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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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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)
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
Ozonolysis-reductive amination of olefins.
Pollart KA and Miller RE.
The Journal of Organic Chemistry, 27(7), 2392-2394 (1962)

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