Trimethylsilylacetylene

Trimethylsilylacetylene
Names
	IUPAC name ethynyl-trimethyl-silane
Identifiers
CAS Number	1066-54-2 ;
3D model (JSmol)	Interactive image;
ChemSpider	59499;
ECHA InfoCard	100.012.655
PubChem CID	66111;
CompTox Dashboard (EPA)	DTXSID7061435 ;
	InChI InChI=1S/C5H10Si/c1-5-6(2,3)4/h1H,2-4H3;
	SMILES C#C[Si](C)(C)C;
Properties
Chemical formula	C5H10Si
Molar mass	98.220 g·mol−1
Appearance	colorless liquid
Density	0.69 g/mL
Boiling point	53 °C (127 °F; 326 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Trimethylsilylacetylene is an acetylene molecule protected on one end by the trimethylsilyl group. It is popularly used in alkynylations, e.g. the Sonogashira reaction. After desilylation (e.g. with TBAF), the ethynyl group is introduced. Using a protected alkyne, as opposed to acetylene gas, prevents further (undesired) coupling reactions.

This compound is comercially available. It may also be prepared in a manner similar to other silyl compounds: deprotonation of acetylene with a Grignard reagent, followed by reaction with trimethylsilyl chloride.^[1]

References

^ Andrew B. Holmes and Chris N. Sporikou (1993). "Trimethylsilylacetylene". Organic Syntheses; Collected Volumes, vol. 8, p. 606.

[1] Andrew B. Holmes and Chris N. Sporikou (1993). "Trimethylsilylacetylene". Organic Syntheses; Collected Volumes, vol. 8, p. 606.

[1]