2,5-二溴-3-苯基噻吩 | 19698-46-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 2,5-二溴-3-苯基噻吩
• 中文别名: 2,5-二溴3-苯噻吩
• 英文名称: 2,5-dibromo-3-phenylthiophene
• CAS: 19698-46-5
• 化学式: C₁₀H₆Br₂S
• 分子量: 318.032
• InChiKey: JYNOXEBITOGCMQ-UHFFFAOYSA-N

物化性质

• 熔点：
  35-39 °C(lit.)
• 沸点：
  291.9±35.0 °C(Predicted)
• 密度：
  1.801±0.06 g/cm3(Predicted)
• 闪点：
  230 °F
• 稳定性/保质期：
  按规定使用，这种物质不会分解，并且能够避免与氧化物反应。

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 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

安全信息

• WGK Germany：
  3
• 储存条件：
  2-8°C冷藏，存于密封容器中，并置于干燥处。

制备方法与用途

用途：用于制备导电聚合物的前体。

反应信息

• 作为反应物：
  描述：

  2,5-二溴-3-苯基噻吩 在 溴 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以81%的产率得到2,4,5-tribromo-3-phenylthiophene
  参考文献：
  名称：

  Rigid-Core Fluorescent Oligothiophene-S,S-dioxide Isothiocyanates. Synthesis, Optical Characterization, and Conjugation to Monoclonal Antibodies

  摘要：

  In this paper we report the synthesis of a new class of fluorescent thiophene-based isothiocyanates containing a 3,5-disubstituted dithieno[3,2-b:2',3'-d]thiophene-4,4-dioxide moiety as the rigid core, using the palladium-catalyzed cross-coupling reaction of aryl stannanes with aryl bromides (Stille coupling). By changing the molecular structure through the progressive addition of thienylene or phenylene units, light emission from blue to orange was obtained. Photoluminescence quantum yields ranged from 0.65 to 0.90 for blue and green light emitters to 0.10-0.35 for yellow and orange ones. Optically and chemically stable fluorescent bioconjugates were prepared by spontaneous reaction of the isothiocyanates with monoclonal antibodies anti-CD3 and anti-CD8 in slightly basic solutions.

  DOI：

  10.1021/jo026298o
• 作为产物：
  描述：

  3-苯基噻吩 在 甲醇 、 四丁基溴化铵 、 溴 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到2,5-二溴-3-苯基噻吩
  参考文献：
  名称：

  New and efficient access to 3-substituted 2,5-dibromothiophenes. Consecutive nickel-catalyzed electrochemical conversion to thienylzinc species

  摘要：

  我们已经通过电化学方法和一种原创的溴化程序实现了3取代噻吩锌试剂的逐步合成。对于几个化合物，3-溴噻吩是起始底物，它根据最近开发的电化学程序进行了功能化。在锌盐存在下，对得到的3取代2,5-二溴噻吩进行镍催化的电化学还原，使得单噻吩锌物种以良好的产率形成。关于该反应的选择性，我们在电化学合成有规聚噻吩的背景下进行了讨论。

  DOI：

  10.1039/b006748m

文献信息

• Synthesis, characterization, and electrogenerated chemiluminescence of phenyl-substituted, phenyl-annulated, and spirofluorenyl-bridged oligothiophenes
  作者：Ullrich Mitschke、Peter Bäuerle

  DOI：10.1039/b006553f

  日期：——

  To overcome the insolubility of higher oligothiophenes and simultaneously to enhance their processability with respect to an application in molecularly doped organic light-emitting devices (OLEDs) we synthesized phenyl-substituted, phenyl-annulated, and spirofluorenyl-bridged oligothiophenes 1–5. Significantly improved solubilities in polar solvents of up to three orders of magnitude were found and their optical and electrochemical properties were investigated in solution. Reflecting small conformational changes and the almost complete electronic separation of the substituents, phenyl substitution and the introduction of a spiro core by bridging the central bithienyl unit only slightly affected optical and redox properties in comparison to the unmodified oligothiophenes (6–8). In contrast, the presence of an isothianaphthene (benzo[c]thiophene) unit in the oligomeric chain led to a distinct approximation of the frontier orbitals and consequently to a red-shift of both absorption and fluorescence. Finally, we demonstrated the applicability of some oligomers as dopants for OLEDs by electrogenerated chemiluminescence (ECL).

