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458597

Sigma-Aldrich

Cyclohexanone dimethyl ketal

99%

Synonym(s):

1,1-Dimethoxycyclohexane

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About This Item

Linear Formula:
C6H10(OCH3)2
CAS Number:
933-40-4
Molecular Weight:
144.21
MDL number:
MFCD00043714
UNSPSC Code:
12352100
PubChem Substance ID:
24869484
NACRES:
NA.22

assay

99%

refractive index

n20/D 1.439 (lit.)

bp

83 °C/50 mmHg (lit.)

density

0.948 g/mL at 25 °C (lit.)

SMILES string

COC1(CCCCC1)OC

InChI

1S/C8H16O2/c1-9-8(10-2)6-4-3-5-7-8/h3-7H2,1-2H3

InChI key

XPIJMQVLTXAGME-UHFFFAOYSA-N

General description

Cyclohexanone dimethyl ketal reacts with trimethylsilane in the presence of trimethylsilyl triflate to form the corresponding ether. It can also undergo allylation and propargylation in the presence of indium to form the corresponding homoallylic or homopropargylic alcohol, respectively.

pictograms

Flame
GHS02

signalword

Warning

hcodes

H226

Hazard Classifications

Flam. Liq. 3

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

111.2 °F - closed cup

flash_point_c

44 °C - closed cup

ppe

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Trimethysilyl triflate in organic synthesis
Noyori R, et al.
Tetrahedron, 37(23, 3899-3910 (1981)
Sebastian Krickl et al.
Physical chemistry chemical physics : PCCP, 19(35), 23773-23780 (2017-07-01)
In this contribution, we (i) link the mesoscopic structuring of the binary structured solvent mixture H
Preparation of ketone acetals from linear ketones and alcohols.
Lorette NB, et al.
The Journal of Organic Chemistry, 24(11), 1731-1733 (1959)
Indium mediated allylation and propargylation reactions of dimethyl acetals and ketals.
Kwon JS, et al.
Tetrahedron Letters, 42(10), 1957-1959 (2001)
M Ogata et al.
Journal of medicinal chemistry, 30(6), 1054-1068 (1987-06-01)
To find orally active antifungal agents, novel imidazolyl- and 1,2,4-triazolylpropanolones I and related compounds II-IV were synthesized. Compounds I were derived from ketones V (method A), alpha-diketone IX (method B), alpha-hydroxy ketones X (method C), alpha-chloro ketone XII (method D)

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