C112909
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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About This Item
Empirical Formula (Hill Notation):
C5H6O
CAS Number:
Molecular Weight:
82.10
Beilstein:
1446054
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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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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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.
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
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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
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)
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"
Yoshihiro Sumiyoshi et al.
The Journal of chemical physics, 125(12), 124307-124307 (2006-10-04)
Pure rotational transitions in the ground state for Ar-OH and Ar-OD [Y. Ohshima et al., J. Chem. Phys. 95, 7001 (1991) and Y. Endo et al., Faraday Discuss. 97, 341 (1994)], those in the excited states of the OH vibration
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