Skip to Content
Merck
All Photos(1)

Documents

796549

Sigma-Aldrich

Stahl Aerobic Oxidation TEMPO solution

0.2 M in acetonitrile, Solution for Oxidation of Primary Alcohols

Sign Into View Organizational & Contract Pricing


About This Item

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

Quality Level

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.

Signal Word

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 Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

35.6 °F

Flash Point(C)

2.0 °C


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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service