Propynal

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Propynal
Propynal-2D-skeletal.png
Names
Other names
Propiolaldehyde, propiolic aldehyde
Identifiers
  • 624-67-9
3D model (JSmol)
  • Interactive image
ChemSpider
  • 11721
ECHA InfoCard 100.009.871
PubChem CID
  • 12222
Properties
C3H2O
Molar mass 54.05 g·mol−1
Melting point 59–61 °C (138–142 °F; 332–334 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Propynal 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]

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]

Occurrence in interstellar medium

Propynal has been observed in the interstellar medium. It is hypothesized to be formed from a carbon monoxide-acetylene complex.[2] Another possible pathway is through the reaction of propynylidyne (C3H) with water.[3]

Hazards

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

See also

References

  1. ^ a b c P. Perlmutter (2001), "Propargyl Aldehyde", e-EROS Encyclopedia of Reagents for Organic Synthesis, doi:10.1002/047084289X.rp262m 
  2. ^ 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/meta 
  3. ^ 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), doi:10.1086/520757/meta 


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