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Merck
CN

02482

Cyclohexanone

analytical standard

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About This Item

Linear Formula:
C6H10(=O)
CAS Number:
108-94-1
Molecular Weight:
98.14
UNSPSC Code:
41116107
NACRES:
NA.24
PubChem Substance ID:
329747444
EC Number:
203-631-1
Beilstein/REAXYS Number:
385735
MDL number:
MFCD00001625

Key Documents

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Product Name

Cyclohexanone, analytical standard

InChI key

JHIVVAPYMSGYDF-UHFFFAOYSA-N

InChI

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

SMILES string

O=C1CCCCC1

grade

analytical standard

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

Quality Level

100

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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

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.

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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

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

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
BCCL8588
BCCH4976
BCCB7763
BCBT3526
BCBQ7521V

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Dodgson I, et al.
Chemistry & Industry, 830 (1989)
Xu LX, et al.
Catalysis Communications, 9, 816-816 (2008)
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
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
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Articles

Aldol Condensation Reaction

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

羟醛缩合反应

羟醛缩合反应是由Charles Wurtz推出的有机反应，他于1872年首次从乙醛中制备了β-羟基醛。

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