Propiolaldehyde
| Names | |
|---|---|
| Preferred IUPAC name
Prop-2-ynal | |
| Other names
Propynal; Propiolic aldehyde
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.009.871 |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C3H2O | |
| Molar mass | 54.048 g·mol−1 |
| Appearance | colorless liquid |
| Density | 0.9152 g/cm3 |
| Boiling point | 54–57 °C (129–135 °F; 327–330 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Propiolaldehyde is an organic compound with molecular formula HC2CHO. It is the simplest chemical compound containing both alkyne and aldehyde functional groups. It is a colorless liquid with explosive properties.[1]
Reactions
[edit]The compound exhibits reactions expected for an electrophilic alkynyl aldehyde. It is a dienophile and a good Michael acceptor. Grignard reagents add to the carbonyl center.[1] Its explosive properties are attributed to the exothermicity of its polymerization.[1]
Preparation
[edit]Its acetal can be prepared from acrolein.[2]
Occurrence in interstellar medium
[edit]Propynal has been observed in the interstellar medium. It is hypothesized to be formed from a carbon monoxide-acetylene complex.[3] Another possible pathway is through the reaction of propynylidyne (C3H) with water.[4]
Hazards
[edit]The compound is explosive, possibly because it tends to polymerize.[1]
See also
[edit]References
[edit]- ^ a b c d P. Perlmutter (2001). "Propargyl Aldehyde". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rp262m. ISBN 978-0471936237.
- ^ A. Le Coq and A. Gorgues (1979). "Alkyness via Phase Transfer-Catalyzed Dehydrohalogenatiion: Propiolaldehyde Diethyl Acetal". Organic Syntheses. 59: 10. doi:10.15227/orgsyn.059.0010.
- ^ Zhou, Li; Ralf I. Kaiser (2008), "Pathways to Oxygen-Bearing Molecules in the Interstellar Medium and in Planetary Atmospheres: Cyclopropenone (c-C3H2O) and Propynal (HCCCHO)", The Astrophysical Journal, 686 (2): 1493–1502, doi:10.1086/591072
- ^ Xie, Hong-bin; Chang-bin Shao (2007), "Radical-Molecule Reaction C3H + H2O on Amorphous Water Ice: A Promising Route for Interstellar Propynal", The Astrophysical Journal, 670 (1): 449–456, doi:10.1086/520757