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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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25 ML
¥21,900

¥21,900

Estimated to ship onJune 13, 2025From市川市大町368

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25 ML
¥21,900

About This Item

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

¥21,900

Estimated to ship onJune 13, 2025From市川市大町368

Request a Bulk Order

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

Related Categories

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

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

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.

PDSCL

Deleterious substance

FSL

Group 4: Flammable liquids
Type 1 petroleums
Hazardous rank II
Water soluble liquid

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

796549-VAR:
796549-BULK:
796549-25ML:4548173907710

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Certificates of Analysis (COA)

Lot/Batch Number
MKCQ2229
MKCP7849
MKCP7836
MKCL2209
MKCF5400

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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

Articles

Aerobic Alcohol Oxidation Solutions

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

Related Content

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.

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