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;
Beilstein Reference	1098318
ChEBI	CHEBI:27976;
ChEMBL	ChEMBL722;
ChemSpider	11721;
ECHA InfoCard	100.009.871
EC Number	210-857-4;
KEGG	C05985;
PubChem CID	12222;
UNII	SJ8A65XF7N ;
CompTox Dashboard (EPA)	DTXSID3060790 ;
	InChI InChI=1S/C3H2O/c1-2-3-4/h1,3H Key: IJNJLGFTSIAHEA-UHFFFAOYSA-N;
	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)
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H226, H300, H315, H317, H318, H319, H330, H335
Precautionary statements	P210, P233, P240, P241, P242, P243, P260, P264, P264+P265, P270, P271, P272, P280, P284, P301+P316, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P319, P320, P321, P330, P333+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, P501
	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.

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. Its explosive properties are attributed to the exothermicity of its polymerization.

Preparation

Its acetal can be prepared from acrolein.

Occurrence in interstellar medium

Propynal has been observed in the interstellar medium. It is hypothesized to be formed from a carbon monoxide-acetylene complex. Another possible pathway is through the reaction of propynylidyne (C₃H) with water.

Hazards

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

References

1 2 3 4 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 Dehydrohalogenation: 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] 1 2 3 4 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 Dehydrohalogenation: 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