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796549

Sigma-Aldrich

Stahl需氧氧化TEMPO溶液

0.2 M in acetonitrile, Solution for Oxidation of Primary Alcohols

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About This Item

UNSPSC代码:
12352000
PubChem化学物质编号:
329768535
NACRES:
NA.22

质量水平

100

表单

liquid

反应适用性

reagent type: oxidant

浓度

0.2 M in acetonitrile

储存温度

2-8°C

SMILES字符串

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

相关类别

一般描述

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

应用

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.

其他说明

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

警示用语：

Danger

危险分类

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

储存分类代码

3 - Flammable liquids

WGK

WGK 3

闪点(°F)

35.6 °F

闪点(°C)

2.0 °C

法规信息

危险化学品

历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
MKCQ2229
MKCP7849
MKCP7836
MKCL2209
MKCF5400

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Practical Aerobic Alcohol Oxidation with Cu/Nitroxyl and Nitroxyl/NOx Catalyst Systems.
Miles KC and Stahl SS.
Aldrichimica Acta, 48(1) (2015)
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)
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

商品

Aerobic Alcohol Oxidation Solutions

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

TEMPO催化氧化

TEMPO（2,2,6,6-四甲基哌啶氧基或2,2,6,6-四甲基哌啶1-氧基）及其衍生物在有机氧化反应催化剂中可以作为稳定的硝酰基使用。TEMPO由Lebedev和Kazarnovskii于1960年发现，其具有的稳定自由基性质得益于其庞大的取代基团阻碍了自由基与其他分子之间发生反应。

相关内容

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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