Tris(3-sulfophenyl)phosphine Trisodium Salt (Triphenylphosphine-3,3',3''-trisulfonic acid trisodium salt) is a reagent used in organic synthesis such as benzothiazole-based cycloplatinated chromophores.
Triphenylphosphine-3,3',3''-trisulfonic acid trisodium salt (TPPTS) is synthesized by sulfonation of triphenylphosphine with oleum (i.e., concentrated H2SO4 and SO3). Various parameters (triphenylphosphine/oleum ratio,wt % of SO3, time, temperature, and agitation speed) have been studied and modified to suppress the formation of by-products such as phosphines with a low degree of sulfonation and phosphine oxides. One particularly attractive method employs orthoboric acid B(OH)3, concentrated H2SO4, and a controlled SO3 concentration and cleanly affords either disulfonated ligand (TPPDS) or TPPTS with negligible oxidation and no by-products.
Triphenylphosphine-3,3',3''-trisulfonic acid trisodium salt (TPPTS) can be used as a capping agent in the synthesis of TPPTS stabilized palladium nanoparticles (PdNPs) using K2PdCl4 as the palladium source and HCOONa as the reductant. The TPPTS stabilized PdNPs are applicable as an efficient catalyst in the aqueous phase Suzuki-Miyaura coupling reaction at room temperature. TPPTS is also a ligand in the metal-catalyzed hydroformylation of functionalized olefins and direct arylation polymerization reactions.
Solid Triphenylphosphine-3,3',3''-trisulfonic acid trisodium salt (TPPTS) is substantially stable to air, but bottles of TPPTS should be flushed with N2 or Ar and kept tightly closed for prolonged storage. TPPTS is slowly oxidized to the phosphine oxide in the solution. Therefore, oxygen-free solvents are preferred.
