Propargyl alcohol

Propargyl alcohol

Propargyl alcohol
Names
IUPAC name
2-Propyn-1-ol
Identifiers
 YesY
ChEBI  YesY
ChemSpider  YesY
Jmol-3D images Image
KEGG  YesY
Properties
C3H4O
Molar mass 56.06 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 MSDS
NFPA 704
3
4
3
Flash point 36 °C; 97 °F; 309 K (open cup)[1]
US health exposure limits (NIOSH):
PEL (Permissible)
none[1]
REL (Recommended)
TWA 1 ppm (2 mg/m3) [skin][1]
N.D.[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 YesY  (: YesY/N?)

Propargyl alcohol, or 2-propyn-1-ol, is an formula C3H4O. It is the simplest stable alcohol containing an alkyne functional group.[2] Propargyl alcohol is a colorless viscous liquid that is miscible with water and most polar organic solvents.

Reactions and applications

Propargyl alcohol enone (α,β-unsaturated ketone). Oxidation gives propionaldehyde.[3]

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

Safety

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

See also

References

  1. ^ a b c d e f g h
  2. ^ Merck Index, 11th Edition, 7819
  3. ^ ;
  4. ^ .
  5. ^ [1] J. Am. Chem. Soc., 1944, 66 (2), pp 285–287

External links

  • Hazardous substance fact sheet for propargyl alcohol
  • CDC - NIOSH Pocket Guide to Chemical Hazards