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Phenylarsonic acid

Phenylarsonic acid is the chemical compound with the formula C<sub>6</sub>H<sub>5</sub>AsO(OH)<sub>2</sub>, commonly abbreviated PhAsO<sub>3</sub>H<sub>2</sub>. This colourless solid is an organic derivative of arsenic acid, AsO(OH)<sub>3</sub>, where one OH group has been replaced by a phenyl group. The compound is a buffering agent and a precursor to other organoarsenic compounds, some of which are used in animal nutrition, e.g. 4-hydroxy-3-nitrobenzenearsonic acid.

Preparation and structure

PhAsO<sub>3</sub>H<sub>2</sub> can be prepared in several routes, but a common one entails treatment of phenyl diazonium salts with sodium arsenite (prepared from arsenious acid and base) in the presence of a copper(II) catalyst.

+ NaAsO<sub>3</sub>H<sub>2</sub> → C<sub>6</sub>H<sub>5</sub>AsO<sub>3</sub>H<sub>2</sub> + Na<sup>+</sup> + N<sub>2</sub>

Related derivatives are prepared similarly. It was first prepared by Michaelis and Loenser. X-ray crystallography indicates that the molecules are connected by hydrogen-bonds consistent with short distance of 2.5&nbsp;Å separating the oxygen atoms. The arsenic center is tetrahedral.

Related phenylarsonic acids

Several derivatives of phenylarsonic acid have been used as additives for animal feeds. These include 4-hydroxy-3-nitrobenzenearsonic acid (3-NHPAA, or Roxarsone), p-arsanilic acid (p-ASA), 4-nitrophenylarsonic acid (4-NPAA), and p-ureidophenylarsonic acid (p-UPAA).

References