Trimethylsilylacetylene

Trimethylsilylacetylene is the acetylene HC₂Si(CH₃)₃. It is a colorless liquid. Called "tms acetylene", it is used as a source of "HC₂⁻". The trimethylsilyl group protected can be desilyated with TBAF. Using this protected alkyne, as opposed to acetylene itself, prevents further coupling reactions and also has the benefit of being a liquid.[1] A less expensive alternative reagent is 2-methylbut-3-yn-2-ol, which after alkynylation is deprotected with base.

Trimethylsilylacetylene

Names
IUPAC name ethynyltrimethylsilane
Identifiers
CAS Number	1066-54-2^Y
3D model (JSmol)	Interactive image
ChemSpider	59499^Y
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^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
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)
Hazards
Safety data sheet	External MSDS
EU classification (DSD) (outdated)	F
R-phrases (outdated)	R11
S-phrases (outdated)	S16 S24/25 S29 S33 S9
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is ^YN ?)
Infobox references

Trimethylsilylacetylene 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.[2]

References

1. Godson C. Nwokogu, Saskia Zemolka, Florian Dehme (2007). "Trimethylsilylacetylene". EROS. doi:10.1002/047084289X.rt288.pub2.CS1 maint: uses authors parameter (link)
2. Andrew B. Holmes and Chris N. Sporikou (1993). "Trimethylsilylacetylene". Organic Syntheses.; Collective Volume, 8, p. 606