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176141 Sigma-Aldrich

4-Hydroxy-TEMPO

97%

Synonym: 4-Hydroxy-2,2,6,6-tetramethylpiperidine 1-oxyl, TEMPOL

  • CAS Number 2226-96-2

  • Empirical Formula (Hill Notation) C9H18NO2

  • Molecular Weight 172.24

  •  Beilstein/REAXYS Number 1422990

  •  EC Number 218-760-9

  •  MDL number MFCD00006478

  •  PubChem Substance ID 24850555

  •  NACRES NA.22

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Properties

Related Categories Analytical Reagents, Analytical/Chromatography, Chemical Synthesis, Electron Spin Resonance (ESR/EPR) Spectroscopy, Radical Chemistry,
Quality Level   200
assay   97%
composition   Carbon content, 60.6-65.0%
  Nitrogen content, 7.8-8.4%
mp   69-71 °C (lit.)
storage temp.   2-8°C
SMILES string   CC1(C)CC(O)CC(C)(C)N1[O]
InChI   1S/C9H18NO2/c1-8(2)5-7(11)6-9(3,4)10(8)12/h7,11H,5-6H2,1-4H3
InChI key   UZFMOKQJFYMBGY-UHFFFAOYSA-N

Description

General description

4-Hydroxy-TEMPO is a 4-substituted 2,2,6,6-tetramethylpiperidyl-1-oxy (TEMPO) derivative. It is a low-molecular weight compound and has been proposed as superoxide dismutase mimic.

Application

4-Hydroxy-TEMPO (HO-TEMPO) may be employed as catalyst for the oxidation of alcohols to the corresponding aldehydes. It may be employed for the preparation of TEMPO based polymer catalyst systems, which are useful for the Anelli oxidation of various primary alcohols. It may be used as starting reagent in the synthesis of 4-(2,2,6,6-tetramethyl-1-oxyl-4-piperidoxyl)butyl bromide.

A fluorous-tagged TEMPO derivative was prepared from the derived TEMPO propargylic ether and subsequent "click" reaction with a fluorous azide. This TEMPO derivative proved to be a highly effective catalyst in the oxidation of alcohols with bleach.

Spin label for studying biological compounds and polymers.

Spin label reagent used in the chatacterization of antagonist and agonist binding sites of NK1 receptor. Also used to measure reactive oxygen generation in heart muscle by electron spin resonance spectroscopy. Cells that overexpress CYP2E1 can be protected from arachidonic acid toxicity damage by TEMPOL.

Packaging

1, 5, 25 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Target organs 
Respiratory system
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 1
RTECS 
TN8991000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

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 discovere...
Keywords: Aerobic, Capillary electrophoresis, Catalysis, Chromatography, Coupling reactions, Oxidations, Polymerization reactions, Size-exclusion chromatography, Solvents

Peer-Reviewed Papers
15

References

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