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796549

Sigma-Aldrich

Stahl Aerobic Oxidation TEMPO solution

0.2 M in acetonitrile, Solution for Oxidation of Primary Alcohols

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About This Item

Code UNSPSC :
12352000
ID de substance PubChem :
329768535
Nomenclature NACRES :
NA.22

Forme

liquid

Pertinence de la réaction

reagent type: oxidant

Concentration

0.2 M in acetonitrile

Température de stockage

2-8°C

Chaîne SMILES 

CN1C=CN=C1.CC2(C)CCCC(C)(C)N2[O].C3(C4=NC=CC=C4)=NC=CC=C3

InChI

1S/C10H8N2.C9H18NO.C4H6N2/c1-3-7-11-9(5-1)10-6-2-4-8-12-10;1-8(2)6-5-7-9(3,4)10(8)11;1-6-3-2-5-4-6/h1-8H;5-7H2,1-4H3;2-4H,1H3

Clé InChI

BQFURWVGIDXRNB-UHFFFAOYSA-N

Description générale

Stahl Aerobic Oxidation TEMPO solution contains 1-methylimidazole (NMI), 2,2′-bipyridyl (bpy), and TEMPO. It is widely employed for the oxidation of alcohols.

Application

This convenience solution can be used in tandem with tetrakisacetonitrile copper(I) triflate (685038) for the oxidation of primary alcohols through aerobic conditions developed by the Stahl Research Group.

Autres remarques

Technology Spotlight:
Aerobic Alcohol Oxidation Solutions

Stable TEMPO and ABNO Catalyst Solutions for User-Friendly (bpy)Cu/Nitroxyl- Catalyzed Aerobic Alcohol Oxidation

Practical Aerobic Alcohol Oxidation with Cu/Nitroxyl and Nitroxyl/NOx Catalyst Systems

Produit(s) apparenté(s)

Réf. du produit
Description
Tarif

Mention d'avertissement

Danger

Classification des risques

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Liq. 2 - Repr. 2 - Skin Corr. 1C

Code de la classe de stockage

3 - Flammable liquids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

35.6 °F

Point d'éclair (°C)

2.0 °C

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Consulter la Bibliothèque de documents

Continuous-Flow Aerobic Oxidation of Primary Alcohols with a Copper(I)/TEMPO Catalyst
Greene, JF, et al.
Organic Process Research & Development, 17 (10), 1247?1251-1247?1251 (2013)
Practical Aerobic Alcohol Oxidation with Cu/Nitroxyl and Nitroxyl/NOx Catalyst Systems.
Miles KC and Stahl SS.
Aldrichimica Acta, 48(1) (2015)
Jessica M Hoover et al.
Journal of the American Chemical Society, 133(42), 16901-16910 (2011-08-25)
Aerobic oxidation reactions have been the focus of considerable attention, but their use in mainstream organic chemistry has been constrained by limitations in their synthetic scope and by practical factors, such as the use of pure O(2) as the oxidant
Janelle E Steves et al.
The Journal of organic chemistry, 80(21), 11184-11188 (2015-10-13)
Two solutions, one consisting of bpy/TEMPO/NMI and the other bpy/ABNO/NMI (bpy =2,2'-bipyridyl; TEMPO = 2,2,6,6-tetramethylpiperidine N-oxyl, ABNO = 9-azabicyclo[3.3.1]nonane N-oxyl; NMI = N-methylimidazole), in acetonitrile are shown to have good long-term stability (≥1 year) under air at 5 °C. The
Jessica M Hoover et al.
Nature protocols, 7(6), 1161-1166 (2012-05-29)
This protocol describes a practical laboratory-scale method for aerobic oxidation of primary alcohols to aldehydes, using a chemoselective Cu(I)/TEMPO (TEMPO = 2,2,6,6-tetramethyl-1-piperidinyloxyl) catalyst system. The catalyst is prepared in situ from commercially available reagents, and the reactions are performed in

Articles

Aerobic Alcohol Oxidation Solutions

Alcohol oxidation yields aldehydes and ketones, crucial intermediates in organic synthesis.

Aerobic Alcohol Oxidation Solutions

Alcohol oxidation yields aldehydes and ketones, crucial intermediates in organic synthesis.

Aerobic Alcohol Oxidation Solutions

Alcohol oxidation yields aldehydes and ketones, crucial intermediates in organic synthesis.

Aerobic Alcohol Oxidation Solutions

Alcohol oxidation yields aldehydes and ketones, crucial intermediates in organic synthesis.

Contenu apparenté

Stahl Group – Professor Product Portal

he Stahl Lab focuses on the development of catalysts and catalytic reactions for selective oxidation of organic molecules, with particular emphasis on aerobic oxidation reactions.

Notre équipe de scientifiques dispose d'une expérience dans tous les secteurs de la recherche, notamment en sciences de la vie, science des matériaux, synthèse chimique, chromatographie, analyse et dans de nombreux autres domaines..

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