539430
Cyclohexanone diethyl ketal
97%
Synonym(s):
1,1-Diethoxycyclohexane
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About This Item
Empirical Formula (Hill Notation):
C10H20O2
CAS Number:
Molecular Weight:
172.26
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
EC Number:
216-798-0
MDL number:
Assay:
97%
InChI key
MWUDABUKTZAZCX-UHFFFAOYSA-N
InChI
1S/C10H20O2/c1-3-11-10(12-4-2)8-6-5-7-9-10/h3-9H2,1-2H3
SMILES string
CCOC1(CCCCC1)OCC
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
Quality Level
Related Categories
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.
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Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
3 - Flammable liquids
wgk
WGK 2
flash_point_f
140.0 °F
flash_point_c
60 °C
ppe
Eyeshields, Gloves, type ABEK (EN14387) respirator filter
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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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