Abstract
[17508-17-7] C6H5N3O5 (MW 199.14) InChI = 1S/C6H5N3O5/c7-14-6-2-1-4(8(10)11)3-5(6)9(12)13/h1-3H,7H2 InChIKey = YLACRFYIUQZNIV-UHFFFAOYSA-N (widely applicable electrophilic amination reagent; converts aldoximes to cyanides and benzofurans) Alternate Names: DNPHA; NH2ODNP. Physical Data: pale yellow needles, mp 112–113 °C. A rapid active-site-directed inhibitor of D-amino acid oxidase.1 Preparative Methods: can be generated economically from the reaction of 2,4-dinitrochlorobenzene and ethyl N-hydroxyacetimidate with subsequent hydrolysis.2 t-Butyl N-hydroxycarbamate3 and N-hydroxy-5-norbornene-2,3-dicarboximide4 can be used in place of ethyl N-hydroxyacetimidate. Handling, Storage, and Precautions: an otherwise stable, crystalline solid, DNPHA has been known to detonate when combined with Potassium Hydride and therefore direct combination of these two reagents should be avoided.5 2,4-Dinitrophenol, a byproduct of amination reactions involving DNPHA, is a highly toxic, flammable solid. Use in a fume hood.
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