Trimethylsilylacetylene

Trimethylsilylacetylene

IUPAC name ethynyl-trimethyl-silane
Identifiers
CAS number	1066-54-2^Y
PubChem	66111
ChemSpider	59499^Y
Jmol-3D images	Image 1
SMILES C#C[Si](C)(C)C
InChI InChI=1S/C5H10Si/c1-5-6(2,3)4/h1H,2-4H3^Y Key: CWMFRHBXRUITQE-UHFFFAOYSA-N^Y InChI=1S/C5H10Si/c1-5-6(2,3)4/h1H,2-4H3 InChI=1S/C5H10Si/c1-5-6(2,3)4/h1H,2-4H3 Key: CWMFRHBXRUITQE-UHFFFAOYSA-N
Properties
Molecular formula	C₅H₁₀Si
Molar mass	98.22 g mol⁻¹
Appearance	colorless liquid
Density	0.69 g/mL
Boiling point	53 °C, 326 K, 127 °F
Hazards
MSDS	External MSDS
EU classification	F
R-phrases	R11
S-phrases	S16 S24/25 S29 S33 S9
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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 and also has the benefit of being a liquid.

This compound is commercially 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", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv8p0606 ; Coll. Vol. 8: 606