N-Benzylhydroxylamine1

(base)

[622-30-0]  · C7H9NO  · N-Benzylhydroxylamine  · (MW 123.15) (.HCl)

[29601-98-7]  · C7H10ClNO  · N-Benzylhydroxylamine Hydrochloride  · (MW 159.62)

(condenses with a wide variety of aldehydes to afford N-benzylnitrones;2 hydroxylamination reagent for allyl esters under palladium(0) catalysis3)

Physical Data: mp 57 °C; hydrochloride salt, mp 108-110 °C.

Form Supplied in: available commercially as the hydrochloride salt.

Preparative Methods: oxime reduction;4-7 hydroxylamine alkylation;8 isoxazole alkylation.9

Purification: sublimation.

Handling, Storage, and Precautions: hygroscopic. Use in a fume hood.

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


1. For a general review of hydroxylamines see: Roberts, J. S. In Comprehensive Organic Chemistry; Barton, D. H. R.; Ollis, W. D., Eds.; Pergamon: Oxford, 1979; Vol. 2, pp 185-217.
2. Hamer, J.; Macaluso, A. CRV 1964, 64, 473.
3. Murahashi, S.-I.; Imada, Y.; Taniguchi, Y.; Kodera, Y. TL 1988, 29, 2973.
4. Feuer, H.; Vincent, B. F., Jr. JACS 1962, 84, 3771.
5. Feuer, H.; Vincent, B. F., Jr.; Bartlett, R. S. JOC 1965, 30, 2877.
6. Kikugawa, Y.; Kawase, M. CL 1977, 1279.
7. Lund, H. TL 1968, 3651.
8. Isowa, Y.; Kurita, H. BCJ 1974, 47, 720.
9. Doleschall, G. TL 1987, 28, 2993.

Clark H. Cummins

Dow Chemical Company, Midland, MI, USA



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