N-t-Butylhydroxylamine1

t-BuNHOH

[16649-50-6]  · C4H11NO  · N-t-Butylhydroxylamine  · (MW 89.14) (.HCl)

[57497-39-9]  · C4H12ClNO  · N-t-Butylhydroxylamine Hydrochloride  · (MW 125.60)

(condenses with a wide variety of aldehydes to afford N-t-butylnitrones;2 condenses with alkynes to afford N-t-butylnitrones;3 used with phenylacetyl chloride in the synthesis of aziridinones;4 alkene amination5)

Physical Data: mp 64-65 °C; hydrochloride, mp 183-185 °C.

Form Supplied in: available commercially as the hydrochloride salt.

Preparative Methods: nitro reduction;6 oxaziridine hydrolysis;7-9 amine oxidation.10

Purification: recrystallization from pentane.

Handling, Storage, and Precautions: hygroscopic; oxidizes slowly to the nitroso compound.

For a discussion of this reagent, see the entry for N-Cyclohexylhydroxylamine.


1. For a general review of hydroxylamines see: Roberts, J. S. In Comprehensive Organic Chemistry; Barton, D. H. R.; Ollis, W. D., Ed.; Pergamon: Oxford, 1979; Vol. 2, pp 185-217.
2. Hamer, J.; Macaluso, A. CRV 1964, 64, 473.
3. Aurich, H. G.; Hahn, K. CB 1979, 112, 2769.
4. Bladon, C. M.; Kirby, G. W. CC 1982, 1402.
5. Liebeskind, L. S.; Sharpless, K. B.; Wilson, R. D.; Ibers, J. A. JACS 1978, 100, 7061.
6. Calder, A.; Forrester, A. R.; Hepburn, S. P. OS 1972, 52, 77; OSC 1988, 6, 803.
7. Emmons, W. D. JACS 1957, 79, 5739.
8. Schalenbach, R.; Waldmann, H.; Ingendoh, A. Ger. Patent 3 535 451, 1987 (CA 1987, 107, 77 305p).
9. Aue, D. H.; Thomas, D. JOC 1974, 39, 3855.
10. Holman, R. J.; Perkins, M. J. JCS(C) 1970, 2195.

Clark H. Cummins

Dow Chemical Company, Midland, MI, USA



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