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825-25-2

825-25-2 Structure

825-25-2 Structure
IdentificationBack Directory
[Name]

2-CYCLOPENTYLIDENECYCLOPENTANONE
[CAS]

825-25-2
[Synonyms]

Loxoprofen Impurity 61
Bicyclopentyliden-2-one
BICYCLOPENTYLIDENE-2-ONE
Δ1,1'-Bicyclopentane-2-one
Δ1,1'-Bi[cyclopentane]-2-one
2-CYCLOPENTYLIDENECYCLOPENTANONE
1,1'-Bi(cyclopentylidene)]-2-one
cyclopentylidenecyclopentan-2-one
Cyclopentanone,2-cyclopentylidene-
2-CYCLOPENTYLIDENE-1-CYCLOPENTANONE
2-Cyclopentylidenecyclopentane-1-one
2-Cyclopentylidenecyclopentanone,97%
[EINECS(EC#)]

212-542-7
[Molecular Formula]

C10H14O
[MDL Number]

MFCD00044678
[MOL File]

825-25-2.mol
[Molecular Weight]

150.22
Chemical PropertiesBack Directory
[Melting point ]

74-75 °C
[Boiling point ]

231.78°C (rough estimate)
[density ]

1 g/cm3
[refractive index ]

1.5215 (estimate)
[Fp ]

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
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H315
[Precautionary statements ]

P264-P280-P302+P352-P321-P332+P313-P362
Hazard InformationBack Directory
[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.
Spectrum DetailBack Directory
[Spectrum Detail]

2-CYCLOPENTYLIDENECYCLOPENTANONE(825-25-2)1HNMR
2-CYCLOPENTYLIDENECYCLOPENTANONE(825-25-2)IR1
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