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C112402

Sigma-Aldrich

Cyclopentanone

ReagentPlus®, ≥99%

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Synonym(s):
Adipic ketone
Linear Formula:
C5H8(=O)
CAS Number:
120-92-3
Molecular Weight:
84.12
Beilstein:
605573
EC Number:
204-435-9
MDL number:
MFCD00001409
UNSPSC Code:
12352100
PubChem Substance ID:
24892352
NACRES:
NA.21

Quality Level

200

product line

ReagentPlus®

Assay

≥99%

form

liquid

refractive index

n20/D 1.437 (lit.)

bp

130-131 °C (lit.)

mp

−51 °C (lit.)

density

0.951 g/mL at 25 °C (lit.)

SMILES string

O=C1CCCC1

InChI

1S/C5H8O/c6-5-3-1-2-4-5/h1-4H2

InChI key

BGTOWKSIORTVQH-UHFFFAOYSA-N

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General description

Cyclopentanone is cyclic ketone. Baeyer-Villiger-oxidation of cyclopentanone using aqueous hydrogen peroxide containing 30% H2O2, solid acid catalysts has been studied. Microwave spectra of cyclopentanone has been reported. Transformation of furfural (FFA) to cyclopentanone (CPO) by various methods has been reported. Unimolecular degradation pathways of cyclopentanone have been studied.

Application

Cyclopentanone was used to design an absorbing fluorescent filter for fluorescent imaging system.
It may be used in the following studies:
  • Preparation of (2E,5E)-2,5-bis(4-(azidomethyl)benzylidene) cyclopentanone, via cross-aldol condensation.
  • Preparation of symmetrical C-5 curcuminoids by reacting with substituted benzaldehyde via Claisen-Schmidt condensation.
  • As an electron pair donor to stabilize allyl and vinyl cations during intramolecular carbohydroxylation of alkynes.

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Warning

Hazard Statements

H226,H315,H319

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2

WGK

WGK 1

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Efficient and selective hydrogenation of biomass-derived furfural to cyclopentanone using Ru catalysts.
Fang R, et al.
Green Chemistry, 17(8), 4183-4188 (2015)
Antibacterial and antioxidant activity evaluation of novel symmetrical and unsymmetrical C5-curcuminoids.
Manohar S, et al.
Indian Journal of Chemistry, 54, 1235-1246 (2015)
Giga-pixel fluorescent imaging over an ultra-large field-of-view using a flatbed scanner.
Gorocs Z, et al.
Lab on a chip, 13(22), 4460-4466 (2013)
Ring Puckering in Five-Membered Rings. III. The Microwave Spectrum, Dipole Moment, and Structure of Cyclopentanone.
Kim H and Gwinn WD.
J. Chem. Phys. , 51(5), 181519-181519 (1969)
Computational Kinetic Study for the Unimolecular Decomposition of Cyclopentanone.
Zaras AM, et al.
International Journal of Chemical Kinetics, 47(7), 439-446 (2015)
View All Related Papers

Articles

Aldol Condensation Reaction

The aldol condensation reaction is an organic reaction introduced by Charles Wurtz, who first prepared the β-hydroxy aldehyde from acetaldehdye in 1872.

Baeyer-Villiger Oxidation Reaction

The Baeyer-Villiger oxidation is the oxidative cleavage of a carbon-carbon bond adjacent to a carbonyl, which converts the ketones to esters and the cyclic ketones to lactones.

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