The reaction of geminal bromonitroalkanes with nucleophiles. Part 1. The decomposition of 2-bromo-2-nitropropane-1,3-diol (‘Bronopol’) in aqueous base

Abstract

2-Bromo-2-nitropropane-1,3-diol decomposes in aqueous base to give tris(hydroxymethyl)-nitromethane, glycolic acid, formic acid, methanol and 2,2-dinitroethanol. It also releases NO₂^– and Br^– ions but not BrO^–. These products are shown to form via four concurrent decomposition pathways, three of which involve 2-bromo-2-nitroethanol as a reactive intermediate.