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C112402

Sigma-Aldrich

Cyclopentanone

ReagentPlus®, ≥99%

Synonym(s):

Adipic ketone

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About This Item

Linear Formula:
C5H8(=O)
CAS Number:
Molecular Weight:
84.12
Beilstein:
605573
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.21

Quality Level

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

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

86.0 °F - closed cup

Flash Point(C)

30 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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)
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)
Cyclopentanone as a Cation-Stabilizing Electron-Pair Donor in the Calcium-Catalyzed Intermolecular Carbohydroxylation of Alkynes.
Stopka T and Niggemann M.
Organic Letters, 17(6), 1437-1440 (2015)
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)

Articles

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

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

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

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

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