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Cyclopentanone

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Cyclopentanone
Cyclopentanone
Cyclopentanone
Names
Preferred IUPAC name Cyclopentanone
Other names Ketocyclopentane
Adipic ketone
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.033 Edit this at Wikidata
KEGG
PubChem CID
RTECS number
  • GY4725000
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H8O/c6-5-3-1-2-4-5/h1-4H2Key: BGTOWKSIORTVQH-UHFFFAOYSA-N
  • InChI=1/C5H8O/c6-5-3-1-2-4-5/h1-4H2Key: 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/cm, 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 cm/mol
Hazards
GHS labelling:
Pictograms GHS02: FlammableGHS07: Exclamation mark
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 , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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

Preparation

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

Uses

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

Cyclopentobarbital, a drug made from cyclopentanone

Cyclopentanone is also used to make cyclopentamine, the pesticide pencycuron, and pentethylcyclanone.

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.

References

  1. Merck Index, 11th Edition, 2748.
  2. Sigma-Aldrich Co., Cyclopentanone.
  3. Thorpe, J. F.; Kon, G. A. R. (1925). "Cyclopentanone". Org. Synth. 5: 37. doi:10.15227/orgsyn.005.0037.
  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
  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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