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426369

Sigma-Aldrich

TEMPO

purified by sublimation, 99%

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:
24866699
NACRES:
NA.22

Ensaio

99%

Formulário

solid

purificado por

sublimation

adequação da reação

reagent type: oxidant

pf

36-38 °C (lit.)

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

For a synthetic protocol using NMP initiators, contributed by Prof. Karen Wooley, please visit our technology spotlight.

Aplicação

Stable nitroxide radical useful in controlling living polymerizations
TEMPO (2,2,6,6-Tetramethyl-1-piperidinyloxy) was used for trapping the styrenyl radical generated from benzoyl peroxide during nitroxide-mediated radical polymerization of styrene. TEMPO-mediated oxidation was employed for the carboxylation of water-resistant nanofibrillated cellulose (NFC) films.

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

Escolha uma das versões mais recentes:

Certificados de análise (COA)

Lot/Batch Number
MKCB0475V
MKBJ7394V
MKBW0278V
MKBR7572V
MKBW6930V

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MitoTEMPO ≥98% (HPLC)

Sigma-Aldrich

SML0737

MitoTEMPO

4-Acetamido-2,2,6,6-tetramethylpiperidine 1-oxyl purum, ≥98.0% (HPLC)

Sigma-Aldrich

00375

4-Acetamido-2,2,6,6-tetramethylpiperidine 1-oxyl

4-Oxo-TEMPO-d16, free radical for ESR-spectroscopy, 97 atom % D

Sigma-Aldrich

485268

4-Oxo-TEMPO-d16, free radical

Block copolymer synthesis using a commercially available nitroxide-mediated radical polymerization (NMP) initiator.
Lee NS and Wooley KL.
Material Matters, 5, 8-15 (2010)
Hayaka Fukuzumi et al.
Carbohydrate polymers, 93(1), 172-177 (2013-03-08)
Various mechanical disintegration conditions in water were applied to 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO)-oxidized cellulose to prepare TEMPO-oxidized cellulose nanofibrils (TOCNs) of uniform widths ∼4 nm but with three different average lengths, 200, 680, and 1100 nm. The viscosity average degrees of polymerization
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
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
Xiaolong Liu et al.
The Journal of organic chemistry, 78(17), 8531-8536 (2013-08-16)
Imidazolium salts bearing TEMPO groups react with commercially available copper powder affording Cu-NHC complexes. The in situ generated Cu-NHC-TEMPO complexes are quite efficient catalysts for aerobic oxidation of primary alcohols into aldehydes. The catalyst is easily available, and various primary
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TEMPO Catalyzed Oxidations

TEMPO (2,2,6,6-Tetramethylpiperidinyloxy or 2,2,6,6-Tetramethylpiperidine 1-oxyl) and its derivatives are stable nitroxy radicals used as catalysts in organic oxidation reactions. TEMPO was discovered by Lebedev and Kazarnovskii in 1960. The stable free radical nature of TEMPO is due to the presence of bulky substituent groups, which hinder the reaction of the free radical with other molecules.

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