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IUPAC name
Other names
tempol; tanol; TMPN; 4-Oxypiperidol; nitroxyl 2; HyTEMPO
2226-96-2 YesY
ChEMBL ChEMBL607023 YesY
ChemSpider 121639 YesY
Jmol-3D images Image
PubChem 137994
Molar mass 172.24 g/mol
Appearance orange crystals
Melting point 71–73 °C (160–163 °F; 344–346 K)[1]
GHS pictograms GHS-pictogram-exclam.svg[2]
GHS signal word Warning[2]
H302, H315, H319, H335[2]
P261, P305+351+338[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

4-Hydroxy-TEMPO or TEMPOL, formally 4-hydroxy-2,2,6,6-tetramethylpiperidin-1-oxyl, is a heterocyclic compound. Like the related TEMPO, it is used as a catalyst and chemical oxidant by virtue of being a stable radical. It's major appeal over TEMPO is that is significantly cheaper, being produced from triacetone amine, which it itself made via the condensation of acetone and ammonia. This makes it economically viable on an industrial scale. [3]

In medicine, it is recognized as an agent for detoxifying reactive oxygen species. It catalyses the disproportionation of superoxide.[4]


  1. ^ Zakrzewski, Jerzy; Krawczyk, Maria (1 January 2011). "Reactions of Nitroxides. Part XII [1]. – 2,2,6,6-Tetramethyl-1-oxyl- 4-piperidyl Chloroformate – A New Reactive Nitroxyl Radical. A One-pot Synthesis of 2,2,6,6-Tetramethyl-1-oxyl-4-piperidyl N,N-Dialkyl-carbamates". Zeitschrift für Naturforschung B 66 (5). doi:10.1515/znb-2011-0509. 
  2. ^ a b c d Sigma-Aldrich Co., 4-Hydroxy-TEMPO. Retrieved on 2015-08-24.
  3. ^ Ciriminna, Rosaria; Pagliaro, Mario (15 January 2010). "Industrial Oxidations with Organocatalyst TEMPO and Its Derivatives". Organic Process Research & Development 14 (1): 245–251. doi:10.1021/op900059x. 
  4. ^ Wilcox, C. S.; Pearlman, A. (2008). "Chemistry and Antihypertensive Effects of Tempol and Other Nitroxides". Pharmacological Reviews 60 (4): 418–69. doi:10.1124/pr.108.000240. PMC 2739999. PMID 19112152. 

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