ethenyltrimethylsilane

• ChemBase编号: 137326
• 分子式: C5H12Si
• 平均质量: 100.23428
• 单一同位素质量: 100.07082692
• SMILES: C[Si](C)(C)C=C
• Canonical SMILES: C=C[Si](C)(C)C
• InChI: InChI=1S/C5H12Si/c1-5-6(2,3)4/h5H,1H2,2-4H3
• InChIKey: GCSJLQSCSDMKTP-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: ethenyltrimethylsilane
• IUPAC传统名: silane, ethenyltrimethyl-
• 别名: 三甲基乙烯基硅烷; 三甲基硅乙烯; 乙烯基三甲基硅; 乙烯基三甲基硅烷; 三甲基乙烯基硅烷; (Trimethylsilyl)ethylene; Ethenyltrimethylsilane; Trimethyl(vinyl)silane; Vinyltrimethylsilane; Trimethyl(vinyl)silane; Trimethylvinylsilane; ethenyltrimethylsilane

登记号

• CAS号: 754-05-2
• EC号: 212-042-9
• MDL号: MFCD00008606
• Beilstein号: 956572
• PubChem SID: 24852813; 24884541; 162231589
• PubChem CID: 79102

理论计算性质

• 质子受体: 0
• 质子供体: 0
• LogD (pH = 5.5): 2.5601
• LogD (pH = 7.4): 2.5601
• Log P: 2.5601
• 摩尔折射率: 26.1296 cm^3
• 极化性: 12.652486 Å^3
• 极化表面积: 0.0 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

分子性质

理化性质

• 熔点: -132°C
• 沸点: 54-56°C; 55 °C(lit.)
• 闪点: -11.2 °F; -24 °C; -24°C(-11°F)
• 密度: 0.684 g/mL at 25 °C(lit.); 0.690
• 折射率: 1.3910; n20/D 1.391; n20/D 1.391(lit.)
• 蒸汽压: 4.44 psi ( 20 °C)
• 疏水性(logP): 2.809

安全信息

• 欧盟危险性物质标志: 易燃性(Flammable) (F); 刺激性(Irritant) (Xi); 有害性(Harmful) (Xn)
• 联合国危险货物编号: 1993; UN1993
• 德国WGK号: 3
• 联合国危险货物等级: 3
• 联合国危险货物包装类别(PG): 2; II
• 危险公开号: 11-22-36/37/38; 11-36/37/38
• 安全公开号: 16-26; 9-16-26-29-33-37
• TSCA收录: 是
• GHS危险品标识: GHS02; GHS07
• GHS警示词: Danger
• GHS危险声明: H225-H302-H315-H319-H335; H225-H315-H319-H335
• GHS警示性声明: P210-P261-P305 + P351 + P338; P210-P280G-P243-P305+P351+P338-P403+P233
• 个人保护装置: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US)
• RID/ADR: UN 1993 3/PG 2

产品相关信息

• 纯度: ≥97.0% (GC); ≥99.5%; 95%; 97%; 98+%
• 级别: purum
• 杂质: <3% tetrahydrofuran
• 线性分子式: (CH3)3SiCHCH2

详细说明

Sigma Aldrich - 213950

Application
用于制备三甲基硅基乙基亚砜，该化合物在氟离子存在下可以生成次磺酸盐亲核试剂。1
包装
5, 25, 100 g in glass bottle

Sigma Aldrich - 661724

Application
铑(I) 催化下制备甲硅烷基醚。1
包装
25 g in glass bottle

Sigma Aldrich - 95100

Other Notes
综述1,2,3,4

参考文献

• Useful ethylene equivalent in its reaction with electrophiles. The reactivity is controlled by the ability of the Si atom to stabilize a positive charge on a ?-carbon atom. See Appendix 4.
• Acylation under Friedel-Crafts conditions leads to vinyl ketones. Using ɑ?-unsaturated acyl halides, the products are divinyl ketones, which, under the reaction conditions, undergo the Nazarov cyclization to enones: J. Org. Chem., 45, 1046 (1980):
  
• For reviews of the Nazarov cyclization, see: Synthesis, 429 (1983); Org. React., 45, 159 (1994).
• Coupling with the electrophilic reagent generated from an aryl iodide in the presence of Pd(OAc)₂, triphenylphosphine and base, provides a route to styrenes: Chem. Lett., 1993 (1982).
• Also undergoes regioselective addition reactions with alkyllithiums: J. Chem. Soc., Perkin 1, 1131 (1983), and Grignards: Chem. Ber., 117, 383 (1984), to giveɑ-metallated products.
• For use in a 2-carbon extension of aldehydes to ɑ?-unsaturated aldehydes based on cycloaddition to the nitrone, see N-Methylhydroxylamine hydrochloride, L02202.
• For an extensive review of the reactions of vinyl (and allyl) silanes, see: Org. React., 37, 57 (1989).