trisptolylphosphine

Tris(o-tolyl)phosphine is an organophosphorus compound with the chemical formula P(C6H4CH3)3. It is a tertiary phosphine where the phosphorus atom is bonded to three ortho-tolyl groups. The ortho-tolyl group consists of a phenyl ring with a methyl group attached at the ortho position relative to the point of attachment to the phosphorus. This specific arrangement of substituents around the phosphorus atom influences the compound's electronic and steric properties.

Tris(o-tolyl)phosphine is a white crystalline solid at room temperature. It is soluble in many organic solvents but is generally insoluble in water. Like other triarylphosphines, it is a Lewis base and can act as a ligand in coordination chemistry. The presence of the methyl groups in the ortho positions creates significant steric bulk around the phosphorus atom, which can affect its coordination behavior and reactivity.

This compound finds applications in organic synthesis, particularly as a ligand in transition metal-catalyzed reactions. Its steric and electronic properties can be tuned by the nature of the aryl substituents, making it useful in reactions such as cross-coupling, hydroformylation, and polymerization. The bulky nature of tris(o-tolyl)phosphine can sometimes promote certain reaction pathways or enhance selectivity by influencing the geometry of metal complexes. It is typically synthesized through the reaction of phosphorus trichloride with the appropriate Grignard reagent derived from o-bromotoluene, or via related organometallic couplings.