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179485

Sigma-Aldrich

4-Oxo-TEMPO

Sinonimo/i:

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

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About This Item

Formula empirica (notazione di Hill):
C9H16NO2
Numero CAS:
2896-70-0
Peso molecolare:
170.23
Numero CE:
220-778-7
Numero MDL:
MFCD00006187
Codice UNSPSC:
12352000
ID PubChem:
24850816
NACRES:
NA.22

Stato

solid

Gruppo funzionale

ketone

Temperatura di conservazione

2-8°C

Stringa SMILE

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
WSGDRFHJFJRSFY-UHFFFAOYSA-N

Descrizione generale

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.

Applicazioni

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

Pittogrammi

Environment
GHS09

Avvertenze

Warning

Indicazioni di pericolo

H400

Consigli di prudenza

P273

Classi di pericolo

Aquatic Acute 1

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)

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Certificati d'analisi (COA)

Lot/Batch Number
STBH8026
STBC4019V
S71093V
S71093
07415JJ

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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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Articoli

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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