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29140

Sigma-Aldrich

Cyclohexanone

puriss. p.a., ≥99.5% (GC)

Synonym(s):

pimelic ketone

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About This Item

Linear Formula:
C6H10(=O)
CAS Number:
Molecular Weight:
98.14
Beilstein:
385735
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.21

vapor density

3.4 (vs air)

Quality Level

vapor pressure

3.4 mmHg ( 20 °C)

grade

puriss. p.a.

Assay

≥99.5% (GC)

autoignition temp.

788 °F

expl. lim.

1.1 %, 100 °F
9.4 %

impurities

≤0.5% water

evapn. residue

≤0.05%

refractive index

n20/D 1.450 (lit.)
n20/D 1.450

bp

155 °C (lit.)

mp

−47 °C (lit.)

density

0.947 g/mL at 25 °C (lit.)

cation traces

Al: ≤0.5 mg/kg
Ba: ≤0.1 mg/kg
Bi: ≤0.1 mg/kg
Ca: ≤0.5 mg/kg
Cd: ≤0.05 mg/kg
Co: ≤0.02 mg/kg
Cr: ≤0.02 mg/kg
Cu: ≤0.02 mg/kg
Fe: ≤0.1 mg/kg
K: ≤0.5 mg/kg
Li: ≤0.1 mg/kg
Mg: ≤0.1 mg/kg
Mn: ≤0.02 mg/kg
Mo: ≤0.1 mg/kg
Na: ≤0.5 mg/kg
Ni: ≤0.02 mg/kg
Pb: ≤0.1 mg/kg
Sr: ≤0.1 mg/kg
Zn: ≤0.1 mg/kg

SMILES string

O=C1CCCCC1

InChI

1S/C6H10O/c7-6-4-2-1-3-5-6/h1-5H2

InChI key

JHIVVAPYMSGYDF-UHFFFAOYSA-N

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General description

Cyclohexanone is a cyclic ketone mainly used as an intermediate in the synthesis of nylon.

Application

Cyclohexanone may undergo asymmetric Michael addition with aryl and alkyl nitroolefins in the presence of pyrrolidine-urea based catalysts to form the corresponding adducts. It may also be used in the synthesis of a wide range of compounds such as adipic acid, 2-(hydroxy(phenyl)methyl)cyclohexanone, 2-allylcyclohexan-1-one, tetrasubstituted propargylamines and N-cyclohexyl-benzyl amine derivatives.

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 1

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

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(S)-(-)-2-allylcyclohexanone
Braun M, et al
Organic Syntheses, 86, 47-47 (2009)
Pyrrolidine- thiourea as a bifunctional organocatalyst: highly enantioselective Michael addition of cyclohexanone to nitroolefins
Cao CL, et al
Organic Letters, 8(14), 2901-2904 (2006)
Green and Sustainable Heterogeneous Organo-Catalyst for Asymmetric Aldol Reactions.
Sadiq M, et al.
Modern Research in Catalysis, 4(2), 43-43 (2015)
First Order Hyperpolarizabilities, NPA and Fukui Functions of Cyclohexanone by Density Functional Theory Method.
Gangadharan RP and Krishnan SS.
Acta Physica Polonica A, 127(3), 748-752 (2015)
194. A synthesis of vitamin a from cyclohexanone.
Attenburrow J, et al.
Journal of the Chemical Society, 1094-1111 (1952)

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