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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:
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)

Quality Level

200

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

Signal Word

Danger

Hazard Statements

H226,H301,H310 + H330

Hazard Classifications

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

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

132.8 °F - closed cup

Flash Point(C)

56 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCK4273
BCCH9410
BCCJ5125
BCCG2924
BCCC6086

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Tetrahedron Letters, 34, 3881-3881 (1993)
Tetrahedron Asymmetry, 4, 2427-2427 (1993)
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
Tatsushi Imahori et al.
Organic letters, 14(4), 1172-1175 (2012-02-03)
An efficient approach to prepare para-aryl phenols has been developed by using a Pd-catalyzed tandem γ-arylation/aromatization of 2-cyclohexen-1-one derivatives with aryl bromides. This approach provides various p-aryl phenols from the phenol surrogates, 2-cyclohexen-1-one derivatives, in a single reaction step on
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