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214000

Sigma-Aldrich

TEMPO

greener alternative

98%

Sinônimo(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

Fórmula empírica (Notação de Hill):
C9H18NO
Número CAS:
2564-83-2
Peso molecular:
156.25
Beilstein:
1422418
Número CE:
219-888-8
Número MDL:
MFCD00009599
Código UNSPSC:
12352119
ID de substância PubChem:
24852819
NACRES:
NA.22

Nível de qualidade

200

Ensaio

98%

forma

solid

adequação da reação

reagent type: oxidant

características do produto alternativo mais ecológico

Catalysis
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

pf

36-38 °C (lit.)

categoria alternativa mais ecológica

Aligned,

temperatura de armazenamento

2-8°C

cadeia de caracteres 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

chave InChI

QYTDEUPAUMOIOP-UHFFFAOYSA-N

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Descrição geral

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.
We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for catalytic efficiency. Find details here.

Aplicação

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

Pictogramas

Corrosion
GHS05

Palavra indicadora

Danger

Frases de perigo

H314,H412

Classificações de perigo

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

Código de classe de armazenamento

8A - Combustible corrosive hazardous materials

Classe de risco de água (WGK)

WGK 2

Ponto de fulgor (°F)

152.6 °F - closed cup

Ponto de fulgor (°C)

67 °C - closed cup

Equipamento de proteção individual

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

Certificados de análise (COA)

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Sigma-Aldrich

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Sigma-Aldrich

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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.
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
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
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