Vinylsilane

Vinylsilane
Names
	Preferred IUPAC name Ethenylsilane
	Other names Vinyl silane
Identifiers
CAS Number	7291-09-0 ;
ECHA InfoCard	100.027.926
PubChem CID	81714;
UNII	J8E4H47LQC ;
CompTox Dashboard (EPA)	DTXSID10894876 ;
Properties
Chemical formula	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). Infobox references

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]

Substituted vinylsilanes

More 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]

Vinyltriethoxysilane is a common vinylsilane.

In the area of polymer chemistry and materials science, vinyltrimethoxysilane or vinyltriethoxysilane serve as monomers and coupling agents.

Preparation

Vinylsilanes 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

^ 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.

[1] 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.

[2] 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.

[3] 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.

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