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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.012.655
Properties
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
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R-phrases (outdated) R11
S-phrases (outdated) S16 S24/25 S29 S33 S9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. ISBN 978-0471936237.CS1 maint: uses authors parameter (link)
  2. Andrew B. Holmes and Chris N. Sporikou (1993). "Trimethylsilylacetylene". Organic Syntheses.; Collective Volume, 8, p. 606
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