2-CYCLOPENTYLIDENECYCLOPENTANONE Chemical Properties

Melting point:

74-75 °C

Boiling point:

231.78°C (rough estimate)

Density 

1 g/cm³

refractive index 

1.5215 (estimate)

Flash point:

104°C

storage temp. 

2-8°C, protect from light

Appearance

Colorless to light yellow Liquid

InChI

InChI=1S/C10H14O/c11-10-7-3-6-9(10)8-4-1-2-5-8/h1-7H2

InChIKey

NYSYNXRPXJZYFY-UHFFFAOYSA-N

SMILES

C1(=O)CCC/C/1=C1\CCCC\1

MSDS

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2-CYCLOPENTYLIDENECYCLOPENTANONE Usage And Synthesis

Uses

Bicyclopentylidene-2-one is derived from Cyclopentanone (C988395), which is a chemical compound used in the synthesis of various simple and complex organic compounds. Also, it is used in the synthesis of peptidase IV inhibitors for the treatment of type 2 diabetes.

Synthesis Reference(s)

The Journal of Organic Chemistry, 39, p. 1028, 1974 DOI: 10.1021/jo00922a002

Synthesis

The synthesis of 2-cyclopentylidenecyclopentanone is a classic example of a self-condensation reaction, specifically an aldol condensation followed by dehydration. Under basic or acidic conditions, one molecule of cyclopentanone (C₅H₈O) is converted into its enolate, which nucleophilically attacks the carbonyl group of a second cyclopentanone molecule. The resulting β-hydroxy ketone intermediate undergoes dehydration to yield the α,β-unsaturated ketone product. Industrially, such transformations are often conducted under heterogeneous catalysis using solid acid–base bifunctional catalysts (e.g., Mg–Al hydrotalcites or mixed metal oxides) to improve selectivity and enable continuous-flow operation. The product is of interest as a model intermediate for high-density fuel candidates and has been explored in fragrance chemistry for its woody, amber-like odor.

2-CYCLOPENTYLIDENECYCLOPENTANONE(825-25-2)Related Product Information

• 1-Indanone
• Cyclobutanone
• METHYLENECYCLOPENTANE
• 2-CYCLOPENTYLIDENECYCLOPENTANONE
• 2-ETHYL-2-HEXENAL
• ETHYLIDENECYCLOPENTANE
• Cyclopentanone
• 2,5-BIS(CYCLOPENTYLLIDENE)CYCLOPENTANONE-1
• 2-PROPYL-2-HEPTENAL
• 3-Cyclopentylidenecyclopentanone
• CYCLOPENTYLIDENECYCLOPENTANE
• 3-METHYL-3-HEPTEN-2-ONE