Trimethylsilylacetylene

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Trimethylsilylacetylene
Trimethylsilylacetylene.PNG
Names
IUPAC name
ethynyltrimethylsilane
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.012.655
Properties
C5H10Si
Molar mass 98.22 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
Highly Flammable 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R-phrases (outdated) R11
S-phrases (outdated) S16 S24/25 S29 S33 S9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).
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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[edit]

  1. ^ Andrew B. Holmes and Chris N. Sporikou (1993). "Trimethylsilylacetylene". Org. Synth. ; Coll. Vol., 8, p. 606