Cyclopentanone

Cyclopentanone^[1]

Names
Preferred IUPAC name Cyclopentanone
Other names Ketocyclopentane Adipic ketone
Identifiers
CAS Number	120-92-3 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:16486 Y
ChEMBL	ChEMBL18620 Y
ChemSpider	8141 Y
ECHA InfoCard	100.004.033
KEGG	C00557 Y
PubChem	8452
RTECS number	GY4725000
UNII	220W81TN3S Y
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
Hazards
Safety data sheet	Cyclopentanone
Flash point	26 °C (79 °F; 299 K)
Related compounds
Related ketones	cyclohexanone 2-pentanone 3-pentanone
Related compounds	cyclopropane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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

Preparation

Upon treatment with barium hydroxide at elevated temperatures, adipic acid undergoes ketonization to give cyclopentanone:^[2]

(CH₂)₄(CO₂H)₂ → (CH₂)₄CO + H₂O + CO₂

Uses

Cyclopentanone is common precursor to fragrances, especially those related to jasmine and jasmone. Examples include 2-pentyl- and 2-heptylcyclopentanone.^[3] It is a versatile synthetic intermediate, being a precursor to cyclopentobarbital.^[4]

Cyclopentobarbital is a drug made from cyclopentanone.

Cyclopentanone is also used to make cyclopentamine, the pesticide pencycuron, and pentethylcyclanone.^[4]

References