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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:
120-92-3
Molecular Weight:
84.12
Beilstein/REAXYS Number:
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

signalword

Warning

Hazard Classifications

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

Storage Class

3 - Flammable liquids

wgk_germany

WGK 1

flash_point_f

86.0 °F - closed cup

flash_point_c

30 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
STBL2466
STBL0184
STBL0509
STBK6286
STBJ8884

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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)
Selective conversion of furfural to cyclopentanone or cyclopentanol using different preparation methods of Cu-Co catalysts.
Li XL, et al.
Green Chemistry, 17(2), 1038-1046 (2015)
Carbon supported Pd-Cu catalysts for highly selective rearrangement of furfural to cyclopentanone.
Hronec M, et al.
Applied Catalysis. B, Environmental, 181, 210-219 (2016)
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)
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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