Skip to Content
Merck
All Photos(1)

Documents

405752

Sigma-Aldrich

2-Allylcyclohexanone

97%

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Linear Formula:
H2C=CHCH2C6H9(=O)
CAS Number:
94-66-6
Molecular Weight:
138.21
EC Number:
202-352-2
MDL number:
MFCD00043548
UNSPSC Code:
12352100
PubChem Substance ID:
24865329
NACRES:
NA.22

Assay

97%

form

liquid

refractive index

n20/D 1.469 (lit.)

bp

94 °C/23 mmHg (lit.)

density

0.927 g/mL at 25 °C (lit.)

SMILES string

C=CCC1CCCCC1=O

InChI

1S/C9H14O/c1-2-5-8-6-3-4-7-9(8)10/h2,8H,1,3-7H2

InChI key

UPGHEUSRLZSXAE-UHFFFAOYSA-N

Related Categories

General description

2-Allylcyclohexanone is a β,γ-unsaturated ketone. Selective oxidation of 2-allylcyclohexanone by benzonitrile-hydrogen peroxide has been reported. Asymmetric synthesis of 2-alkylcyclohexanones by alkylation of cyclohexanone enamines (III) of L-proline ester derivatives has been described. Oxidation of 2-allylcyclohexanone by 90% hydrogen peroxide catalyzed by arsonated polystyrene has been studied.

Application

2-Allylcyclohexanone may be used in the synthesis of the following:
  • bicyclo[3.3.1]non-2-en-9-one
  • R-(-)-epilachnene, an antipode of the defensive droplets from the Mexican bean beetle, Epilachna varivestis

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Stereochemical Studies. IX. Asymmetric Synthesis of 2-Alkylcyclo-hexanones with Enamine Alkylation.
Hiroi K, et al.
Chemical & Pharmaceutical Bulletin, 20, 246-257 (1972)
Bridget McCarthy Cole et al.
The Journal of organic chemistry, 61(22), 7832-7847 (1996-11-01)
Mn(III)-based oxidative free-radical cyclization of unsaturated ketones is a versatile synthetic procedure with broad applicability. For example, oxidation of cyclopentanone 1a with 2 equiv of Mn(OAc)(3).2H(2)O and 1 equiv of Cu(OAc)(2).H(2)O in AcOH at 80 degrees C for 1.5 h
Biphase and triphase catalysis. Arsonated polystyrenes as catalysts in the Baeyer-Villiger oxidation of ketones by aqueous hydrogen peroxide.
Jacobson SE, et al.
Journal of the American Chemical Society, 101(23), 6938-6946 (1979)
A Modified Thermodynamically Controlled Deracemization of 2-Allylcyclohexanone and Its Application to Asymmetric Synthesis of (R)-(-)-Epilachnene.
Kaku H, et al.
Chemistry Letters (Jpn), 33(5), 516-517 (2004)
A simplified procedure for epoxidation by benzonitrile-hydrogen peroxide. Selective oxidation of 2-allylcyclohexanone.
Payne GB.
Tetrahedron, 18(6), 763-765 (1962)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service