Allyltrichlorosilane

Allyltrichlorosilane
Names
	Preferred IUPAC name Trichloro(prop-2-enyl)silane
Identifiers
CAS Number	107-37-9;
3D model (JSmol)	Interactive image;
ChemSpider	13862317;
ECHA InfoCard	100.003.170
EC Number	203-485-9;
PubChem CID	7867;
UNII	UB3N98803N;
UN number	1724
CompTox Dashboard (EPA)	DTXSID3059347 ;
	InChI InChI=1S/C3H5Cl3Si/c1-2-3-7(4,5)6/h2H,1,3H2 Key: HKFSBKQQYCMCKO-UHFFFAOYSA-N;
	SMILES C=CC[Si](Cl)(Cl)Cl;
Properties
Chemical formula	C3H5Cl3Si
Molar mass	175.51 g·mol−1
Appearance	white solid
Density	1.2011 g/cm3
Melting point	35 °C (95 °F; 308 K)
Boiling point	117.5 °C (243.5 °F; 390.6 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H314
Precautionary statements	P210, P233, P240, P241, P242, P243, P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P370+P378, P403+P235, P405, P501
Flash point	35°C
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Allyltrichlorosilane is an organosilicon compound with the formula Cl₃SiCH₂CH=CH₂. It is a colorless or white low-melting solid.^[1] It was originally prepared by the Direct process, the reaction of allyl chloride with copper-silicon alloy.^[2]

The compound is bifunctional, containing reactive trichlorsilyl and allyl groups. The SiCl₃ group undergoes the usual alcoholysis to give the trialkxoyallylsilane. In the presence of Lewis bases, the reagent allylates aldehydes.

References

^ Kočovský, Pavel (2006). "Allyltrichlorosilane". E-EROS Encyclopedia of Reagents for Organic Synthesis: 1–4. doi:10.1002/047084289X. hdl:10261/236866. ISBN 9780470842898.
^ Hurd, Dallas T. "Preparation of vinyl and allyl chlorosilanes" Journal of the American Chemical Society 1945, volume 67, 1813-14. doi:10.1021/ja01226a058

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[1] Kočovský, Pavel (2006). "Allyltrichlorosilane". E-EROS Encyclopedia of Reagents for Organic Synthesis: 1–4. doi:10.1002/047084289X. hdl:10261/236866. ISBN 9780470842898.

[2] Hurd, Dallas T. "Preparation of vinyl and allyl chlorosilanes" Journal of the American Chemical Society 1945, volume 67, 1813-14. doi:10.1021/ja01226a058

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