trisotolylphosphine

Trisotolylphosphine, also known as tris(3-methylphenyl)phosphine or tris(m-tolyl)phosphine, is an organophosphorus compound with the chemical formula (CH3C6H4)3P. It is a tertiary phosphine where the phosphorus atom is bonded to three tolyl groups, specifically the meta-tolyl isomer. This compound typically appears as a white solid.

The synthesis of trisotolylphosphine can be achieved through various methods, often involving the reaction of a Grignard reagent derived from m-bromotoluene with phosphorus trichloride. Alternatively, organolithium reagents can be employed.

Trisotolylphosphine finds application as a ligand in organometallic chemistry and homogeneous catalysis. Its steric and electronic properties, influenced by the tolyl substituents, make it suitable for stabilizing metal complexes and promoting specific catalytic transformations. Like other phosphine ligands, it can coordinate to transition metals, altering their reactivity and selectivity in reactions such as cross-coupling, hydrogenation, and hydroformylation. The presence of the methyl groups on the aromatic rings can influence the solubility and steric bulk of the resulting metal complexes. Due to its tertiary phosphine nature, it is susceptible to oxidation, forming the corresponding phosphine oxide.