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C102180

Sigma-Aldrich

Cyclohexanone

ReagentPlus®, 99.8%

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Synonym(s):
pimelic ketone
Linear Formula:
C6H10(=O)
CAS Number:
Molecular Weight:
98.14
Beilstein:
385735
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.21

vapor density

3.4 (vs air)

Quality Level

vapor pressure

3.4 mmHg ( 20 °C)

product line

ReagentPlus®

Assay

99.8%

form

liquid

autoignition temp.

788 °F

expl. lim.

1.1 %, 100 °F
9.4 %

refractive index

n20/D 1.450 (lit.)

pH

~7 (20 °C, 70 g/L)

bp

155 °C (lit.)

mp

−47 °C (lit.)

density

0.947 g/mL at 25 °C (lit.)

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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1 of 4

This Item
W3909091.02888ARK2189
Cyclohexanone ReagentPlus®, 99.8%

Sigma-Aldrich

C102180

Cyclohexanone

Cyclohexanone 99.8%

Sigma-Aldrich

W390909

Cyclohexanone

Cyclohexanone EMPLURA®

Supelco

1.02888

Cyclohexanone

Cyclohexanone

SAFC

ARK2189

Cyclohexanone

vapor pressure

3.4 mmHg ( 20 °C)

vapor pressure

3.4 mmHg ( 20 °C)

vapor pressure

4.5 hPa ( 20 °C)

vapor pressure

3.4 mmHg ( 20 °C)

assay

99.8%

assay

99.8%

assay

≥99% (GC)

assay

-

form

liquid

form

liquid

form

liquid

form

-

autoignition temp.

788 °F

autoignition temp.

788 °F

autoignition temp.

430 °C

autoignition temp.

788 °F

expl. lim.

1.1 %, 100 °F, 9.4 %

expl. lim.

1.1 %, 100 °F, 9.4 %

expl. lim.

1.1 % (v/v)

expl. lim.

1.1 %, 100 °F, 9.4 %

General description

Cyclohexanone is a cyclic ketone that can be prepared by either the oxidation of cyclohexane or the hydrogenation of phenol. It is an important raw material in the production of caprolactam, adipic acid, and nylon. It is also used as a solvent in insecticides, wood stains, paint and varnish removers, spot removers, cellulosics, and natural and synthetic resins and lacquers.

Application

Cyclohexanone can be used as a reactant to synthesize:
  • Secondary amines by reductive amination.
  • Adipic acid.
  • Tetrasubstituted propargylamines.
It can also be used as a solvent in the triphenylmethyl chloride-initiated atom transfer radical polymerization of styrene to prepare polystyrene in the presence of a catalyst.

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

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

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

111.2 °F - closed cup

Flash Point(C)

44 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Selective transfer hydrogenation of phenol to cyclohexanone on supported palladium catalyst using potassium formate as hydrogen source under open atmosphere.
Patil RD and Sasson Y.
Applied Catalysis A: General, 499, 227-231 (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)
Synthesis, characterization, and application of silica supported ionic liquid as catalyst for reductive amination of cyclohexanone with formic acid and triethyl amine as hydrogen source.
Tamboli AH, et al.
Chinese Journal of Catalysis, 36 (2015)
Green and Sustainable Heterogeneous Organo-Catalyst for Asymmetric Aldol Reactions.
Sadiq M, et al.
Modern Research in Catalysis, 4(2), 43-43 (2015)
Synthesis of tetrasubstituted propargylamines from cyclohexanone by solvent-free copper (II) catalysis.
Palchak ZL, et al.
Green Chemistry, 17(3), 1802-1810 (2015)

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