Propargyl alcohol
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| UN number | 1986 2929 |
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| Appearance | Colorless to straw-colored liquid[1] |
| Odor | geranium-like[1] |
| Density | 0.9715 g/cm3 |
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| Vapor pressure | 12 mmHg (20 °C)[1] |
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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.
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).[4]
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.[5] It can also be prepared by dehydrochlorination of 3-chloro-2-propen-1-ol by NaOH.[6]
Safety
Propargyl alcohol is a flammable liquid, toxic by inhalation, highly toxic by ingestion, toxic by skin absorption, and corrosive.Script error: No such module "Unsubst".
See also
References
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- ↑ a b c d e f g h Script error: No such module "citation/CS1".
- ↑ Merck Index, 11th Edition, 7819
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- ↑ Script error: No such module "citation/CS1".
- ↑ Template:Ullmann.
- ↑ [1] J. Am. Chem. Soc., 1944, 66 (2), pp 285–287
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External links
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