7056. PBN

Nomenclature

CAS number: 3376-24-7
2-Methyl-N-(phenylmethylene)-2-propanamine N-oxide; benzylidene-tert-butylamine oxide; N-tert-butyl-α-phenylnitrone.
C11H15NO; mol wt 177.24.
C 74.54%, H 8.53%, N 7.90%, O 9.03%.

Description and references

Spin trapping agent for short-lived radicals in biological systems. Prepn: W. D. Emmons, J. Am. Chem. Soc. 79, 5739 (1957); R. W. Murray et al., J. Org. Chem. 61, 8099 (1996). Effects on ischemia in brain: J. W. Phillis, C. Clough-Helfman, Med. Sci. Res. 18, 403 (1990); K. Pahlmark, B. K. Siesj"o, Acta Physiol. Scand. 157, 41 (1996). Review of chemical properties and biological applications: G. Chen et al. in The Oxygen Paradox, PBN and Its Applications in Biology, K. J. A. Davies, F. Ursini, Eds. (Cleup Press, Italy, 1995) pp. 789-800.

Chemical structure

Properties

Crystals, mp 72-74°. Stored at amibient temperature, it is stable for one year unopened. Sensitive to light, especially in solution. Easily sol in medium polar organic solvents such as methanol, ethanol, acetonitrile, toluene, benzene and chloroform. Soly: 2.9% (water); 2.3% (saline); >5% (chloroform). uv max (ethanol): 293.5, 224 nm (ε 17700, 7240); (CH3CN): 298 nm (ε 17716).

Use

Spin trap reagent for carbon- or oxygen- or nitrogen-centered free radicals.