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C112909

Sigma-Aldrich

2-Cyclopenten-1-one

98%

Synonym(s):

1-Cyclopenten-3-one, 1-Cyclopenten-5-one, 2-Cyclopentenone, Cyclopent-2-en-1-one, Cyclopenten-3-one

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5 G
$84.60
25 G
$201.00
100 G
$613.00

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Estimated to ship onMarch 17, 2025


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5 G
$84.60
25 G
$201.00
100 G
$613.00

About This Item

Empirical Formula (Hill Notation):
C5H6O
CAS Number:
Molecular Weight:
82.10
Beilstein/REAXYS Number:
1446054
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
form:
liquid
assay:
98%

$84.60


Estimated to ship onMarch 17, 2025


Request a Bulk Order

Quality Level

assay

98%

form

liquid

refractive index

n20/D 1.481 (lit.)

bp

64-65 °C/19 mmHg (lit.)

density

0.98 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

O=C1CCC=C1

InChI

1S/C5H6O/c6-5-3-1-2-4-5/h1,3H,2,4H2

InChI key

BZKFMUIJRXWWQK-UHFFFAOYSA-N

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Application

Versatile electrophile employed in a variety of addition reactions including conjugate addition of organocopper nucleophiles,[1] Michael reaction with silyl enol ethers,[2] and siloxanes,[3] Diels-Alder cycloadditions,[4] and phosphoniosilylations.[5]

pictograms

Flame

signalword

Warning

hcodes

Hazard Classifications

Flam. Liq. 3

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

107.6 °F - closed cup

flash_point_c

42 °C - closed cup

ppe

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


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Brett D Schwartz et al.
Organic letters, 15(8), 1934-1937 (2013-04-05)
The title natural product, 1, has been synthesized in 20 steps from the enantiomerically pure cis-1,2-dihydrocatechol 2, itself obtained through the whole-cell biotransformation of toluene. The pivotal steps in the reaction sequence involve a Diels-Alder cycloaddition reaction between diene 2
Diverse reactivity in a rhodium(III)-catalyzed oxidative coupling of N-allyl arenesulfonamides with alkynes.
Dongqi Wang et al.
Angewandte Chemie (International ed. in English), 51(49), 12348-12352 (2012-10-31)
Rachel Lerebours et al.
Organic letters, 9(14), 2737-2740 (2007-06-15)
Palladium-phosphinous acids catalyze the conjugate addition of arylsiloxanes to a wide range of alpha,beta-unsaturated substrates in water. A microwave-assisted procedure is described that uses 5 mol % of POPd1 to afford beta-substituted ketones, aldehydes, esters, nitriles, and nitroalkanes in 83%
Tetrahedron Letters, 34, 6777-6777 (1993)
Marc Revés et al.
Organic letters, 14(13), 3534-3537 (2012-06-28)
1,2,3,4-Tetramethyl-bicyclo[2.2.1]hepta-2,5-diene (TMNBD, for tetramethylnorbornadiene) has been prepared and used successfully as an acetylene equivalent in the synthesis of substituted cyclopentenones. TMNBD is easily accessible on a multigram scale and displays excellent reactivity toward the intermolecular Pauson-Khand reaction. Conjugate additions on

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