|Jmol-3D images||Image 1|
|Molar mass||56.06 g mol−1|
-51--48 °C, 222-225 K, -60--54 °F
114-115 °C, 387-388 K, 237-239 °F
| (what is: / ?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Propargyl alcohol, or 2-propyn-1-ol, is an organic compound with the formula HC2CH2OH. It is the simplest stable alcohol containing an alkyne functional group. Propargyl alcohol is a colorless viscous liquid that is miscible with water and most polar organic solvents.
Reactions and applications
Propargyl alcohol polymerizes with heating or treatment with base. It is used as a corrosion inhibitor, a metal complex solution, a solvent stabilizer and an electroplating brightener additive. It is also used as an intermediate in organic synthesis. Propargyl alcohol tautomerizes to an enone (α,β-unsaturated ketone). An enal is an α,β-unsaturated aldehyde. Oxidation gives propionaldehyde.
Propargyl alcohol is produced by the copper-catalysed addition of formaldehyde to acetylene as a by-product of the industrial synthesis of but-2-yne-1,4-diol. It can also be prepared by dehydrochlorination of 3-chloro-2-propen-1-ol by NaOH.
Propargyl alcohol is a flammable liquid, toxic by inhalation, highly toxic by ingestion, toxic by skin absorption, and corrosive.
- Merck Index, 11th Edition, 7819
- J. C. Sauer (1956), "Propionaldehyde", Org. Synth. 36: 66; Coll. Vol. 4: 813
- Falbe, Jürgen; Bahrmann, Helmut; Lipps, Wolfgang; Mayer, Dieter (2005), "Alcohols, Aliphatic", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a01_279.
-  J. Am. Chem. Soc., 1944, 66 (2), pp 285–287