acetylphosphine

Acetylphosphine, also known as acylphosphine, is an organophosphorus compound with the formula C2H5OP (commonly written CH3COPH2). It consists of a phosphorus atom bonded to an acetyl group via the carbonyl carbon, giving the acylphosphine motif R-CO-PH2 with R = CH3. It is the simplest member of the acylphosphine family and is of interest mainly in fundamental studies of P–C(O) bonding and reactivity.

Acetylphosphine is highly reactive and sensitive to air and moisture, and it is not typically handled as a bulk material. It is usually prepared and consumed in situ in specialized laboratories under inert atmosphere. It tends to undergo rapid oxidation and polymerization, and its storage requires stringent exclusion of air and moisture.

Synthesis routes reported in the literature are described for small-scale, research contexts and often involve conversion of acetylated phosphorus precursors or reduction of corresponding acyl phosphoranes; specifics depend on the procedures described in particular studies. In chemical reactions, acetylphosphine serves as a reactive acylphosphine source for the formation of P–C bonds and as an intermediate in the preparation of more complex organophosphorus compounds. Its use is largely limited to academic research due to its instability and handling challenges.

See also: Acylphosphine, Phosphine, Organophosphorus compound.