Propiolaldehyde

Propiolaldehyde
Names
	Preferred IUPAC name Prop-2-ynal
	Other names Propynal; Propiolic aldehyde
Identifiers
CAS Number	624-67-9 ;
3D model (JSmol)	Interactive image;
ChemSpider	11721;
ECHA InfoCard	100.009.871
PubChem CID	12222;
UNII	SJ8A65XF7N ;
CompTox Dashboard (EPA)	DTXSID3060790 ;
	SMILES C#CC=O;
Properties
Chemical formula	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

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

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]

References

^ ^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

[eros-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): 1493–1502, 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

[1]