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^Y
ChEMBL	ChEMBL607023^Y
ChemSpider	121639^Y
Jmol interactive 3D	Image
PubChem	137994
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	172.24 g/mol
Appearance	orange crystals
Melting point	71–73 °C (160–163 °F; 344–346 K)^[1]
Hazards
GHS pictograms	^[2]
GHS signal word	Warning^[2]
GHS hazard statements	H302, H315, H319, H335^[2]
GHS precautionary statements	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).
Y verify (what is ^YN ?)
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 is 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, facilitates hydrogen peroxide metabolism, and inhibit Fenton chemistry.^[4]

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.
1 2 3 4 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.

External links

TEMPO

TEMPOL

This article is issued from Wikipedia - version of the Monday, March 21, 2016. The text is available under the Creative Commons Attribution/Share Alike but additional terms may apply for the media files.