3,5-dibromo-2-(trimethylsilyl)thiophene | 112051-54-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 3,5-dibromo-2-(trimethylsilyl)thiophene
• 英文别名: (3,5-Dibromo-thiophen-2-yl)-trimethyl-silane；(3,5-dibromothiophen-2-yl)-trimethylsilane
• CAS: 112051-54-4
• 化学式: C₇H₁₀Br₂SSi
• 分子量: 314.116
• InChiKey: VSWWXEAEODXCJK-UHFFFAOYSA-N

物化性质

• 沸点：
  95-97 °C(Press: 2 Torr)
• 密度：
  1?+-.0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.82
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  3,5-dibromo-2-(trimethylsilyl)thiophene 在 正丁基锂 、 间氯过氧苯甲酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 2,5-bis(trimethylsilyl)thiophene 1,1-dioxide
  参考文献：
  名称：

  2,5-二溴噻吩的区域特异性甲硅烷基化：再研究

  摘要：

  LDA将2,5-二溴噻吩与随后的甲硅烷基化反应按照卤素舞机理在区域上进行区域特异性反应，从而生成3,5-二溴-2-三甲基甲硅烷基噻吩或3,4-二溴-2,5-双（三甲基甲硅烷基）噻吩，具体取决于试剂的比例。该反应的结果通过后一种化合物进一步化学转化为2，5-双（三甲基甲硅烷基）噻吩和2，5-双（三甲基甲硅烷基）噻吩-1，1-二氧化物来证实。在砜的情况下，通过1 H，13 C和29 Si NMR以及X射线分析来确定所获得的化合物的结构。

  DOI：

  10.1016/s0040-4039(01)00068-5
• 作为产物：
  描述：

  2,3-二溴噻吩 、 三甲基氯硅烷 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以90%的产率得到3,5-dibromo-2-(trimethylsilyl)thiophene
  参考文献：
  名称：

  One-Pot Synthesis of Symmetric Octithiophenes from Asymmetric β-Alkylsulfanyl Bithiophenes

  摘要：

  Starting from 4-(octylsulfanyl)-2,2'-bithiophene, 4-bromo-4'-(octylsulfanyl)-2,2'-bithiophene, 4-iodo-4'-(octylsulfanyl)-2,2'-bithiophene, 4-bromo-4'-[(S)-2-methylbutylsulfanyl]-2,2'-bithiophene, and 4-iodo-4'-[(S)-2-methylbutylsulfanyl]-2,2'-bithiophene, a new series of symmetrically beta-substituted octithiophenes were synthesized by one-pot oxidative coupling with FeCl3. The octithiophenes obtained are soluble in common organic solvents and show different solvatochromic properties depending on the substitution type. In particular, the bromine atom exerts a positive influence on the supramolecular organization: the brominated octithiophenes display high filmability, solvatochromism, and CD induced by aggregation (when the chiral 2-methylbutylsulfanyl group is present), properties usually observed for polythiophenes. Density functional theory (DFT) calculations were carried out an a model bithiophene (4-substituted with a methylsulfanyl group) in order to understand the possible mechanism of the growth, the regiochemistry, and the reason for the polymerization leads to an octithiophene.

  DOI：

  10.1021/ma0614141

文献信息

• Antolini, Luciano; Goldoni, Francesca; Iarossi, Dario, Journal of the Chemical Society. Perkin transactions I, 1997, # 13, p. 1957 - 1961
  作者：Antolini, Luciano、Goldoni, Francesca、Iarossi, Dario、Mucci, Adele、Schenetti, Luisa

  DOI：——

  日期：——
• Base-catalyzed halogen dance reaction at thiophenes: a spectroscopic reinvestigation of the synthesis of 2,5-dibromo-3-(trimethylsilyl)thiophene
  作者：Hannes Froehlich、Wolfram Kalt

  DOI：10.1021/jo00297a003

  日期：1990.5
• One-Pot Synthesis of Symmetric Octithiophenes from Asymmetric β-Alkylsulfanyl Bithiophenes
  作者：Adele Mucci、Francesca Parenti、Rita Cagnoli、Rois Benassi、Alessio Passalacqua、Lisa Preti、Luisa Schenetti

  DOI：10.1021/ma0614141

  日期：2006.11.1

  Starting from 4-(octylsulfanyl)-2,2'-bithiophene, 4-bromo-4'-(octylsulfanyl)-2,2'-bithiophene, 4-iodo-4'-(octylsulfanyl)-2,2'-bithiophene, 4-bromo-4'-[(S)-2-methylbutylsulfanyl]-2,2'-bithiophene, and 4-iodo-4'-[(S)-2-methylbutylsulfanyl]-2,2'-bithiophene, a new series of symmetrically beta-substituted octithiophenes were synthesized by one-pot oxidative coupling with FeCl3. The octithiophenes obtained are soluble in common organic solvents and show different solvatochromic properties depending on the substitution type. In particular, the bromine atom exerts a positive influence on the supramolecular organization: the brominated octithiophenes display high filmability, solvatochromism, and CD induced by aggregation (when the chiral 2-methylbutylsulfanyl group is present), properties usually observed for polythiophenes. Density functional theory (DFT) calculations were carried out an a model bithiophene (4-substituted with a methylsulfanyl group) in order to understand the possible mechanism of the growth, the regiochemistry, and the reason for the polymerization leads to an octithiophene.
• Regiospecific silylation of 2,5-dibromothiophene: a reinvestigation
  作者：Edmunds Lukevics、Pavel Arsenyan、Sergey Belyakov、Juris Popelis、Olga Pudova

  DOI：10.1016/s0040-4039(01)00068-5

  日期：2001.3

  regiospecifically in accordance with the halogen dance mechanism to yield 3,5-dibromo-2-trimethylsilylthiophene or 3,4-dibromo-2,5-bis(trimethylsilyl)thiophene depending on the ratio of reagents. The outcome of the reaction was confirmed by further chemical transformations of the latter compound to 2,5-bis(trimethylsilyl)thiophene and 2,5-bis(trimethylsilyl)thiophene-1,1-dioxide. The structures of

  LDA将2,5-二溴噻吩与随后的甲硅烷基化反应按照卤素舞机理在区域上进行区域特异性反应，从而生成3,5-二溴-2-三甲基甲硅烷基噻吩或3,4-二溴-2,5-双（三甲基甲硅烷基）噻吩，具体取决于试剂的比例。该反应的结果通过后一种化合物进一步化学转化为2，5-双（三甲基甲硅烷基）噻吩和2，5-双（三甲基甲硅烷基）噻吩-1，1-二氧化物来证实。在砜的情况下，通过1 H，13 C和29 Si NMR以及X射线分析来确定所获得的化合物的结构。

表征谱图