Cyclopentanone

Last updated
Cyclopentanone [1]
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Cyclopentanone Cyclopentanone.png
Cyclopentanone
AW Cyclopentanone.jpg
Names
Preferred IUPAC name
Cyclopentanone
Other names
Ketocyclopentane
Adipic ketone
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.033 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
RTECS number
  • GY4725000
UNII
  • InChI=1S/C5H8O/c6-5-3-1-2-4-5/h1-4H2 Yes check.svgY
    Key: BGTOWKSIORTVQH-UHFFFAOYSA-N Yes check.svgY
  • 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
Appearanceclear, 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:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg
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.

Contents

Preparation

Ketonic decarboxylation of adipic acid gives cyclopentanone. The reaction is conducted at elevated temperatures in the presence of barium hydroxide. [3]

Barium adipate pyrolysis.png

The Pd-catalyzed oxidation of cyclopentene also gives cyclopentanone. [4]

Uses

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 Cyclopal.svg
Cyclopentobarbital, a drug made from cyclopentanone

Cyclopentanone is also used to make cyclopentamine, the pesticide pencycuron, and pentethylcyclanone. [6]

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

  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. 1 2 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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