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214000

Sigma-Aldrich

TEMPO

greener alternative

98%

Synonyme(s) :

2,2,6,6-Tetramethylpiperidine 1-oxyl, 2,2,6,6-Tetramethyl-1-piperidinyloxy, free radical, TEMPO

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About This Item

Formule empirique (notation de Hill):
C9H18NO
Numéro CAS:
2564-83-2
Poids moléculaire :
156.25
Numéro Beilstein :
1422418
Numéro CE :
219-888-8
Numéro MDL:
MFCD00009599
Code UNSPSC :
12352119
ID de substance PubChem :
24852819
Nomenclature NACRES :
NA.22

Niveau de qualité

200

Pureté

98%

Forme

solid

Pertinence de la réaction

reagent type: oxidant

Caractéristiques du produit alternatif plus écologique

Catalysis
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sustainability

Greener Alternative Product

Pf

36-38 °C (lit.)

Autre catégorie plus écologique

Aligned,

Température de stockage

2-8°C

Chaîne SMILES 

CC1(C)CCCC(C)(C)N1[O]

InChI

1S/C9H18NO/c1-8(2)6-5-7-9(3,4)10(8)11/h5-7H2,1-4H3

Clé InChI

QYTDEUPAUMOIOP-UHFFFAOYSA-N

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Description générale

TEMPO (2,2,6,6-Tetramethylpiperidin-1-oxyl) is a stable free radical commonly used as an oxidizing agent in organic synthesis. Copper/TEMPO has been utilized in the catalytic oxidation of primary alcohols to aldehydes.
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Application

TEMPO can be used:
  • As a catalytic oxidant for copper-catalyzed, greener oxidation of alcohols under aerobic conditions.
  • As a catalytic oxidant in the iodobenzene diacetae oxidation of nerol to neral.
  • For trapping the styrenyl radical generated from benzoyl peroxide during nitroxide-mediated radical polymerization of styrene.
  • In the carboxylation of water-resistant nanofibrillated cellulose (NFC) films.

Copper(I)/TEMPO-catalyzed aerobic oxidation of primary alcohols to aldehydes with ambient air

Pictogrammes

Corrosion
GHS05

Mention d'avertissement

Danger

Mentions de danger

H314,H412

Classification des risques

Aquatic Chronic 3 - Eye Dam. 1 - Skin Corr. 1C

Code de la classe de stockage

8A - Combustible corrosive hazardous materials

Classe de danger pour l'eau (WGK)

WGK 2

Point d'éclair (°F)

152.6 °F - closed cup

Point d'éclair (°C)

67 °C - closed cup

Équipement de protection individuelle

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Certificats d'analyse (COA)

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Geisslmeir, David; et al.
Monatshefte fur Chemie / Chemical Monthly, 136(9), 1591-1599 (2005)
Wan Ru Leow et al.
Science (New York, N.Y.), 368(6496), 1228-1233 (2020-06-13)
Chemicals manufacturing consumes large amounts of energy and is responsible for a substantial portion of global carbon emissions. Electrochemical systems that produce the desired compounds by using renewable electricity offer a route to lower carbon emissions in the chemicals sector.
Paula Navalpotro et al.
Advanced science (Weinheim, Baden-Wurttemberg, Germany), 5(10), 1800576-1800576 (2018-10-26)
Aqueous biphasic systems (ABS) formed by water, ionic liquids (ILs), and salts, in which the two phases are water rich, are demonstrated here to act as potential membrane-free batteries. This concept is feasible due to the selective enrichment of redox
Jessica M Hoover et al.
Journal of the American Chemical Society, 135(6), 2357-2367 (2013-01-16)
Homogeneous Cu/TEMPO catalyst systems (TEMPO = 2,2,6,6-tetramethylpiperidine-N-oxyl) have emerged as some of the most versatile and practical catalysts for aerobic alcohol oxidation. Recently, we disclosed a (bpy)Cu(I)/TEMPO/NMI catalyst system (NMI = N-methylimidazole) that exhibits fast rates and high selectivities, even
Akira Isogai et al.
Nanoscale, 3(1), 71-85 (2010-10-20)
Native wood celluloses can be converted to individual nanofibers 3-4 nm wide that are at least several microns in length, i.e. with aspect ratios>100, by TEMPO (2,2,6,6-tetramethylpiperidine-1-oxyl radical)-mediated oxidation and successive mild disintegration in water. Preparation methods and fundamental characteristics
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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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