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179485

Sigma-Aldrich

4-Oxo-TEMPO

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C9H16NO2
CAS Number:
2896-70-0
Molecular Weight:
170.23
EC Number:
220-778-7
MDL number:
MFCD00006187
UNSPSC Code:
12352000
PubChem Substance ID:
24850816
NACRES:
NA.22

form

solid

storage temp.

2-8°C

SMILES string

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

InChI key

WSGDRFHJFJRSFY-UHFFFAOYSA-N

General description

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

Pictograms

Environment
GHS09

Signal Word

Warning

Hazard Statements

H400

Precautionary Statements

P273

Hazard Classifications

Aquatic Acute 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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)
R Konaka et al.
Redox report : communications in free radical research, 6(5), 319-325 (2002-01-10)
We previously reported that irradiation of titanium dioxide (TiO2) in ethanol generates both singlet oxygen (1O2) and superoxide anion (O2*-) as measured by EPR spectroscopy. The present study describes the production of reactive oxygen species upon irradiation of TiO2 in
Jingyao Zhang et al.
Shock (Augusta, Ga.), 52(1), 92-101 (2018-07-22)
The aim of the present study was to investigate the effect of cold atmospheric discharge plasma-activated saline (DPAS) on abdominal sepsis. For in vitro research, Methicillin-resistant Staphylococcus aureus (MRSA) was treated with DPAS, and the survival was detected. For in
Marina Bennati et al.
Physical chemistry chemical physics : PCCP, 12(22), 5902-5910 (2010-05-12)
Water (1)H relaxation rate measurements of (15)N-(2)H-TEMPONE solutions at temperatures ranging from 298 to 328 K have been performed as a function of magnetic field from 0.00023 to 9.4 T, corresponding to (1)H Larmor frequencies of 0.01 to 400 MHz.
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