auration 事件之间的基本机制相似，但观察到杂偶联（C-Si 然后 CH auration）比芳基硅烷或芳烃的均偶联（C-Si 然后 C-Si，或 CH 然后 CH auration）具有高选择性；这种化学选择性源于每个亲电取代的产物决定基本步骤的差异。反应的周转限制步骤涉及到芳烃 π 复合物途中的缔合取代。讨论了这种洞察力对方法实施的影响。
• Site-selective mono-oxidative addition of active zinc into carbon–bromine bond of dibrominated-thiophenes: preparation of thienylzinc reagents and their applications
  作者：Hye-Soo Jung、Hyun-Hee Cho、Seung-Hoi Kim

  DOI：10.1016/j.tetlet.2012.12.024

  日期：2013.2

  A facile protocol for the preparation of 3-bromo-2-thienylzinc bromide A and 5-bromo-2-thienylzinc bromide B has been developed. It has been successfully accomplished by a site-selective oxidative addition of active zinc into a chemically pseudo-equivalent or equivalent carbon-bromine bond, respectively. The subsequent cross-coupling reactions of the organozincs were also successfully carried out under mild conditions providing the corresponding products in moderate to high yields. (C) 2012 Elsevier Ltd. All rights reserved.