Cyclopentanone

Cyclopentanone is the organic compound with the formula (CH₂)₄CO. This cyclic ketone is a colorless volatile liquid.

Cyclopentanone^[1]

Cyclopentanone
Names
Preferred IUPAC name Cyclopentanone
Other names Ketocyclopentane Adipic ketone
Identifiers
CAS Number	120-92-3 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:16486 Y
ChEMBL	ChEMBL18620 Y
ChemSpider	8141 Y
ECHA InfoCard	100.004.033
KEGG	C00557 Y
PubChem CID	8452
RTECS number	GY4725000
UNII	220W81TN3S Y
CompTox Dashboard (EPA)	DTXSID3029154
InChI InChI=1S/C5H8O/c6-5-3-1-2-4-5/h1-4H2 Y Key: BGTOWKSIORTVQH-UHFFFAOYSA-N Y InChI=1/C5H8O/c6-5-3-1-2-4-5/h1-4H2 Key: BGTOWKSIORTVQH-UHFFFAOYAP
SMILES C1CCC(=O)C1
Properties
Chemical formula	C5H8O
Molar mass	84.12 g/mol
Appearance	clear, colorless liquid
Odor	peppermint-like
Density	0.95 g/cm3, liquid
Melting point	−58.2 °C (−72.8 °F; 215.0 K)
Boiling point	130.6 °C (267.1 °F; 403.8 K)
Solubility in water	Slightly soluble
Magnetic susceptibility (χ)	−51.63·10−6 cm3/mol
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H226, H315, H319
Precautionary statements	P210, P302+P352, P305+P351+P338[2]
Flash point	26 °C (79 °F; 299 K)
Safety data sheet (SDS)	Cyclopentanone
Related compounds
Related ketones	cyclohexanone 2-pentanone 3-pentanone cyclopentenone
Related compounds	cyclopropane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

Preparation

Ketonic decarboxylation of adipic acid gives cyclopentanone. The reaction is conducted at elevated temperatures in the presence of barium hydroxide.^[3]

The Pd-catalyzed oxidation of cyclopentene also gives cyclopentanone.^[4]

Uses

Cyclopentanone is common precursor to fragrances, especially those related to jasmine and jasmone. Examples include 2-pentyl- and 2-heptylcyclopentanone.^[5] It is a versatile synthetic intermediate, being a precursor to cyclopentobarbital.^[6]

Cyclopentobarbital, a drug made from cyclopentanone

Cyclopentanone is also used to make cyclopentamine, the pesticide pencycuron, and pentethylcyclanone.^[6]

It is also used as a precursor to cubane-1,4-dicarboxylate, which is used to synthesize other substituted cubanes, such as the high explosives heptanitrocubane and octanitrocubane.^[7]