Propargyl alcohol
Names | |
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IUPAC name
2-Propyn-1-ol | |
Identifiers | |
107-19-7 | |
3D model (Jmol) | Interactive image |
ChEBI | CHEBI:28905 |
ChemSpider | 21106466 |
ECHA InfoCard | 100.003.157 |
KEGG | C05986 |
UNII | E920VF499L |
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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 | |
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). | |
verify (what is ?) | |
Infobox references | |
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 2 3 4 5 6 7 8 "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". Org. Synth. 36: 66.; Coll. Vol., 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