Cyclopentanone
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| Names | |||
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| Preferred IUPAC name
Cyclopentanone | |||
| Other names
Ketocyclopentane
Adipic ketone | |||
| Identifiers | |||
3D model (JSmol)
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| KEGG | |||
PubChem CID
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| UNII | |||
CompTox Dashboard (EPA)
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| 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
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cyclohexanone 2-pentanone 3-pentanone cyclopentenone | ||
Related compounds
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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
[edit | edit source]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
[edit | edit source]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,[6] and pentethylcyclanone.
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
[edit | edit source]- ^ Merck Index, 11th Edition, 2748.
- ^ Sigma-Aldrich Co., Cyclopentanone.
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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.Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
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