Propiolaldehyde

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]

Propiolaldehyde
Names
Preferred IUPAC name
Prop-2-ynal
Other names
Propynal; Propiolic aldehyde
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.009.871
UNII
  • C#CC=O
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).
Infobox references

Reactions

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

Its acetal can be prepared from acrolein.[2]

Occurrence in interstellar medium

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

The compound is explosive, possibly because it tends to polymerize.[1]

See also

References
  1. P. Perlmutter (2001). "Propargyl Aldehyde". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rp262m. ISBN 978-0471936237.
  2. 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.
  3. 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), doi:10.1086/591072
  4. 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
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