Old phenylacetylene in a glass pipette
| IUPAC name
| Other names
|Molar mass||102.133 g/mol|
|Appearance||Colorless or yellow liquid|
|Density||0.9281 g/cm3 (25 °C)|
|Melting point||−44.8 °C (−48.6 °F; 228.3 K)|
|Boiling point||143 °C (289 °F; 416 K)|
|Solubility||Miscible with acetone, alcohols, benzene, chloroform, ethers, pyridine, toluene|
|Vapor pressure||17.6 mm Hg (37.7 °C)|
|Acidity (pKa)|| 23.2 (aq, extrapolated)|
|Safety data sheet||Sigma-Aldrich|
|Flash point||27 °C (80.6 °F; 300 K)|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Phenylacetylene is an alkyne hydrocarbon containing a phenyl group. It exists as a colorless, viscous liquid, though older samples are yellow in color, due to oxidation. In research, it is sometimes used as an analog for acetylene, as being a liquid, it is easier to handle than acetylene gas.
Phenylacetylene burns in air releasing lots of soot.
Phenylacetylene can be reduced by hydrogen over Lindlar catalyst to give styrene.
It undergoes a hydration reaction, catalyzed by gold(III) or mercury(II), to give acetophenone.
Phenylacetylene is a colorless liquid, that turns yellow over time if exposed to air.
Phenylacetylene is sold by chemical suppliers.
Ethanol can be used instead of glycerol.
- Substitute for acetylene in chemical reactions
- Synthesis of acetophenone
- Sonogashira coupling
- Synthesis of rubrene
Phenylacetylene is harmful and flammable. Wear proper protection when handling it.
In closed amber bottles, away from light and air. Inert gas, like argon can be used to limit oxidation.
Should be burned in an incinerator, best in a strong oxidizing atmosphere.
- Streitwieser, A.,Jr.; Ruben, D.M.E; J. Am. Chem. Soc. 1971., 93, p. 1794-1795
- Bordwell, F.G. Acc. Chem. Res. 1988, 21, p. 456-463