Propargyl alcohol
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| Names | |
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| IUPAC name
2-Propyn-1-ol
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| Identifiers | |
107-19-7  |
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| ChEBI | CHEBI:28905 |
| ChemSpider | 21106466 |
| Jmol 3D model | Interactive image |
| KEGG | C05986 |
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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] |
| Vapor pressure | {{{value}}} |
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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, 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.
Contents
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
- ↑ 1.0 1.1 1.2 1.3 Cite error: Invalid
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- ↑ [1] J. Am. Chem. Soc., 1944, 66 (2), pp 285–287
