(2-thienyl)vinyldichlorosilane | 78819-22-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2-thienyl)vinyldichlorosilane
• 英文别名: Vinyl(2-thienyl)dichlorosilane；dichloro-ethenyl-thiophen-2-ylsilane
• CAS: 78819-22-4
• 化学式: C₆H₆Cl₂SSi
• 分子量: 209.171
• InChiKey: UGFDJIXLQUMXLQ-UHFFFAOYSA-N

物化性质

• 沸点：
  221.0±22.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• 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：

  甲基碘化镁 、 (2-thienyl)vinyldichlorosilane 以 乙醚 为溶剂， 反应 1.0h， 以33%的产率得到2-(vinyldimethylsilyl)thiophene
  参考文献：
  名称：

  Synthesis of Thiophene Derivatives Bearing a Silicon Atom

  摘要：

  Synthesis of thiophene derivatives containing a silicon atom is described. Silylation of 2-thienylmethyl chloride (12) with trichlorovinylsilane or chloro(chloromethyl)dimethylsilane was accomplished by addition of 12 to a mixture of Mg and the former reagent in THF or by addition of a mixture of 12 and the latter reagent to a mixture of Mg in THF to give dichloro(2-thienylmethyl)vinylsilane (13) or chloromethyl(dimethyl)(2-thienylmethyl) (18). The Grignard reagent (19) of 18 reacted with carbon dioxide, dimethyl carbonate or benzaldehyde to produce dimethyl(2-thienylmethyl)silylacetic acid (20), methyl dimethyl(2-thienylmethyl)silylacetate (21) or 2'-[dimethyl(2-thienylmethyl)silyl]-1'-phenylethanol (22).

  DOI：

  10.3987/com-96-s51
• 作为产物：
  描述：

  2-噻吩基锂 、 乙烯基三氯硅烷 以 四氢呋喃 为溶剂， 以58%的产率得到(2-thienyl)vinyldichlorosilane
  参考文献：
  名称：

  Chemical modification of poly(n-hexylsilane) – Synthesis of functional polysilanes bearing thienyl groups on the appended sila-alkyl side chains and their application in the generation and stabilization of silver nanoparticles

  摘要：

  The linear polysilanes [{RR'Si-2(CH2)(y)Si(n-hex)}(x){HSi(n-hex)}(1-x)](n) (1-4; R =2-thienyl, R' = H; R = Me, R' = 2-thienyl; y = 2, 3) have been synthesized by hydrosilylation reaction between preformed poly(n-hexylsilane) and (2-thienyl)vinyldichlorosilane/allyl(2-thienyl)dichlorosilane/bis(2-thienyl)methylvinylsilane/allyl-bis(2-thienyl)methylsilane using AIBN as the free radical initiator. GPC analysis reveals a monomodal molecular weight distribution in each case with M-w = 2492-3280 and PDI = 1.18-1.44. The polysilane 1 (R = 2-thienyl, R' = H, y = 2) acts as reducing agent towards silver tetrafluoroborate under mild conditions (cyclohexane, rt, 5 h) to afford spherical silver nanoparticles of size 8.4 +/- 0.7 nm, as evident from the TEM and dynamic light scattering (DLS) studies. The silver nanoparticles in the polymer matrix exhibit surface plasmon absorption at 420 nm suggesting the donor acceptor interaction between the thienyl group and the metal nanocluster surface. This stabilization effect provides long shelf life stability to the nanoparticles in solution with no sign of agglomeration even after three months. (C) 2007 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2007.10.052