Cyclopentanone
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| Template:Longitem | C5H8O |
| Molar mass | 84.12 g/mol |
| Appearance | clear, colorless liquid |
| Odor | peppermint-like |
| Density | 0.95 g/cm3, liquid |
| Melting point | Template:Chembox CalcTemperatures |
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| Template:Longitem | −51.63·10−6 cm3/mol |
| Flash point | Template:Chembox CalcTemperatures |
| Template:Longitem | cyclohexanone 2-pentanone 3-pentanone cyclopentenone |
| Template:Longitem | cyclopropane |
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Cyclopentanone is the organic compound with the formula (CH2)4CO. This cyclic ketone is a colorless volatile liquid.
Preparation
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
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]
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
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- ↑ Merck Index, 11th Edition, 2748.
- ↑ Sigma-Aldrich Co., Cyclopentanone.
- ↑ Script error: No such module "Citation/CS1".
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- ↑ Johannes Panten and Horst Surburg "Flavors and Fragrances, 2. Aliphatic Compounds" in Ullmann's Encyclopedia of Industrial Chemistry, 2015, Wiley-VCH, Weinheim.Script error: No such module "CS1 identifiers".
- ↑ a b Script error: No such module "citation/CS1".
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