4-Hydroxy-TEMPO

4-Hydroxy-TEMPO
Names
	IUPAC name 1-λ1-oxidanyl-2,2,6,6-tetramethylpiperidin-4-ol
	Other names tempol; tanol; TMPN; 4-Oxypiperidol; nitroxyl 2; HyTEMPO
Identifiers
CAS Number	2226-96-2 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL607023 ;
ChemSpider	121639 ;
ECHA InfoCard	100.017.056
PubChem CID	137994;
CompTox Dashboard (EPA)	DTXSID4041280 ;
	InChI InChI=1S/C9H18NO2/c1-8(2)5-7(11)6-9(3,4)10(8)12/h7,11H,5-6H2,1-4H3 Key: UZFMOKQJFYMBGY-UHFFFAOYSA-N ; InChI=1S/C9H18NO2/c1-8(2)5-7(11)6-9(3,4)10(8)12/h7,11H,5-6H2,1-4H3 Key: UZFMOKQJFYMBGY-UHFFFAOYSA-N;
	SMILES CC1(C)CC(O)CC(C)(C)N1[O];
Properties
Chemical formula	C9H18NO2
Molar mass	172.248 g·mol−1
Appearance	Orange crystals
Melting point	71–73 °C (160–163 °F; 344–346 K)
Hazards
	GHS labelling:
Pictograms	class="wikitable collapsible" style="min-width: 50em;"

See also

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Signal word

| Warning^[3]

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Hazard statements

| H302, H315, H319, H335^[3]

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Precautionary statements

| P261, P305+P351+P338^[3]

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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

verify (what is ^YN ?)

Infobox references

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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. Its major appeal over TEMPO is that is less expensive, being produced from triacetone amine, which is itself made via the condensation of acetone and ammonia. This makes it economically viable on an industrial scale.^[4]

In biochemical research, it has been investigated as an agent for limiting reactive oxygen species. It catalyzes the disproportionation of superoxide, facilitates hydrogen peroxide metabolism, and inhibits Fenton chemistry.^[5] It is often present as a structural element in hindered amine light stabilizers, which are commonly used stabilizers in plastics.

References

^ 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.
^ "Globally Harmonized System of Classification and Labelling of Chemicals" (pdf). 2021. Annex 3: Codification of Statements and Pictograms (pp 268–385).
^ ^a ^b ^c ^d Sigma-Aldrich Co., 4-Hydroxy-TEMPO. Retrieved on 2015-08-24.
^ 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.
^ 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.

[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.

[GHS2021_annex-3-2] "Globally Harmonized System of Classification and Labelling of Chemicals" (pdf). 2021. Annex 3: Codification of Statements and Pictograms (pp 268–385).

[sigma-3] Sigma-Aldrich Co., 4-Hydroxy-TEMPO. Retrieved on 2015-08-24.

[4] 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.

[5] 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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Names


IUPAC name 1-λ¹-oxidanyl-2,2,6,6-tetramethylpiperidin-4-ol
Other names tempol; tanol; TMPN; 4-Oxypiperidol; nitroxyl 2; HyTEMPO
Identifiers
CAS Number	2226-96-2^Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL607023^Y
ChemSpider	121639^Y
ECHA InfoCard	100.017.056
PubChem CID	137994
CompTox Dashboard (EPA)	DTXSID4041280
InChI InChI=1S/C9H18NO2/c1-8(2)5-7(11)6-9(3,4)10(8)12/h7,11H,5-6H2,1-4H3^Y Key: UZFMOKQJFYMBGY-UHFFFAOYSA-N^Y InChI=1S/C9H18NO2/c1-8(2)5-7(11)6-9(3,4)10(8)12/h7,11H,5-6H2,1-4H3 Key: UZFMOKQJFYMBGY-UHFFFAOYSA-N
SMILES CC1(C)CC(O)CC(C)(C)N1[O]
Properties
Chemical formula	C₉H₁₈NO₂
Molar mass	172.248 g·mol⁻¹
Appearance	Orange crystals
Melting point	71–73 °C (160–163 °F; 344–346 K)^[1]
Hazards
GHS labelling:
Pictograms	class="wikitable collapsible" style="min-width: 50em;"
Pictogram	Code	Symbol description	Image link
	GHS01	{{GHS exploding bomb}}	Image:GHS-pictogram-explos.svg	Explosive
	GHS02	{{GHS flame}}	Image:GHS-pictogram-flamme.svg
	GHS03	{{GHS flame over circle}}	Image:GHS-pictogram-rondflam.svg
	GHS04	{{GHS gas cylinder}}	Image:GHS-pictogram-bottle.svg
	GHS05	{{GHS corrosion}}	Image:GHS-pictogram-acid.svg	Corrosive
	GHS06	{{GHS skull and crossbones}}	Image:GHS-pictogram-skull.svg	Accute Toxic
	GHS07	{{GHS exclamation mark}}	Image:GHS-pictogram-exclam.svg	Irritant
	GHS08	{{GHS health hazard}}	Image:GHS-pictogram-silhouette.svg	Health Hazard
	GHS09	{{GHS environment}}	Image:GHS-pictogram-pollu.svg	Environment