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Cyclopentanone

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Cyclopentanone[1]
Cyclopentanone
Cyclopentanone
Names Preferred IUPAC name
Cyclopentanone
Other names
Ketocyclopentane
Adipic ketone
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.033 Edit this at Wikidata KEGG
RTECS number
  • GY4725000
UNII
  • InChI=1S/C5H8O/c6-5-3-1-2-4-5/h1-4H2 checkY
    Key: BGTOWKSIORTVQH-UHFFFAOYSA-N checkY
  • InChI=1/C5H8O/c6-5-3-1-2-4-5/h1-4H2
    Key: BGTOWKSIORTVQH-UHFFFAOYAP
  • C1CCC(=O)C1
Properties 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) Slightly soluble −51.63·10−6 cm3/mol Hazards GHS labelling: GHS02: Flammable GHS07: Exclamation mark Warning H226, H315, H319 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).
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Chemical compound

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

Preparation

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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

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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,[6] 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.[7]

References

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  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. ^ Claus, Martin; Claus, Evelyn; Claus, Peter; Hönicke, Dieter; Födisch, Ringo; Olson, Michael (2016). "Cyclopentadiene and Cyclopentene". Ullmann's Encyclopedia of Industrial Chemistry. pp. 1–16. doi:10.1002/14356007.a08_227.pub2. ISBN 978-3-527-30673-2.
  5. ^ 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
  6. ^ 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.
  7. ^ 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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