Hydroxylaminoxime

Hydroxylaminoxime is an organic compound with the chemical formula HONHCH=NOH. It is a derivative of oxime, where one of the hydrogen atoms of hydroxylamine is replaced by an imine group, or alternatively, it can be viewed as a derivative of formaldehyde oxime where one hydrogen atom on the nitrogen is replaced by a hydroxylamino group. The molecule features both a hydroxylamine moiety and an oxime functional group. It is a white crystalline solid.

This compound can be synthesized through various chemical routes, often involving reactions between hydroxylamine or its derivatives and suitable carbonyl compounds or their precursors. Its chemical reactivity is influenced by the presence of both the hydroxylamino and oxime functional groups, allowing it to participate in a range of reactions, including condensation, oxidation, and reduction.

Hydroxylaminoxime has found applications in analytical chemistry as a reagent for the detection and determination of certain metal ions. Its ability to form stable complexes with specific metals makes it useful in spectrophotometric or gravimetric analysis. It is also explored for its potential in organic synthesis as a building block for more complex molecules due to its bifunctional nature. Safety precautions should be observed when handling hydroxylaminoxime, as with many chemical compounds, and its specific hazards should be consulted from relevant safety data sheets.