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709859

Sigma-Aldrich

TEMPO on silica gel

Synonym(s):

2,2,6,6-Tetramethyl-1-piperinyloxy, free radical on silica gel, SiliaCAT® TEMPO

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About This Item

MDL number:
MFCD04975412
UNSPSC Code:
12161600
NACRES:
NA.22

form

solid

storage temp.

2-8°C

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General description

FeCl3.6H2O/TEMPO (2,2,6,6-tetramethylpiperidine 1-oxyl radical) in the presence of silica gel has been employed as catalyst for oxidation of alcohols to the corresponding aldehydes and ketones. Doping of stable organic nitroxyl radical TEMPO, over different silica matrices affords reusable highly selective catalysts for various alcohol oxidation reactions. TEMPO-supported on silica gel catalyzed-Anelli oxidation of alcohols has been reported.

Application

Recyclable catalyst in the Anelli oxidation of alcohols.

Legal Information

SiliaCat is a registered trademark of Silicycle, Inc.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCM7303
MKCF8855
MKBS3278V
MKBQ5376V
MKBK3818V

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Selective aerobic oxidation of alcohols catalyzed by iron chloride hexahydrate/TEMPO in the presence of silica gel.
Wang L, et al.
Applied Organometallic Chemistry, 26(1), 37-43 (2012)
T Fey et al.
The Journal of organic chemistry, 66(24), 8154-8159 (2001-11-28)
The application of silica-supported TEMPO as a recyclable catalyst in the Anelli oxidation of alcohols is reported. The catalyst is easily obtained in a one-step reductive amination procedure starting from a commercially available aminopropyl-functionalized silica. Details of the synthesis of
Sol-gel ormosils doped with TEMPO as recyclable catalysts for the selective oxidation of alcohols.
Ciriminna R, et al.
Advanced Synthesis & Catalysis, 344(2), 159-163 (2002)

Articles

TEMPO Catalyzed Oxidations

TEMPO (2,2,6,6-Tetramethylpiperidinyloxy or 2,2,6,6-Tetramethylpiperidine 1-oxyl) and its derivatives are stable nitroxy radicals used as catalysts in organic oxidation reactions. TEMPO was discovered by Lebedev and Kazarnovskii in 1960. The stable free radical nature of TEMPO is due to the presence of bulky substituent groups, which hinder the reaction of the free radical with other molecules.

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