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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:
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

Signal Word

Warning

Hazard Statements

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


Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

709859-5G:
709859-25G:
709859-BULK:
709859-VAR:


Certificates of Analysis (COA)

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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 (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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