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: FlammableGHS07: 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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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 is 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 octonitrocubane.[6]

References

  1. ^ Merck Index, 11th Edition, 2748.
  2. ^ Sigma-Aldrich Co., Cyclopentanone.
  3. ^ J. F. Thorpe and G. A. R. Kon (1925). "Cyclopentanone". Organic Syntheses. 5: 37.; Collective Volume, 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
  5. ^ a b Hardo Siegel; Manfred Eggersdorfer (2005). "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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