3D model (JSmol)
|Molar mass||56.06 g·mol−1|
|Appearance||Colorless to straw-colored liquid|
|Melting point||−51 to −48 °C (−60 to −54 °F; 222 to 225 K)|
|Boiling point||114 to 115 °C (237 to 239 °F; 387 to 388 K)|
|Vapor pressure||12 mmHg (20 °C)|
|Safety data sheet||External SDS|
|Flash point||36 °C; 97 °F; 309 K (open cup)|
|US health exposure limits (NIOSH):|
|TWA 1 ppm (2 mg/m3) [skin]|
IDLH (Immediate danger)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
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.
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. 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.
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.
- "NIOSH Pocket Guide to Chemical Hazards #0527". National Institute for Occupational Safety and Health (NIOSH).
- Merck Index, 11th Edition, 7819
- J. C. Sauer (1956). "Propionaldehyde". Organic Syntheses. 36: 66.; Collective Volume, 4, p. 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