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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
assay:
≥99%
bp:
130-131 °C (lit.)

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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.)

functional group

ketone

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.[1] Microwave spectra of cyclopentanone has been reported.[2] Transformation of furfural (FFA) to cyclopentanone (CPO) by various methods has been reported.[3][4][5] Unimolecular degradation pathways of cyclopentanone have been studied.[6]

Application

Cyclopentanone was used to design an absorbing fluorescent filter for fluorescent imaging system.[7]
It may be used in the following studies:
  • Preparation of (2E,5E)-2,5-bis(4-(azidomethyl)benzylidene) cyclopentanone, via cross-aldol condensation.[8]
  • Preparation of symmetrical C-5 curcuminoids by reacting with substituted benzaldehyde via Claisen-Schmidt condensation.[9]
  • As an electron pair donor to stabilize allyl and vinyl cations during intramolecular carbohydroxylation of alkynes.[10]

Legal Information

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

pictograms

FlameExclamation mark
GHS02,GHS07

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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)
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)
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)
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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