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Merck
CN

29255

2-Cyclohexen-1-one

purum, ≥95.0% (GC)

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About This Item

Linear Formula:
C6H8(=O)
CAS Number:
930-68-7
Molecular Weight:
96.13
EC Number:
213-223-5
UNSPSC Code:
12352100
PubChem Substance ID:
24857595
Beilstein/REAXYS Number:
1280477
MDL number:
MFCD00001577

Key Documents

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vapor pressure

760 mmHg ( 168 °C)

grade

purum

assay

≥95.0% (GC)

refractive index

n20/D 1.488 (lit.), n20/D 1.489

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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General description

Aza-Baylis-Hillman reaction of N-sulfonated imines with 2-cyclohexen-1-one in the presence of (R)-2′-dimethylphosphanyl-[1,1′]binaphthalenyl-2-ol (chiral phosphine Lewis base) has been investigated. The asymmetric conjugate addition of medium order alkyl cuprate reagents to 2-cyclohexen-1-one with the help of phosphorus ligand has been reported. Morita-Baylis-Hillman reaction of 2-cyclohexen-1-one with a wide range of aromatic aldehydes catalyzed by bis(thio)urea organocatalysts and DABCO (1,4-diazabicyclo[2.2.2]octane) has been reported.

Application

2-Cyclohexen-1-one has been employed as a catalyst in decarboxylation of α-amino acids to the corresponding amino compounds.

Disclaimer

may discolor to brown on storage

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

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

Regulatory Information

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Amino Acid Decarboxylation Catalyzed by 2-Cyclohexen-1-One.
Hashimoto M, et al.
Chemistry Letters (Jpn), 893, 896-896 (1986)
Min Shi et al.
Organic letters, 10(6), 1043-1046 (2008-02-21)
Novel bis(thio)urea organocatalysts were synthesized from axially chiral (R)-(-)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl-2,2'-diamine (H8-BINAM), and their catalytic abilities have been examined in the Morita-Baylis-Hillman reaction of 2-cyclohexen-1-one or 2-cyclopenten-1-one with a wide range of aromatic aldehydes in combination with DABCO. The best result was
Catalytic, asymmetric aza-Baylis-Hillman reaction of< i> N</i>-sulfonated imines with 2-cyclohexen-1-one and 2-cyclopenten-1-one in the presence of a chiral phosphine Lewis base.
Shi M and Chao-QunL.
Tetrahedron Asymmetry, 16(7), 1385-1391 (2005)
Chiral phosphorus ligands for the asymmetric conjugate addition of organocopper reagents.
Alexakis A, et al.
Tetrahedron Asymmetry, 4(12), 2427-2430 (1993)
Ronaldo Mariz et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 16(48), 14335-14347 (2010-11-16)
A family of chiral C(2)-symmetric disulfoxide ligands possessing biaryl atropisomeric backbones has been synthesized by using the Andersen methodology. Complete characterization includes X-ray crystallographic studies of all ligands and some of their rhodium complexes. Their synthesis, optical purity, electronic properties
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