Vinylsilane refers to an organosilicon compound with chemical formula CH2=CHSiH3. It is a derivative of silane (SiH4). The compound, which is a colorless gas, is mainly of theoretical interest.[1]
| |
| Names | |
|---|---|
| Preferred IUPAC name
Ethenylsilane | |
| Other names
Vinyl silane
| |
| Identifiers | |
| ECHA InfoCard | 100.027.926 |
PubChem CID
|
|
| UNII | |
CompTox Dashboard (EPA)
|
|
| Properties | |
| C2H6Si | |
| Molar mass | 58.155 g·mol−1 |
| Appearance | colorless gas |
| Boiling point | −22.8 °C (−9.0 °F; 250.3 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
Substituted vinylsilanes
editMore commonly used than the parent vinylsilane are vinyl-substituted silanes with other substituents on silicon. In the area of organic synthesis, vinylsilanes are useful intermediates.[2]
In the area of polymer chemistry and materials science, vinyltrimethoxysilane or vinyltriethoxysilane serve as monomers and coupling agents.
Preparation
editVinylsilanes are often prepared by hydrosilylation of alkynes. They can be made by the reaction of alkenyl lithium and Grignard reagents with chlorosilanes. In some cases dehydrogenative silylation is another method.[3]
References
edit- ^ Ring, M. A.; O'Neal, H. E.; Rickborn, S. F.; Sawrey, B. A. (1983). "Kinetics of the high-temperature thermal decomposition of silanes and alkylsilanes". Organometallics. 2 (12): 1891–4. doi:10.1021/om50006a038.
- ^ Fleming, Ian; Dunogues, Jacques; Smithers, Roger (1989). "The electrophilic substitution of allylsilanes and vinylsilanes". Organic Reactions. 37: 57–575. doi:10.1002/0471264180.or037.02. ISBN 0471264180.
- ^ Lu, B.; Falck, J. R. (2010). "Iridium-Catalyzed (Z)-Trialkylsilylation of Terminal Olefins". J. Org. Chem. 75 (5): 1701–1705. doi:10.1021/jo902678p. PMC 2830331. PMID 20136153.