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539430

Sigma-Aldrich

Cyclohexanone diethyl ketal

97%

Synonym(s):

1,1-Diethoxycyclohexane

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About This Item

Empirical Formula (Hill Notation):
C10H20O2
CAS Number:
1670-47-9
Molecular Weight:
172.26
EC Number:
216-798-0
MDL number:
MFCD00037723
UNSPSC Code:
12352100
PubChem Substance ID:
24878399
NACRES:
NA.22

Assay

97%

refractive index

n20/D 1.4360 (lit.)

bp

76-78 °C/20 mmHg (lit.)

density

0.908 g/mL at 25 °C (lit.)

functional group

ether
ketal

SMILES string

CCOC1(CCCCC1)OCC

InChI

1S/C10H20O2/c1-3-11-10(12-4-2)8-6-5-7-9-10/h3-9H2,1-2H3

InChI key

MWUDABUKTZAZCX-UHFFFAOYSA-N

General description

Cyclohexanone diethyl ketal (1,1-Diethoxycyclohexane) reacts with 1,3,2-benzodioxaborole [catecholborane (CB)] to form the corresponding ether. It undergoes thermal elimination reaction in gas-phase to yield 1-ethoxycyclohexene and ethanol.

Application

Cyclohexanone diethyl ketal may be used in the preparation of 1-ethoxycyclohexene.

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Warning

Hazard Statements

H226,H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 2

Flash Point(F)

140.0 °F

Flash Point(C)

60 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCG4125
MKCG0505
MKBH5860V
05705DC

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Felix Rosas et al.
The journal of physical chemistry. A, 116(2), 846-854 (2011-12-22)
The gas-phase thermal elimination of 2,2-diethoxypropane was found to give ethanol, acetone, and ethylene, while 1,1-diethoxycyclohexane yielded 1-ethoxycyclohexene and ethanol. The kinetics determinations were carried out, with the reaction vessels deactivated with allyl bromide, and the presence of the free
Reactions of Enol Ethers with Carbenes. V. Rearrangements of Dihalocyclopropanes Derived from Six-, Seven-, and Eight-Membered Cyclic Enol Ethers1.
Parham WE, et al.
Journal of the American Chemical Society, 87(2), 321-328 (1965)
Catecholborane (1, 3, 2-benzodioxaborole). A versatile reducing agent.
Kabalka GW, et al.
The Journal of Organic Chemistry, 42(3), 512-517 (1977)
Ozonolysis-reductive amination of olefins.
Pollart KA and Miller RE.
The Journal of Organic Chemistry, 27(7), 2392-2394 (1962)

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