(5-氯-2-噻吩基)(三甲基)硅烷 | 23395-56-4

• 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: (5-氯-2-噻吩基)(三甲基)硅烷
• 英文名称: 2-chloro-5-trimethylsilylthiophene
• 英文别名: 5-chloro-2-trimethylsilylthiophene；(5-chloro-thiophen-2-yl)-trimethyl-silane；2-Chlor-5-trimethylsilyl-thiophen；2-Trimethylsilyl-5-chlorthiophen；5-Trimethylsilyl-2-chlorthiophen；2-(Trimethylsilyl)-5-chlorothiophene；(5-chlorothiophen-2-yl)-trimethylsilane
• CAS: 23395-56-4
• 化学式: C₇H₁₁ClSSi
• 分子量: 190.769
• InChiKey: COVFWQJNVZTDRL-UHFFFAOYSA-N

物化性质

• 沸点：
  205.1±20.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.95
• 重原子数：
  10
• 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

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  (5-氯-2-噻吩基)(三甲基)硅烷 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 2-氯噻吩
  参考文献：
  名称：

  取代的2-噻吩基三甲基硅烷的碱解速率。从头开始计算单取代噻吩的酸度

  摘要：

  Rates of cleavage in NaOMe-MeOH at 50°C have been determined for the mono-substituted 2-trimethylsilylthiophens X·C4H2S·SiMe3-2 with X = H, 3-NO2, 3-Br, 4-Br-, and 5-NO2, -CN, -COPh, -Me, -OMe and -NMe2, and for one disubstituted compound, 4,5-Br2-C4HS-SiMe3-2. For several compounds the rate and product isotope effects have also been determined. The energies involved in the process X·C4H3S → X·C4H2S−

  DOI：

  10.1016/s0022-328x(00)84581-7
• 作为产物：
  描述：

  2-氯噻吩 、 三甲基氯硅烷 在 sodium 作用下， 生成 (5-氯-2-噻吩基)(三甲基)硅烷
  参考文献：
  名称：

  取代的2-噻吩基三甲基硅烷的碱解速率。从头开始计算单取代噻吩的酸度

  摘要：

  Rates of cleavage in NaOMe-MeOH at 50°C have been determined for the mono-substituted 2-trimethylsilylthiophens X·C4H2S·SiMe3-2 with X = H, 3-NO2, 3-Br, 4-Br-, and 5-NO2, -CN, -COPh, -Me, -OMe and -NMe2, and for one disubstituted compound, 4,5-Br2-C4HS-SiMe3-2. For several compounds the rate and product isotope effects have also been determined. The energies involved in the process X·C4H3S → X·C4H2S−

  DOI：

  10.1016/s0022-328x(00)84581-7

文献信息

• Iridium-catalyzed borylation of thiophenes: versatile, synthetic elaboration founded on selective C–H functionalization
  作者：Ghayoor A. Chotana、Venkata A. Kallepalli、Robert E. Maleczka、Milton R. Smith

  DOI：10.1016/j.tet.2008.02.111

  日期：2008.6

  various substituted thiophenes to synthesize poly-functionalized thiophenes in good to excellent yields. Apart from common functionalities compatible with iridium-catalyzed borylations, additional functional group tolerance to acyl (COMe), and trimethylsilyl (TMS) groups was also observed. High regioselectivities were observed in borylation of 3-and 2,5-di-substituted thiophenes. Electrophilic aromatic

  铱催化的硼酸化反应已应用于各种取代的噻吩以合成多官能化的噻吩，收率非常好。除了与铱催化的硼化反应兼容的常见官能团外，还观察到了对酰基 (COMe) 和三甲基甲硅烷基 (TMS) 基团的额外官能团耐受性。在 3-和 2,5-二取代噻吩的硼酸化中观察到高区域选择性。噻吩硼酸酯上的亲电芳族 CH/C-Si 溴化显示在不破坏 CB 键的情况下发生，并且一锅 CH 硼酸化/Suzuki-Miyaura 交叉偶联已在 2-和 3-硼酸化噻吩上完成。
• The rates of base cleavage of substituted 2-thienyltrimethylsilanes. AB initio calculations of the acidities of monosubstituted thiophens
  作者：Giancarlo Seconi、Colin Eaborn、John G. Stamper

  DOI：10.1016/s0022-328x(00)84581-7

  日期：1981.1

  NaOMe-MeOH at 50°C have been determined for the mono-substituted 2-trimethylsilylthiophens X·C4H2S·SiMe3-2 with X = H, 3-NO2, 3-Br, 4-Br-, and 5-NO2, -CN, -COPh, -Me, -OMe and -NMe2, and for one disubstituted compound, 4,5-Br2-C4HS-SiMe3-2. For several compounds the rate and product isotope effects have also been determined. The energies involved in the process X·C4H3S → X·C4H2S− for deprotonation at

  Rates of cleavage in NaOMe-MeOH at 50°C have been determined for the mono-substituted 2-trimethylsilylthiophens X·C4H2S·SiMe3-2 with X = H, 3-NO2, 3-Br, 4-Br-, and 5-NO2, -CN, -COPh, -Me, -OMe and -NMe2, and for one disubstituted compound, 4,5-Br2-C4HS-SiMe3-2. For several compounds the rate and product isotope effects have also been determined. The energies involved in the process X·C4H3S → X·C4H2S−
• Kamigata, Nobumasa; Suzuki, Takashi; Yoshida, Masato, Phosphorus, Sulfur and Silicon and the Related Elements, 1990, vol. 53, # 1-4, p. 29 - 35
  作者：Kamigata, Nobumasa、Suzuki, Takashi、Yoshida, Masato

  DOI：——

  日期：——
• Gas-phase reactions of tetrachlorogermane with chlorothiophenes in the presence of hexachlorodisilane. Synthesis of thienylchlorogermanes
  作者：E. A. Chernyshev、N. G. Komalenkova、G. N. Yakovleva、V. G. Bykovchenko、M. A. Dubikhina、V. G. Lakhtin

  DOI：10.1134/s1070363207080051

  日期：2007.8

  Gas-phase reactions of dichlorogermylenes formed in the GeCl4-Si2Cl6 system with 2-chlorothiophene, 2,5-dichlorothiophene, 2,5-dichloro-3-methylthiophene, and 5-chloro-2-trimethylsilylthiophene is studied. It is shown that :GeCl2 is inserted into the chlorothiophene C-Cl bond to form the derivatives containing one or two trichlorogermyl groups. In the reaction with 5-chloro-2-trimethylsilylthiophene, the insertion of :GeCl2 into the C-Cl bond yielding 5-trichlorogermyl-2-trimethylsilylthiophene is accompanied by the exchange of the Me3Si group with the trichlorogermyl group to form 2,5-bis(trichlorogermyl)thiophene. The reactions occurring in the course of the synthesis of thienylchlorogermanes are considered.
• KAMIGATA, N.;SUZUKI, T.;YOSHIDA, M., PHOSPH. SULFUR AND SILICON AND RELAT. ELEM., 53,(1990) N-4, C. 29-35
  作者：KAMIGATA, N.、SUZUKI, T.、YOSHIDA, M.

  DOI：——

  日期：——