Saltar al contenido
Merck
Todas las fotos(1)

Key Documents

View All Documentation

796549

Sigma-Aldrich

Stahl Aerobic Oxidation TEMPO solution

0.2 M in acetonitrile, Solution for Oxidation of Primary Alcohols

Iniciar sesiónpara Ver la Fijación de precios por contrato y de la organización
Todas las fotos(1)

About This Item

UNSPSC Code:
12352000
PubChem Substance ID:
329768535
NACRES:
NA.22

Quality Level

100

form

liquid

reaction suitability

reagent type: oxidant

concentration

0.2 M in acetonitrile

storage temp.

2-8°C

SMILES string

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

InChI key

BQFURWVGIDXRNB-UHFFFAOYSA-N

General description

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.

Other Notes

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

related product

Referencia del producto
Descripción
Precios

signalword

Danger

Hazard Classifications

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

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

35.6 °F

flash_point_c

2.0 °C

Elija entre una de las versiones más recientes:

Certificados de análisis (COA)

Lot/Batch Number
MKCQ2229
MKCP7849
MKCP7836
MKCL2209
MKCF5400

¿No ve la versión correcta?

Si necesita una versión concreta, puede buscar un certificado específico por el número de lote.

Busque por un COA

¿Ya tiene este producto?

Encuentre la documentación para los productos que ha comprado recientemente en la Biblioteca de documentos.

Visite la Librería de documentos

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
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
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

Artículos

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.

Contenido relacionado

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.

Nuestro equipo de científicos tiene experiencia en todas las áreas de investigación: Ciencias de la vida, Ciencia de los materiales, Síntesis química, Cromatografía, Analítica y muchas otras.

Póngase en contacto con el Servicio técnico