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02482

Supelco

Cyclohexanone

analytical standard

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About This Item

Linear Formula:
C6H10(=O)
CAS Number:
Molecular Weight:
98.14
Beilstein/REAXYS Number:
385735
EC Number:
MDL number:
UNSPSC Code:
41116107
PubChem Substance ID:
NACRES:
NA.24

grade

analytical standard

Quality Level

vapor density

3.4 (vs air)

vapor pressure

3.4 mmHg ( 20 °C)

assay

≥99.9% (GC)

autoignition temp.

788 °F

shelf life

limited shelf life, expiry date on the label

expl. lim.

1.1 %, 100 °F
9.4 %

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

refractive index

n20/D 1.450 (lit.)
n20/D 1.451

bp

155 °C (lit.)

mp

−47 °C (lit.)

density

0.947 g/mL at 25 °C (lit.)

application(s)

cleaning products
cosmetics
environmental
flavors and fragrances
food and beverages
personal care

format

neat

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 cycloalkanone. It is an industrially important intermediate. It is useful for the preparation of raw materials for various chemical intermediates, such as caprolactam for nylon 6 and adipic acid for nylon 66 synthesis of nylon. It can be synthesized industrially by either the oxidation of cyclohexane or the hydrogenation of phenol.

Application

Cyclohexanone may be used for the following syntheses:
  • vitamin A
  • 2-cyclohexylidene cyclohexanone via Aldol condensation reaction
  • 2-cyclohexenyl cyclohexanone via Aldol condensation reaction
  • bis-(arylmethylidene)cycloalkanones by cross-aldol condensation with aldehydes

signalword

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

3 - Flammable liquids

wgk_germany

WGK 1

flash_point_f

111.2 °F - closed cup

flash_point_c

44 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


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Dodgson I, et al.
Chemistry & Industry, 830 (1989)
Lei Liu et al.
Angewandte Chemie (International ed. in English), 48(12), 2206-2209 (2009-02-10)
On their best behavior: Three zirconium compounds with one-, two-, and three-dimensional structures have been successfully synthesized by the ionothermal approach. The 3D zirconium phosphate (see picture; F green, H white, O red, P pink, Zr yellow) exhibits high catalytic
Xu LX, et al.
Catalysis Communications, 9, 816-816 (2008)
194. A synthesis of vitamin a from cyclohexanone.
Attenburrow J, et al.
Journal of the Chemical Society, 1094-1111 (1952)
Huizhen Liu et al.
Science (New York, N.Y.), 326(5957), 1250-1252 (2009-12-08)
Cyclohexanone is an industrially important intermediate in the synthesis of materials such as nylon, but preparing it efficiently through direct hydrogenation of phenol is hindered by over-reduction to cyclohexanol. Here we report that a previously unappreciated combination of two common

Articles

The aldol condensation reaction is an organic reaction introduced by Charles Wurtz, who first prepared the β-hydroxy aldehyde from acetaldehdye in 1872.

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