Cyclopentanone

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Cyclopentanone[1]
Cyclopentanone
Cyclopentanone-3D-balls-by-AHRLS-2012.png
Names
Preferred IUPAC name
Cyclopentanone
Other names
Ketocyclopentane
Adipic ketone
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.033
KEGG
RTECS number GY4725000
UNII
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
Safety data sheet Cyclopentanone
Flash point 26 °C (79 °F; 299 K)
Related compounds
Related ketones
cyclohexanone
2-pentanone
3-pentanone
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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Infobox references

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

Preparation[edit]

Upon treatment with barium hydroxide at elevated temperatures, adipic acid undergoes ketonization to give cyclopentanone:[2]

(CH2)4(CO2H)2 → (CH2)4CO + H2O + CO2

Uses[edit]

Cyclopentanone is common precursor to fragrances, especially those related to jasmine and jasmone. Examples include 2-pentyl- and 2-heptylcyclopentanone.[3] It is a versatile synthetic intermediate, being a precursor to cyclopentobarbital.[4]

Cyclopentobarbital is a drug made from cyclopentanone.

Cyclopentanone is also used to make cyclopentamine, the pesticide pencycuron, and pentethylcyclanone.[4]

References[edit]

  1. ^ Merck Index, 11th Edition, 2748.
  2. ^ J. F. Thorpe and G. A. R. Kon (1925). "Cyclopentanone". Organic Syntheses. 5: 37. ; Collective Volume, 1, p. 192 .
  3. ^ 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
  4. ^ a b Hardo Siegel, Manfred Eggersdorfer (2005). "Ketones". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a15_077.