propiolaldehyde
{{Chembox
| ImageFile = Propinal.svg
| ImageSize = 200
| PIN = Prop-2-ynal
| OtherNames = Propynal; Propiolic aldehyde
| Section1 = {{Chembox Identifiers
| CASNo = 624-67-9
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII = SJ8A65XF7N
| UNII_Ref = {{fdacite|correct|FDA}}
| PubChem = 12222
| ChemSpiderID = 11721
| SMILES = C#CC=O
| StdInChI=
| StdInChIKey =
}}
| Section2 = {{Chembox Properties
| C=3|H=2|O=1
| Appearance = colorless liquid
| Density = 0.9152 g/cm3
| MeltingPtC =
| BoilingPtC = 54-57
| Solubility =
}}
| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
}}
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.{{cite encyclopedia |surname1=P. Perlmutter |chapter=Propargyl Aldehyde |date=2001 |doi=10.1002/047084289X.rp262m |title=Encyclopedia of Reagents for Organic Synthesis |isbn=978-0471936237}}
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
Occurrence in interstellar medium
Propynal has been observed in the interstellar medium. It is hypothesized to be formed from a carbon monoxide-acetylene complex.{{citation |last=Zhou |first=Li |author2=Ralf I. Kaiser |title=Pathways to Oxygen-Bearing Molecules in the Interstellar Medium and in Planetary Atmospheres: Cyclopropenone (c-C3H2O) and Propynal (HCCCHO) |journal=The Astrophysical Journal |year=2008 |volume=686 |issue=2 |pages=1493–1502 |doi=10.1086/591072 |doi-access=free }} Another possible pathway is through the reaction of propynylidyne (C3H) with water.{{citation |last=Xie |first=Hong-bin |author2=Chang-bin Shao |title=Radical-Molecule Reaction C3H + H2O on Amorphous Water Ice: A Promising Route for Interstellar Propynal |journal=The Astrophysical Journal |year=2007 |volume=670 |issue=1 |pages=449–456 |doi=10.1086/520757 |doi-access=free }}
Hazards
The compound is explosive, possibly because it tends to polymerize.
See also
References
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{{Molecules detected in outer space}}
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