154917-36-9Relevant articles and documents
Mechanism of the polarographic reduction of 5-bromo-5-nitro-1,3-dioxane (Bronidox)
Rath,Hoffmann
, p. 443 - 448 (2007/10/03)
The electrochemical behavior at the dropping mercury electrode (DME) of 5-bromo-5-nitro-1,3-dioxane (BND), a preservative used in cosmetic preparations, was investigated. BND is reduced in 5 waves. The first wave (E(1/2)=+0.2 V) corresponds to the cleavage of bromide, giving 5-nitro-1,3- dioxane-anion (NDA). The second wave (E(1/2)= -0.2 V) is caused by adsorption. NDA is protonated, giving 5-nitro-1,3-dioxane (ND) which is reduced at E(1/2) = -0.6 V. In parallel to the electrochemical reduction ND is also formed by the chemical reaction of BND with metallic mercury. The reduction of the remaining adsorbed NDA at the DME is responsible for the fourth wave (E(1/2) = -1.1 V). Both ND and NDA are reduced to 1,3-dioxa-5- cyclohexylhydroxylamine (DCH). Finally DCH is reduced to 1,3-dioxa-5- cyclohexylamine (DCA). The reduction products were isolated, identified and a reduction mechanism is proposed.