Propargyl alcohol

Propargyl alcohol
Names
IUPAC name
2-Propyn-1-ol
Identifiers
107-19-7 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:28905 YesY
ChemSpider 21106466 YesY
ECHA InfoCard 100.003.157
KEGG C05986 YesY
UNII E920VF499L 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 SDS
NFPA 704
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., gasoline) Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
3
3
0
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]
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).
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Infobox references
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.[2] 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[3] 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.[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. 1 2 3 4 5 6 7 8 "NIOSH Pocket Guide to Chemical Hazards #0527". National Institute for Occupational Safety and Health (NIOSH).
  2. ↑ Merck Index, 11th Edition, 7819
  3. ↑ J. C. Sauer (1956). "Propionaldehyde". Org. Synth. 36: 66.; Coll. Vol., 4, p. 813
  4. ↑ 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.
  5. ↑ J. Am. Chem. Soc., 1944, 66 (2), pp 285–287
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