Trimethylsilylacetylene

Trimethylsilylacetylene
Names
	Preferred IUPAC name Ethynyltri(methyl)silane
Identifiers
CAS Number	1066-54-2 ;
3D model (JSmol)	Interactive image;
Abbreviations	TMSA
ChemSpider	59499 ;
ECHA InfoCard	100.012.655
EC Number	213-919-9;
PubChem CID	66111;
CompTox Dashboard (EPA)	DTXSID7061435 ;
	InChI InChI=1S/C5H10Si/c1-5-6(2,3)4/h1H,2-4H3 Key: CWMFRHBXRUITQE-UHFFFAOYSA-N ; 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
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H315, H318, H319, H335
Precautionary statements	P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, P501
Safety data sheet (SDS)	External MSDS
	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 a colorless liquid that is a derivative of acetylene.

Use

Called "tms acetylene", trimethylsilylacetylene is used as a source of "HC₂⁻". The trimethylsilyl group can then be cleaved off 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 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]

Trimethylsilylacetylene is a precursor to 1,4-bis(trimethylsilyl)buta-1,3-diyne, a protected form of 1,3-butadiyne.^[3]

History

Trimethylsilylacetylene was first synthesized in 1959 by Heinz Günter Viehe. He reduced chloro(trimethylsilyl)acetylene by reaction with phenyllithium in diethyl ether and proceeded with subsequent hydrolysis.^[4]

References

^ "Trimethylsilylacetylene". EROS. 2007. doi:10.1002/047084289X.rt288.pub2. ISBN 978-0471936237. {{cite encyclopedia}}: Cite uses deprecated parameter |authors= (help)
^ Andrew B. Holmes and Chris N. Sporikou (1993). "Trimethylsilylacetylene". Organic Syntheses; Collected Volumes, vol. 8, p. 606.
^ Graham E. Jones, David A. Kendrick, and Andrew B. Holmes (1987). "1,4-Bis(trimethylsilyl)buta-1,3-diyne". Organic Syntheses. 65: 52. doi:10.15227/orgsyn.065.0052.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ H. G. Viehe (1959), "Heterosubstituierte Acetylene, III. Nucleophile Substitutionen und Halogen-Metall-Austauschreaktionen an Dreifachbindungen", Chemische Berichte (in German), vol. 92, no. 12, pp. 3064–3075, doi:10.1002/cber.19590921209

[1] "Trimethylsilylacetylene". EROS. 2007. doi:10.1002/047084289X.rt288.pub2. ISBN 978-0471936237. {{cite encyclopedia}}: Cite uses deprecated parameter |authors= (help)

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

[3] Graham E. Jones, David A. Kendrick, and Andrew B. Holmes (1987). "1,4-Bis(trimethylsilyl)buta-1,3-diyne". Organic Syntheses. 65: 52. doi:10.15227/orgsyn.065.0052.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[viehe1959heterosubstituierte-4] H. G. Viehe (1959), "Heterosubstituierte Acetylene, III. Nucleophile Substitutionen und Halogen-Metall-Austauschreaktionen an Dreifachbindungen", Chemische Berichte (in German), vol. 92, no. 12, pp. 3064–3075, doi:10.1002/cber.19590921209

[1]

[2]

[3]

[4]