TEMPOL
Title: TEMPOL
CAS Registry Number: 2226-96-2
CAS Name: 4-Hydroxy-2,2,6,6-tetramethyl-1-piperidinyloxy
Additional Names: 4-hydroxy-TEMPO; 4-hydroxy-2,2,6,6-tetramethyl piperidine N-oxide; 4-hydroxy-2,2,6,6-tetramethylpiperidinooxy
Molecular Formula: C9H18NO2
Molecular Weight: 172.24
Percent Composition: C 62.76%, H 10.53%, N 8.13%, O 18.58%
Literature References: Stable nitroxyl radical; water-soluble analogue of TEMPO, q.v. Functions as a membrane-permeable radical scavenger. Prepn: E. G. Rozantsev, Bull. Acad. Sci. USSR Div. Chem. Sci. 12, 2085 (1964). Energy transfer studies: N. N. Quan, A. V. Guzzo, J. Phys. Chem. 85, 140 (1981). IR conformation study: W. A. Bueno, L. Degrève, J. Mol. Struct. 74, 291 (1981). Solid state NMR spectra: C. J. Groombridge, M. J. Perkins, J. Chem. Soc. Chem. Commun. 1991, 1164. LC/MS/MS determn: I. D. Podmore, J. Chem. Res. Synop. 2002, 574. Use as a phase transfer catalyst: X.-Y. Wang et al., Synth. Commun. 29, 157 (1999). Review of effects in animal models for shock, ischemia-reperfusion injury, and inflammation: C. Thiemermann, Crit. Care Med. 31, S76-S84 (2003).
Properties: Crystals from ether + hexane, mp 71.5°. uv max (hexane): 240, 450-500 (e ~1800, ~5). uv max (ethanol): 242, 435-455 (e ~3800, ~10). Sol in water.
Melting point: mp 71.5°
Absorption maximum: uv max (hexane): 240, 450-500 (e ~1800, ~5); uv max (ethanol): 242, 435-455 (e ~3800, ~10)
Use: Spin label for EPR studies; phase transfer dehydration catalyst; antioxidant; inhibitor of olefin free radical polymerization.

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