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Propargyl alcohol

Chemical compound

Wikipedia contributorsAdapted for Fathomly · View authors
1 min read
Source updated August 13, 2025
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Propargyl alcohol, or 2-propyn-1-ol, is an organic compound with the formula C3H4O. 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.

01Reactions 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. Secondary and tertiary substituted propargylic alcohols undergo catalyzed rearrangement reactions to form α,β-unsaturated carbonyl compounds via the Meyer-Schuster rearrangement and others. It can be oxidized to propynal or propargylic acid.

As an indication of the electronegativity of an sp carbon, propargyl alcohol is significantly more acidic (pKa = 13.6) compared to its sp2-containing analog allyl alcohol (pKa = 15.5), which is in turn more acidic than the fully saturated (sp3 carbons only) n-propyl alcohol (pKa = 16.1).

02Preparation

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.

03Safety

Propargyl alcohol is a flammable liquid, toxic by inhalation, highly toxic by ingestion, toxic by skin absorption, and corrosive.

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Sources and credits

This article is adapted from the Wikipedia article “Propargyl alcohol”, written by its contributors and licensed under CC BY-SA 4.0. Fathomly has changed the layout, removed citation markers, navigation and maintenance notices, and adjusted punctuation. This adapted version is shared under the same license. For references, see the original article.

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Related topics

Alkynylation

In organic chemistry, alkynylation is an addition reaction in which a terminal alkyne is added to a carbonyl group (C=O) to form an propargylic alcohol (R2C(−OH)−C≡C−R'). When the acetylide is formed from acetylene (HC≡CH), the reaction gives an α-ethynyl alcohol.

Allyl alcohol

Allyl alcohol is an organic compound with the structural formula CH2=CHCH2OH. Like many alcohols, it is a water-soluble, colourless liquid. It is more toxic than typical small alcohols.

Propargyl group

In organic chemistry, the propargyl group is a functional group of 2-propynyl with the structure HC≡C−CH2−. It is an alkynyl group derived from propyne.