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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)

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Tetrahedron Letters, 34, 3881-3881 (1993)
Tetrahedron Asymmetry, 4, 2427-2427 (1993)
Masaki Okamoto et al.
Chemical communications (Cambridge, England), (47)(47), 7363-7365 (2009-12-22)
Conjugate addition of Et(2)Zn to 2-cyclohexen-1-one catalyzed by Cu(OTf)(2) combined with an azolium salt derived from (S)-leucinol produced the corresponding (S)-adduct, while the use of Cu(acac)(2) in combination with the same ligand afforded the (R)-adduct as a major product.
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
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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