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C112909

Sigma-Aldrich

2-Cyclopenten-1-one

98%

Empirical Formula (Hill Notation):
C5H6O
CAS Number:
Molecular Weight:
82.10
Beilstein:
1446054
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

98%

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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Related Categories

Application

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

Packaging

5, 25, 100 g in glass bottle

Pictograms

Flame

Signal Word

Warning

Hazard Statements

Hazard Classifications

Flam. Liq. 3

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

107.6 °F - closed cup

Flash Point(C)

42 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Certificate of Origin

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%
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)
Xiaoxun Li et al.
Organic letters, 14(6), 1584-1587 (2012-03-03)
Functionalized cyclopentenones were synthesized by a Rh-catalyzed carbonylation of 3-acyloxy-1,4-enynes, derived from alkynes and α,β-unsaturated aldehydes. The reaction involved a Saucy-Marbet 1,3-acyloxy migration of propargyl esters and a [4 + 1] cycloaddition of the resulting acyloxy substituted vinylallene with CO.
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
Daniel J Kerr et al.
Organic letters, 14(7), 1732-1735 (2012-03-30)
Oxazolidinones are powerful promoters of the Nazarov reaction, enabling the cyclization of conventionally resistant substrates to be achieved under mild conditions. They exert excellent regio- and torquoselective control in both the conventional Nazarov reaction giving cyclopentenones and in the "interrupted"

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