Cyclopropenone information

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 ;
3D model (JSmol)	Interactive image;
ChemSpider	121433;
PubChem CID	137779;
UNII	5MPZ6QZ6ZF ;
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

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. It is an aromatic compound.^[4]^[5]

^ R. Breslow, J. Pecoraro, T. Sugimoto "Cyclpropenone" Org. Synth. 1977, vol. 57, pp. 41. doi:10.15227/orgsyn.057.0041
^ Breslow, Ronald; Oda, Masaji (1972-06-01). "Isolation and characterization of pure cyclopropenone". Journal of the American Chemical Society. 94 (13): 4787–4788. doi:10.1021/ja00768a089. ISSN 0002-7863.
^ Elliott, Gregory I.; Boger, Dale L. "Cyclopropene, 3,3‑Dimethoxy". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rn00486. Dimethyl cyclopropenone ketal is less stable than the corresponding cyclic ketal derivatives....A direct route to cyclopropenone is the hydrolysis of 3,3‑dimethoxycyclopropene.
^ "Experiments show cyclopropenone is aromatic". Chem. Eng. News. 61 (38): 33. 1983. doi:10.1021/cen-v061n038.p033.
^ 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.

[1] R. Breslow, J. Pecoraro, T. Sugimoto "Cyclpropenone" Org. Synth. 1977, vol. 57, pp. 41. 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. doi:10.1021/ja00768a089. ISSN 0002-7863.

[3] Elliott, Gregory I.; Boger, Dale L. "Cyclopropene, 3,3‑Dimethoxy". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rn00486. 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.

Cyclopropenone information

and 29 Related for: Cyclopropenone information

Cyclopropenone

C3H2O

Water

Potassium chloride

Nitrous oxide

Sodium chloride

Carbon dioxide

Organic compound

Life

Ammonia

Molecule

Outer space

Abiogenesis

Acetic acid

Nitrogen

Benzene

Extraterrestrial life

Graphene

Deuterium

Methane

Chemical formula

Ethanol

Methanol

Acetaldehyde

Carbon monoxide

Ozone

Potassium cyanide

Hydrogen peroxide

Titanium dioxide

Names

Main resonance structures of cyclopropenone.

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