Propiolaldehyde Explained

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. Another possible pathway is through the reaction of propynylidyne (C₃H) with water.

Hazards

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

See also

• Acrolein
• Propiolic acid

Notes and References

1. Encyclopedia: P. Perlmutter . Propargyl Aldehyde . 2001 . 10.1002/047084289X.rp262m . Encyclopedia of Reagents for Organic Synthesis . 978-0471936237.
2. 10.15227/orgsyn.059.0010. Alkyness via Phase Transfer-Catalyzed Dehydrohalogenatiion: Propiolaldehyde Diethyl Acetal. Organic Syntheses. 1979. 59. 10. A. Le Coq and A. Gorgues.