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C102814

Sigma-Aldrich

2-Cyclohexen-1-one

≥95%

Synonym(s):

1-Cyclohexen-3-one, 2-Cyclohexenone, 3-Oxocyclohexene, Cyclohexen-3-one, Cyclohexenone

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About This Item

Linear Formula:
C6H8(=O)
CAS Number:
930-68-7
Molecular Weight:
96.13
Beilstein/REAXYS Number:
1280477
EC Number:
213-223-5
MDL number:
MFCD00001577
UNSPSC Code:
12352100
PubChem Substance ID:
24892309
NACRES:
NA.22

vapor pressure

760 mmHg ( 168 °C)

assay

≥95%

form

liquid

refractive index

n20/D 1.488 (lit.)

bp

171-173 °C (lit.)

mp

−53 °C (lit.)

density

0.993 g/mL at 25 °C (lit.)

SMILES string

O=C1CCCC=C1

InChI

1S/C6H8O/c7-6-4-2-1-3-5-6/h2,4H,1,3,5H2

InChI key

FWFSEYBSWVRWGL-UHFFFAOYSA-N

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Application

Versatile electrophile employed in a range of addition reactions including conjugate addition of organocopper nucleophiles, Michael reaction with enol silanes, and phosphoniosilylations.

pictograms

FlameSkull and crossbones
GHS02,GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 1 Inhalation - Acute Tox. 2 Dermal - Acute Tox. 3 Oral - Flam. Liq. 3

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

132.8 °F - closed cup

flash_point_c

56 °C - closed cup

ppe

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

Certificates of Analysis (COA)

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Tetrahedron Letters, 34, 3881-3881 (1993)
Tetrahedron Asymmetry, 4, 2427-2427 (1993)
Yan-Hong He et al.
The Journal of organic chemistry, 77(1), 200-207 (2011-11-24)
The direct three-component aza-Diels-Alder reaction of aromatic aldehyde, aromatic amine, and 2-cyclohexen-1-one was catalyzed by hen egg white lysozyme for the first time. Under the optimized conditions investigated in this paper, the enzyme-catalyzed aza-Diels-Alder reaction gave yields up to 98%
M Teresa Barros et al.
Chemical communications (Cambridge, England), 48(88), 10901-10903 (2012-10-02)
An iodine mediated aromatization leading to a one-pot synthesis of iodo-N-arylanilines and N-arylanilines is reported. This highly regioselective aliphatic-aromatic transformation can be performed with various combinations of 2-cyclohexenones and anilines. The presence of a directing group is crucial for achieving
Albert Poater et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 16(48), 14348-14353 (2010-11-18)
The current approach to improve and tune the enantioselective performances of transition-metal catalysts for asymmetric synthesis is mostly focused to modifications of the steric properties of the ancillary ligands of the active metal. Nevertheless, it is also known that electrostatic
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