Synlett 2014; 25(08): 1186-1187
DOI: 10.1055/s-0033-1341110
© Georg Thieme Verlag Stuttgart · New York


Zhanhui Yang
State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, Faculty of Science, Beijing University of Chemical Technology, Beijing 100029, P. R. of China   Email:
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Publication History

Publication Date:
03 April 2014 (online)


O-(2,4-Dinitrophenyl)hydroxylamine (1) is an orange solid (mp = 112 °C)[1] and fairly stable when exposed to air. It is commercially available and can be readily synthesized by Charette’s method on a large scale:[1] Nucleophilic aromatic substitution of 2,4-dinitrochlorobenzene by N-hydroxyphthalimide followed by hydrazinolysis gives 1 in 94% yield over two steps (Scheme [1]).

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Scheme 1

As an electrophilic amination reagent, 1 is used to donate a free NH2 group to a variety of C-, N-, and O-nucleophiles to give products of significant importance in both synthetic and medicinal chemistry. The byproduct is 2,4-dinitrophenol (Scheme [2]). Amination with 1 features the advantages of mild reaction conditions, simple and safe operations, and wide substrate scope.

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Scheme 2
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