Trimethylsilylacetylene
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IUPAC name
ethynyltrimethylsilane
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3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.012.655 |
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PubChem CID
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| 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 |
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EU classification (DSD) (outdated)
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 F |
| R-phrases (outdated) | R11 |
| S-phrases (outdated) | S16 S24/25 S29 S33 S9 |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 (what is   ?) |
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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.
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