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179485

Sigma-Aldrich

4-Oxo-TEMPO

Synonyme(s) :

4-Oxo-2,2,6,6-tetramethyl-1-piperidinyloxy, free radical

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About This Item

Formule empirique (notation de Hill):
C9H16NO2
Numéro CAS:
2896-70-0
Poids moléculaire :
170.23
Numéro CE :
220-778-7
Numéro MDL:
MFCD00006187
Code UNSPSC :
12352000
ID de substance PubChem :
24850816
Nomenclature NACRES :
NA.22

Forme

solid

Niveau de qualité

100

Groupe fonctionnel

ketone

Température de stockage

2-8°C

Chaîne SMILES 

CC1(C)CC(=O)CC(C)(C)N1[O]

InChI

1S/C9H16NO2/c1-8(2)5-7(11)6-9(3,4)10(8)12/h5-6H2,1-4H3

Clé InChI

WSGDRFHJFJRSFY-UHFFFAOYSA-N

Description générale

4-Oxo-TEMPO is formed by the reaction of 2,2,6,6-tetramethyl-4-piperidone (4-oxo-TMP) and 1O2. It is a stable paramagnetic product formed during the irradiation of TiO2 in aqueous suspensions.

Application

4-Oxo-TEMPO was employed as nitroxide standard to investigate the generation of singlet oxygen by photoexcited TiO2 in ethanol by ESR spectroscopy. It may be employed as free radical polarizing agent in dynamic nuclear polarization (DNP) studies.
Free-radical nitroxide spin probe typically used for:
  • Redox sources for anodes in lithium secondary batteries
  • Free-radical biological studies
  • Radical spin-trapping
  • Electron paramagnetic resonance studies
  • Polymer chemisty and synthesis applications

Pictogrammes

Environment
GHS09

Mention d'avertissement

Warning

Mentions de danger

H400

Conseils de prudence

P273

Classification des risques

Aquatic Acute 1

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

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Certificats d'analyse (COA)

Lot/Batch Number
STBH8026
STBC4019V
S71093V
S71093
07415JJ

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

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Fuminori Hyodo et al.
Journal of magnetic resonance (San Diego, Calif. : 1997), 197(2), 181-185 (2009-01-23)
Nitroxides, unlike trityl radicals, have shorter T(2)s which until now were not detectable in vivo by a time-domain pulsed Electron Paramagnetic Resonance (EPR) spectrometer at 300 MHz since their phase memory times were shorter than the spectrometer recovery times. In
Mark Tseitlin et al.
Journal of magnetic resonance (San Diego, Calif. : 1997), 208(2), 279-283 (2010-12-18)
In rapid scan EPR the magnetic field is scanned through the signal in a time that is short relative to electron spin relaxation times. Previously it was shown that the slow-scan lineshape could be recovered from triangular rapid scans by
Maria-Teresa Türke et al.
Physical chemistry chemical physics : PCCP, 12(22), 5893-5901 (2010-05-11)
Dynamic nuclear polarization is emerging as a potential tool to increase the sensitivity of NMR aiming at the detection of macromolecules in liquid solution. One possibility for such an experimental design is to perform the polarization step between electrons and
Paul L Wood et al.
Brain research, 1095(1), 190-199 (2006-05-30)
The concept of "oxidative stress" has become a mainstay in the field of neurodegeneration but has failed to differentiate critical events from epiphenomena and sequalae. Furthermore, the translation of current concepts of neurodegenerative mechanisms into effective therapeutics for neurodegenerative diseases
Impact of Gd3+ on DNP of [1-13C] pyruvate doped with trityl OX063, BDPA, or 4-oxo-TEMPO.
Lumata L, et al.
The Journal of Physical Chemistry A, 116(21), 5129-5138 (2012)
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Articles

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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