Cyclopropenone

Cyclopropenone is an organic compound with molecular formula C₃H₂O consisting of a cyclopropene carbon framework with a ketone functional group. It is a colorless, volatile liquid that boils near room temperature.^[1] Neat cyclopropenone polymerizes upon standing at room temperature,^[2] and chemical vendors typically supply it as an acetal.^[3] The chemical properties of the compound are dominated by the strong polarization of the carbonyl group, which gives a partial positive charge with aromatic stabilization on the ring and a partial negative charge on oxygen.^[4][5] Cyclopropenone has been observed in the gas phase in interstellar environments such as the Taurus Molecular Cloud.^[6]

Cyclopropenone

Main resonance structures of cyclopropenone.
Names
Preferred IUPAC name Cycloprop-2-en-1-one
Other names Cyclopropenone, Cyclopropene-3-one
Identifiers
CAS Number	2961-80-0 Y
3D model (JSmol)	Interactive image
ChemSpider	121433
PubChem CID	137779
UNII	5MPZ6QZ6ZF Y
CompTox Dashboard (EPA)	DTXSID50183796
InChI InChI=1S/C3H2O/c4-3-1-2-3/h1-2H Key: GGRQLKPIJPFWEZ-UHFFFAOYSA-N InChI=1/C3H2O/c4-3-1-2-3/h1-2H Key: GGRQLKPIJPFWEZ-UHFFFAOYAI
SMILES c1cc1=O
Properties
Chemical formula	C3H2O
Molar mass	54.048 g·mol−1
Appearance	Colorless liquid
Melting point	−29 to −28 °C (−20 to −18 °F; 244 to 245 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

See also

• Diphenylcyclopropenone
• Deltic acid
• Tropone