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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. Neat cyclopropenone polymerizes upon standing at room temperature, and chemical vendors typically supply it as an acetal. 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.Main resonance structures of cyclopropenone

Last revised
Jul 27, 2026
Read time
≈ 2 min
Length
349 w
Citations
6
Source
Wikipedia ↗
Cyclopropenone
source ↗
source ↗
Names
Preferred IUPAC name
Cycloprop-2-en-1-one
Other names
Cyclopropenone, Cyclopropene-3-one
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • 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
  • c1cc1=O
Properties
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).

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.45

Main resonance structures of cyclopropenone source ↗

Cyclopropenone has been observed in the gas phase in interstellar environments such as the Taurus molecular cloud.6

See also

See also

References

References

  1. "Cyclopropenone". Organic Syntheses. 57: 41. 1977. doi:10.15227/orgsyn.057.0041.
  2. Breslow, Ronald; Oda, Masaji (1972-06-01). "Isolation and characterization of pure cyclopropenone". Journal of the American Chemical Society. 94 (13): 4787–4788. Bibcode:1972JAChS..94.4787B. doi:10.1021/ja00768a089. ISSN 0002-7863.
  3. Elliott, Gregory I.; Boger, Dale L. (2004). "Cyclopropene, 3,3‑Dimethoxy". Cyclopropene, 3,3-Dimethoxy. Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rn00486. ISBN 0-471-93623-5. Dimethyl cyclopropenone ketal is less stable than the corresponding cyclic ketal derivatives....A direct route to cyclopropenone is the hydrolysis of 3,3‑dimethoxy­cyclopropene.
  4. "Experiments show cyclopropenone is aromatic". Chem. Eng. News. 61 (38): 33. 1983. doi:10.1021/cen-v061n038.p033.
  5. Peart, Patricia A.; Tovar, John D. (2010). "Poly(cyclopropenone)s: Formal Inclusion of the Smallest Hückel Aromatic into π-Conjugated Polymers". J. Org. Chem. 76 (15): 5689–5696. doi:10.1021/jo101108f. PMID 20704438.
  6. Hollis, J. M.; Remijan, Anthony J.; Jewell, P. R.; Lovas, F. J. (2006-05-10). "Cyclopropenone (c-H 2 C 3 O): A New Interstellar Ring Molecule". The Astrophysical Journal. 642 (2): 933–939. doi:10.1086/501121. ISSN 0004-637X.