Chemical Properties
white to light yellow crystal powde
Uses
Tri-m-tolylphosphine acts as a reagent for the preparation, crystal structure, multinuclear NMR, antitumor activity, photolysis of silver methylxanthate complexes against human adrenocarcinoma breast cancer cells.
Synthesis
The general procedure for the synthesis of tris(m-tolyl)phosphine from the compound (CAS: 6151-88-8) was as follows: magnesium powder (8 mmol, 4 eq.), trimethylchlorosilane (6 mmol, 3 eq.) and 1,3-dimethyl-2-imidazolidinone (DMI, 8 mL) were mixed and compound 2a (2 mmol) was added. The reaction mixture was stirred at room temperature for 2 hours. Upon completion of the reaction, the reaction was quenched by adding saturated aqueous ammonium carbonate to the mixture and extracted with ether (10 mL × 3). The organic layers were combined, washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was analyzed by 31P NMR, showing a 97:3 ratio of tris(m-tolyl)phosphine (1a) to the feedstock 2a. The crude product was purified by silica gel column chromatography (eluent: hexane/ethyl acetate = 5:1) to give the target product, tris(m-tolyl)phosphine (1a), in 96% yield (Table 1, entry 1).
References
[1] Synthesis, 2011, # 24, p. 4091 - 4098
[2] Tetrahedron Letters, 2015, vol. 56, # 7, p. 918 - 920
[3] Tetrahedron, 2011, vol. 67, # 32, p. 5825 - 5831
