Cyclopentanone

Cyclopentanone^[1]
	Cyclopentanone
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
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
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). 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:^[3]

(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.^[4] It is a versatile synthetic intermediate, being a precursor to cyclopentobarbital.^[5]

Cyclopentobarbital, a drug made from cyclopentanone

Cyclopentanone is also used to make cyclopentamine, the pesticide pencycuron, and pentethylcyclanone.^[5]

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.^[6]

References

^ Merck Index, 11th Edition, 2748.
^ Sigma-Aldrich Co., Cyclopentanone.
^ 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 (2005). "Ketones". Ketones. Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a15_077. ISBN 978-3-527-30673-2.
^ Bliese, Marianne; Tsanaktsidis, John (1997). "Dimethyl Cubane-1,4-dicarboxylate: A Practical Laboratory Scale Synthesis". Australian Journal of Chemistry. 50 (3): 189. doi:10.1071/C97021. ISSN 0004-9425.

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

[sigma-2] Sigma-Aldrich Co., Cyclopentanone.

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

[4] 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-5] Hardo Siegel; Manfred Eggersdorfer (2005). "Ketones". Ketones. Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a15_077. ISBN 978-3-527-30673-2.

[6] Bliese, Marianne; Tsanaktsidis, John (1997). "Dimethyl Cubane-1,4-dicarboxylate: A Practical Laboratory Scale Synthesis". Australian Journal of Chemistry. 50 (3): 189. doi:10.1071/C97021. ISSN 0004-9425.

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