Cyclopentanone

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Cyclopentanone[1]
Cyclopentanone
Cyclopentanone-3D-balls-by-AHRLS-2012.png
Cyclopentanol-Space-filling-by-AHRLS-2012.png
Names
Preferred IUPAC name
Cyclopentanone
Other names
Ketocyclopentane
Adipic ketone
Identifiers
3D model (Jmol)
ChEBI
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". Org. Synth. 5: 37. ; Coll. Vol., 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 "Ketones" in Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim.doi:10.1002/14356007.a15_077