75-17-2

FORMOXIME is used for formylation of arenes via diazonium salts; 1,3-dipolar cycloaddition with electron-deficient alkenes and alkynes to form isoxazolidines.

FORMOXIME is synthesized by reactioning of 37% aqueous formaldehyde with hydroxylamine hydrochloride to which sodium hydroxide in 30% aqueous methanol is added (eq 1).3-5 This procedure affords useful solutions of formaldoxime in aqueous methanol.3 Alternatively, paraformaldehyde with hydroxylamine hydrochloride in the presence of sodium acetate in aqueous medium produces a 10% solution of formaldoxime.

Formoxime is stable as hydrochloride; the oxime readily polymerizes at room temperature and is more stable in aqueous solution. Handle in a fume hood.