Propargyl alcohol

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.[3] Propargyl alcohol is a colorless viscous liquid that is miscible with water and most polar organic solvents.

Propargyl alcohol
Names
IUPAC name
Prop-2-yn-1-ol
Other names
propynol, 2-propynol, 2-propyn-1-ol, prop-2-yn-1-ol, hydroxymethylacetylene.
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.003.157
KEGG
UNII
Properties
C3H4O
Molar mass 56.064 g·mol−1
Appearance Colorless to straw-colored liquid[1]
Odor geranium-like[1]
Density 0.9715 g/cm3
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)
miscible[1]
Vapor pressure 12 mmHg (20 °C)[1]
Hazards
Safety data sheet External SDS
GHS pictograms [2]
GHS Signal word Danger
GHS hazard statements
 H226, H301, H310, H330, H314, H373, H411[2]
NFPA 704 (fire diamond)
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineHealth code 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasReactivity code 3: Capable of detonation or explosive decomposition but requires a strong initiating source, must be heated under confinement before initiation, reacts explosively with water, or will detonate if severely shocked. E.g. hydrogen peroxideSpecial hazards (white): no code
3
3
3
Flash point 36 °C; 97 °F; 309 K (open cup)[1]
Lethal dose or concentration (LD, LC):
50 mg/kg (oral, rat)
NIOSH (US health exposure limits):
PEL (Permissible)
 none[1]
REL (Recommended)
 TWA 1 ppm (2 mg/m3) [skin][1]
IDLH (Immediate danger)
 N.D.[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

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[4] or propargylic acid.

Preparation

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.[5] It can also be prepared by dehydrochlorination of 3-chloro-2-propen-1-ol by NaOH.[6]

Safety

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

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See also

References
  1. NIOSH Pocket Guide to Chemical Hazards. "#0527". National Institute for Occupational Safety and Health (NIOSH).
  2. Record of Prop-2-yn-1-ol in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 11 March 2020.
  3. Merck Index, 11th Edition, 7819
  4. J. C. Sauer (1956). "Propionaldehyde". Organic Syntheses. 36: 66.; Collective Volume, 4, p. 813
  5. Falbe, Jürgen; Bahrmann, Helmut; Lipps, Wolfgang; Mayer, Dieter. "Alcohols, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_279..
  6. J. Am. Chem. Soc., 1944, 66 (2), pp 285–287
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