  为了克服高阶寡聚噻吩的不溶性并同时提高它们在分子掺杂有机发光二极管(OLEDs)应用中的可加工性,我们合成了苯基取代的、苯基稠合的和螺芴基桥连的寡聚噻吩1-5。研究发现这些化合物在极性溶剂中的溶解度显著提高了最多三个数量级,并对它们在溶液中的光学和电化学性质进行了研究。与未修饰的寡聚噻吩(6-8)相比,苯基取代和通过桥连中心联噻吩基团引入螺环核心仅略微影响了光学和氧化还原性质,这反映了构象的微小变化和取代基之间几乎完全的电子分离。相比之下,寡聚物链中异噻萘(苯并[c]噻吩)单元的存在导致前沿轨道的明显趋近,因此吸收和荧光都发生红移。最后,我们通过电化学发光(ECL)证明了某些寡聚物作为OLED掺杂剂的适用性。
• Rewiring Chemistry: Algorithmic Discovery and Experimental Validation of One-Pot Reactions in the Network of Organic Chemistry
  作者：Chris M. Gothard、Siowling Soh、Nosheen A. Gothard、Bartlomiej Kowalczyk、Yanhu Wei、Bilge Baytekin、Bartosz A. Grzybowski

  DOI：10.1002/anie.201202155

  日期：2012.8.6

  Computational algorithms are used to identify sequences of reactions that can be performed in one pot. These predictions are based on over 86 000 chemical criteria by which the putative sequences are evaluated. The “raw” algorithmic output is then validated experimentally by performing multiple two‐, three‐, and even four‐step sequences. These sequences “rewire” synthetic pathways around popular and/or

  计算算法用于识别可以在一锅中进行的反应序列。这些预测是基于超过86000个化学标准来评估推定序列的。然后，通过执行多个两步，三步甚至四步序列，对“原始”算法的输出进行实验验证。这些序列围绕流行和/或重要的小分子“重新合成”合成途径。
• Multicyclic compounds and methods of use thereof
  申请人：Shao Liming

  公开号：US08710245B2

  公开（公告）日：2014-04-29

  Provided herein are multicyclic compounds, methods of their synthesis, pharmaceutical compositions comprising the compounds, and methods of their use. The compounds provided herein are useful for the treatment, prevention, and/or management of various neurological disorders, including but not limited to, psychosis and schizophrenia.

  本文提供多环化合物、其合成方法、包含该化合物的药物组合物以及使用该化合物的方法。所提供的化合物对于治疗、预防和/或管理各种神经系统疾病，包括但不限于精神病和精神分裂症具有用途。
• MULTICYCLIC COMPOUNDS AND METHODS OF USE THEREOF
  申请人：Shao Liming

  公开号：US20130109677A1

  公开（公告）日：2013-05-02

  Provided herein are multicyclic compounds, methods of their synthesis, pharmaceutical compositions comprising the compounds, and methods of their use. The compounds provided herein are useful for the treatment, prevention, and/or management of various neurological disorders, including but not limited to, psychosis and schizophrenia.

  本文提供了多环化合物，其合成方法，包括该化合物的药物组合物，以及使用方法。本文提供的化合物对于治疗、预防和/或管理各种神经系统疾病非常有用，包括但不限于精神病和精神分裂症。
• [EN] MULTICYCLIC COMPOUNDS AND METHODS OF USE THEREOF<br/>[FR] COMPOSÉS MULTICYCLIQUES ET LEURS PROCÉDÉS D'UTILISATION
  申请人：SUNOVION PHARMACEUTICALS INC

  公开号：WO2011069063A3

  公开（公告）日：2011-10-20