5,5'-dibromo-3,3'-dimethyl-2,2'-bithiophene | 127236-45-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 5,5'-dibromo-3,3'-dimethyl-2,2'-bithiophene
• 英文别名: 5-bromo-2-(5-bromo-3-methylthiophen-2-yl)-3-methylthiophene
• CAS: 127236-45-7
• 化学式: C₁₀H₈Br₂S₂
• 分子量: 352.114
• InChiKey: MPDYYPROBCGOFV-UHFFFAOYSA-N

物化性质

• 熔点：
  58 °C
• 沸点：
  313.7±37.0 °C(Predicted)
• 密度：
  1.772±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,5'-dibromo-3,3'-dimethyl-2,2'-bithiophene 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 、 偶氮二异丁腈 作用下， 以 苯 为溶剂， 以78%的产率得到5,5'-dibromo-3,3'-bis(bromomethyl)-2,2'-bithiophene
  参考文献：
  名称：

  Designing conducting polymer-based sensors: selective ionochromic response in crown ether-containing polythiophenes

  摘要：

  DOI：

  10.1021/ja00078a090
• 作为产物：
  描述：

  3-甲基噻吩 在 N-溴代丁二酰亚胺(NBS) 、 [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](triphenylphosphine)nickel(II) dichloride 、 乙基氯化镁 作用下， 生成 5,5'-dibromo-3,3'-dimethyl-2,2'-bithiophene
  参考文献：
  名称：

  Nosyl (2-Nitrobenzenesulfonyl) Annulation Strategy toward Winding Vine-Shaped Bithiophenes

  摘要：

  Winding vine-shaped bithiophene was synthesized through the nosyl (2-nitrobenzenesulfonyl) cyclization protocol. The reaction of bithiophene bearing bromomethyl groups at the 3,3'-positions with nosylated 1,2-ethylenediamine in the presence of potassium carbonate afforded the annulated product in excellent yield. The obtained bithiophene was found to contain a 10-membered ring, which was confirmed by X-ray analysis. The related nosyldiamine bearing a tri- or tetramethylene group also reacted in a similar manner, affording an 11- or 12-membered macrocycle, respectively.

  DOI：

  10.1021/acs.joc.8b02382

文献信息

• SYNTHESIS, SOME SPECTROSCOPIC AND ELECTROCHEMICAL INVESTIGATIONS ON NOVEL MONOMERIC AND POLYMERIC ACETYLENE SUBSTITUTED THIOPHENE MONOMERS AND POLYMERS
  作者：Hans Zimmer、Kobkul Sudsuansri、Harry B. Mark、Bernd Ziegler

  DOI：10.1080/10426509708043516

  日期：1997.3.1

  Abstract Acetylene substituted thiophenes of the following types were synthesized: Ar-[tbnd]-Ar-[tbnd]-Ar, Ar′-[tbnd]-Ar′-[tbnd]Ar′, Ar-[tbnd]-Ar′-[tbnd]-Ar, Ar′-[tbnd]-Ar-Ar-[tbnd]-Ar′, Ar-[tbnd]-Ar-Ar′-[tbnd]-Ar′These monomen were polymerized to the corresponding polymers. The UV-spectra and their oxidation potentials were determined. Attempts to correlate these two properties will be reported. The

  摘要 合成了以下类型的乙炔取代噻吩：Ar-[tbnd]-Ar-[tbnd]-Ar、Ar'-[tbnd]-Ar'-[tbnd]Ar'、Ar-[tbnd]-Ar'- [tbnd]-Ar、Ar'-[tbnd]-Ar-Ar-[tbnd]-Ar'、Ar-[tbnd]-Ar-Ar'-[tbnd]-Ar'将这些单体聚合成相应的聚合物。测定了紫外光谱和它们的氧化电位。将报告将这两个属性相关联的尝试。相应的聚合物具有相对低的分子量，并且在掺杂和碘掺杂状态下都是非导体。
• Solvent-Free, Microwave-Assisted Synthesis of Thiophene Oligomers via Suzuki Coupling
  作者：Manuela Melucci、Giovanna Barbarella、Giovanna Sotgiu

  DOI：10.1021/jo026269d

  日期：2002.12.1

  The purpose of this study was to obtain a rapid, efficient, and environmentally friendly methodology for the synthesis of highly pure thiophene oligomers. The solvent-free, microwave-assisted coupling of thienyl boronic acids and esters with thienyl bromides, using aluminum oxide as the solid support, allowed us to rapidly check the reaction trends on changing times, temperature, catalyst, and base

  这项研究的目的是获得一种快速，高效和环保的方法来合成高纯度的噻吩低聚物。噻吩基硼酸和酯与噻吩基溴的无溶剂微波辅助偶联，使用氧化铝作为固体载体，使我们能够快速检查反应时间，温度，催化剂和碱的变化趋势，并轻松优化实验获得公允价值目标产品的条件。该方法为制备可溶性噻吩低聚物提供了新颖，通用且非常快速的途径。因此，例如，通过2-溴-2,2'-联噻吩与双（频哪醇）二硼的反应，在6分钟内获得了四噻吩（分离产率为65％），而二噻吩并噻吩与噻吩基硼酸的反应在11分钟内获得了喹噻吩（分离产率为74％）。报道了新的手性2，2′-联噻吩的合成。对某些反应副产物的详细分析使我们能够阐明反应机理的几个方面。虽然证明使用微波非常方便常规噻吩基部分之间的偶联，但对于噻吩基环与噻吩基-S，S-二氧化物部分的偶联而言却并非如此。实际上，在这种情况下，由于竞争性的，加速的Diels-Alder反应可提供多种缩合产物，因此以低
• New Conjugated Oligothiophenes Containing the Unique Arrangement of Internal Adjacent [All]-<i>S,S</i>-Oxygenated Thiophene Fragments
  作者：Shay Potash、Shlomo Rozen

  DOI：10.1002/chem.201203936

  日期：2013.4.22

  obtaining conjugated oligothiophene‐containing molecules with narrower HOMO–LUMO gaps and higher oxidation and reduction potentials is the subject of this study. Molecules containing the bithiophene tetraoxide (2) and the terthiophene hexaoxide (3) moieties were prepared and studied. They were obtained by transferring oxygen atoms to the corresponding dibromo oligothiophenes with the HOF⋅CH3CN complex and then

  寻求获得具有更窄的HOMO-LUMO间隙和更高的氧化还原电位的共轭含低聚噻吩的分子是本研究的主题。制备并研究了包含四联噻吩（2）和六噻吩（3）部分的分子。他们被氧原子转移到与所述HOF相应二溴低聚噻吩得到⋅ CH 3CN络合物，然后将它们与噻吩或乙炔锡衍生物交叉偶联。产品的光物理和电化学研究表明，与任何其他排列的低聚噻吩（包括各种[所有] -S，S-氧代噻吩衍生物）相比，这种特殊类型的混合噻吩的特征是明显更小的前沿轨道间隙以及更高的氧化和还原电势。
• Designing conducting polymer-based sensors: selective ionochromic response in crown ether-containing polythiophenes
  作者：Michael J. Marsella、Timothy M. Swager

  DOI：10.1021/ja00078a090

  日期：1993.12
• Pham, Chiem Van; Burkhardt, A.; Shabana, R., Phosphorus, Sulfur and Silicon and the Related Elements, 1989, vol. 46, p. 153 - 168
  作者：Pham, Chiem Van、Burkhardt, A.、Shabana, R.、Cunningham, David D.、Mark, Harry B.、Zimmer, Hans

  DOI：——

  日期：——