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
Preferred IUPAC name
Prop-2-yn-1-ol
Other names
propynol, 2-propynol, 2-propyn-1-ol, hydroxymethylacetylene.
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.157
EC Number
  • 203-471-2
KEGG
RTECS number
  • UK5075000
UNII
UN number 1986 2929
  • InChI=1S/C3H4O/c1-2-3-4/h1,4H,3H2 Y
    Key: TVDSBUOJIPERQY-UHFFFAOYSA-N Y
  • InChI=1/C3H4O/c1-2-3-4/h1,4H,3H2
    Key: TVDSBUOJIPERQY-UHFFFAOYAE
  • C#CCO
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[2]
GHS labelling:
Danger
H226, H301, H310, H314, H330, H373, H411
P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P273, P280, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P311, P312, P321, P322, P330, P361, P363, P370+P378, P391, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)
3
3
3
Flash point 36 °C; 97 °F; 309 K (open cup)[1]
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]
Safety data sheet (SDS) External SDS
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.

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).[5]

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.[6] It can also be prepared by dehydrochlorination of 3-chloro-2-propen-1-ol by NaOH.[7]

Safety

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

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, vol. 4, p. 813
  5. Anslyn, Eric V., 1960- (2006). Modern physical organic chemistry. Dougherty, Dennis A., 1952-. Mill Valley, California: University Science Books. ISBN 1-891389-31-9. OCLC 55600610.{{cite book}}: CS1 maint: multiple names: authors list (link)
  6. 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..
  7. J. Am. Chem. Soc., 1944, 66 (2), pp 285–287
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