C112909
2-Cyclopenten-1-one
98%
Synonym(s):
1-Cyclopenten-5-one, 1-Cyclopenten-3-one, 2-Cyclopentenone, Cyclopent-2-en-1-one, Cyclopenten-3-one
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About This Item
Empirical Formula (Hill Notation):
C5H6O
CAS Number:
Molecular Weight:
82.10
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
213-213-0
Beilstein/REAXYS Number:
1446054
MDL number:
Assay:
98%
Form:
liquid
InChI key
BZKFMUIJRXWWQK-UHFFFAOYSA-N
InChI
1S/C5H6O/c6-5-3-1-2-4-5/h1,3H,2,4H2
SMILES string
O=C1CCC=C1
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
Quality Level
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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.
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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)
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
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)
Filippo De Simone et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 17(51), 14527-14538 (2011-11-25)
The Nazarov cyclization of divinyl ketones gives access to cyclopentenones. Replacing one of the vinyl groups by a cyclopropane leads to a formal homo-Nazarov process for the synthesis of cyclohexenones. In contrast to the Nazarov reaction, the cyclization of vinyl-cyclopropyl
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