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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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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 Germany

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

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...
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...
Jesse R Poganik et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 33(12), 14636-14652 (2019-11-02)
The nuclear factor erythroid 2-related factor 2 (Nrf2) signaling axis is a target of covalent drugs and bioactive native electrophiles. However, much of our understanding of Nrf2 regulation has been focused at the protein level. Here we report a post-transcriptional...
Tetrahedron Letters, 34, 6777-6777 (1993)
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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