Cyclopentanone is the

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

with the formula (CH₂)₄CO. This cyclic

ketone In organic chemistry, a ketone is an organic compound with the structure , where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (a carbon-oxygen double bond C=O). The simplest ketone is acetone ( ...

is a colorless volatile liquid.

Preparation

Ketonic decarboxylation Ketonic decarboxylation (also known as decarboxylative ketonization) is a type of organic reaction involving decarboxylation, converting two equivalents of a carboxylic acid () to a symmetric ketone (). The reaction typically requires heat and a ...

adipic acid Adipic acid or hexanedioic acid is the organic compound with the formula C6H10O4. It a white crystalline powder at standard temperature and pressure. From an industrial perspective, it is the most important dicarboxylic acid at about 2.5 billion ...

gives cyclopentanone. The reaction is conducted at elevated temperatures in the presence of

barium hydroxide Barium hydroxide is a chemical compound with the chemical formula Ba(OH)2. The monohydrate (''x'' = 1), known as baryta or baryta-water, is one of the principal compounds of barium. This white granular monohydrate is the usual commercial form. ...

. :

The Pd-catalyzed oxidation of

cyclopentene Cyclopentene is a chemical compound with the formula . It is a colorless liquid with a petrol-like odor. It has few applications, and thus is mainly used as a minor component of gasoline, present in concentrations of less than 1%. It is one of t ...

also gives cyclopentanone.

Uses

Cyclopentanone is common precursor to fragrances, especially those related to

jasmine Jasmine (botanical name: ''Jasminum'', pronounced ) is a genus of shrubs and vines in the olive family of Oleaceae. It contains around 200 species native to tropical and warm temperate regions of Eurasia, Africa, and Oceania. Jasmines are wid ...

and

jasmone Jasmone is an organic compound, which is a volatile portion of the oil from jasmine flowers. It is a colorless to pale yellow liquid. Jasmone can exist in two isomeric forms with differing geometry around the pentenyl double bond, ''cis''-jasmon ...

. Examples include 2-pentyl- and 2-heptylcyclopentanone. It is a versatile synthetic intermediate, being a precursor to

cyclopentobarbital Cyclopentobarbital sodium (Cyclopal, Dormisan) is a barbiturate derivative invented in the 1940s. It has sedative and anticonvulsant properties, and was used primarily as an anaesthetic in veterinary medicine. Cyclopal is considered similar in ...

Cyclopentanone is also used to make

cyclopentamine Cyclopentamine (trade names Clopane, Cyclonarol, Cyclosal, Cyklosan, Nazett, Sinos, among others) is a sympathomimetic and vasoconstrictor drug of the alkylamine family and related to the arylalkylamines. Cyclopentamine was indicated in the pa ...

, the pesticide pencycuron, and

pentethylcyclanone Pentethylcyclanone is an antitussive medication Medication (also called medicament, medicine, pharmaceutical drug, medicinal product, medicinal drug or simply drug) is a drug used to medical diagnosis, diagnose, cure, treat, or preventi ...

. It is also used as a precursor to

cubane Cubane is a synthetic hydrocarbon compound with the Chemical formula, formula . It consists of eight carbon atoms arranged at the corners of a Cube (geometry), cube, with one hydrogen atom attached to each carbon atom. A solid crystalline substanc ...

-1,4-dicarboxylate, which is used to synthesize other substituted cubanes, such as the high explosives

heptanitrocubane Heptanitrocubane is an experimental high explosive based on the cubic eight-carbon cubane molecule and closely related to octanitrocubane. Seven of the eight hydrogen atoms at the corners of the cubane molecule are replaced by nitro groups, giv ...

and

octanitrocubane Octanitrocubane (molecular formula: C8(NO2)8) is a proposed high explosive that, like TNT, is shock-insensitive (not readily detonated by shock). The octanitrocubane molecule has the same chemical structure as cubane (C8H8) except that each of th ...

References

{{Authority control 5 Ketone solvents Perfume ingredients Cyclopentanes