Organophosphinic acid

An organophosphinic acid is an organophosphorus compound with the formula R_2−nH_nPO₂H (R = alkyl, aryl). One or both P-H bonds in the parent hypophosphorous acid (aka phosphinic acid) are replaced by organic groups. The Cyanex family of dialkylphosphinic acids are used in hydrometallurgy to extract metals from ores.

Monalkylphosphinic acids have the formula OP(OH)(H)R, with the simplest example being methylphosphinic acid.

Phosphinic acid adds to Michael acceptors, for example with acrylamide it gives H(HO)P(O)CH₂CH₂C(O)NH₂.

Dialkylphosphinic acids have the formula R₂PO₂H, where R is an alkyl or aryl group. The phosphorus(V) center has tetrahedral molecular geometry. Under the brand names Aerophine and Cyanex, dialkylphosphinic acids are used in extraction and separation of metals as one of the techniques of hydrometallurgy^[1] Characteristically the organic substituents are branched to confer solubility and preclude crystallization.^[2]

Formaldehyde and H₃PO₂ react to give (HOCH₂)₂PO₂H.

The dithiodialkyphosphinic acids (R₂PS₂H) are related to the diorganodithiophosphates with the formula (RO)₂PS₂H, which are also used as complexing agents in the purification of metals. The phosphates are more prone to hydrolysis owing to the greater lability of the RO-P linkage vs the direct C-P bond.

• Phosphinate, salts of H₂PO₂⁻