Cyclopentanone

Cyclopentanone^[1]
Names
	Preferred IUPAC name Cyclopentanone
	Other names Ketocyclopentane; Adipic ketone
Identifiers
CAS Number	120-92-3 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:16486 ;
ChEMBL	ChEMBL18620 ;
ChemSpider	8141 ;
ECHA InfoCard	100.004.033
KEGG	C00557 ;
PubChem CID	8452;
RTECS number	GY4725000;
UNII	220W81TN3S ;
CompTox Dashboard (EPA)	DTXSID3029154 ;
	InChI InChI=1S/C5H8O/c6-5-3-1-2-4-5/h1-4H2 Key: BGTOWKSIORTVQH-UHFFFAOYSA-N ; 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
Flash point	26 °C (79 °F; 299 K)
Safety data sheet (SDS)	Cyclopentanone
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). verify (what is ?) 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

^ Merck Index, 11th Edition, 2748.
^ J. F. Thorpe and G. A. R. Kon (1925). "Cyclopentanone". Organic Syntheses. 5: 37; Collected Volumes, vol. 1, p. 192..
^ Johannes Panten and Horst Surburg "Flavors and Fragrances, 2. Aliphatic Compounds" in Ullmann's Encyclopedia of Industrial Chemistry, 2015, Wiley-VCH, Weinheim.doi:10.1002/14356007.t11_t01
^ ^a ^b Hardo Siegel, Manfred Eggersdorfer "Ketones" in Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim.doi:10.1002/14356007.a15_077

[1] Merck Index, 11th Edition, 2748.

[2] J. F. Thorpe and G. A. R. Kon (1925). "Cyclopentanone". Organic Syntheses. 5: 37; Collected Volumes, vol. 1, p. 192..

[3] Johannes Panten and Horst Surburg "Flavors and Fragrances, 2. Aliphatic Compounds" in Ullmann's Encyclopedia of Industrial Chemistry, 2015, Wiley-VCH, Weinheim.doi:10.1002/14356007.t11_t01

[Ullmann-4] Hardo Siegel, Manfred Eggersdorfer "Ketones" in Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim.doi:10.1002/14356007.a15_077

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