1,1,1-Tris(diphenylphosphinomethyl)ethane

Triphos.svg 1,1,1-Tris(diphenylphosphinomethyl)ethane {2-[(Diphenylphosphanyl)methyl]-2-methylpropane-1,3-diyl}bis(diphenylphosphane) Triphos; tdppme; tdme 22031-12-5 correct EPA 811-359-5 423856 375165 CC(CP(C1=CC=CC=C1)C2=CC=CC=C2)(CP(C3=CC=CC=C3)C4=CC=CC=C4)CP(C5=CC=CC=C5)C6=CC=CC=C6 1/C41H39P3/c1-41(32-42(35-20-8-2-9-21-35)36-22-10-3-11-23-36,33-43(37-24-12-4-13-25-37)38-26-14-5-15-27-38)34-44(39-28-16-6-17-29-39)40-30-18-7-19-31-40/h2-31H,32-34H2,1H3 BARUNXKDFNLHEV-UHFFFAOYAL 1S/C41H39P3/c1-41(32-42(35-20-8-2-9-21-35)36-22-10-3-11-23-36,33-43(37-24-12-4-13-25-37)38-26-14-5-15-27-38)34-44(39-28-16-6-17-29-39)40-30-18-7-19-31-40/h2-31H,32-34H2,1H3 BARUNXKDFNLHEV-UHFFFAOYSA-N C41H39P3 624.67 g/mol white crystals Insoluble 99 to 102 Triphos MSDS 07 Warning 315 319 335 261 264 271 280 302+352 304+340 305+351+338 312 321 332+313 337+313 362 403+233 405 501 1,1,1-Tris(diphenylphosphinomethyl)ethane, also called Triphos, is an organophosphorus compound with the formula CH3C[CH2PPh2]3. An air-sensitive white solid, it is a tripodal ligand ("three-legged") of idealized C3v symmetry. It was originally prepared by the reaction of sodium diphenylphosphide and CH3C(CH2Cl)3: J. Chem. Soc. 1962 1490–1494 10.1039/JR9620001490 283. The preparation of di- and tri-tertiary phosphines W. Hewertson H. R. Watson amp 3 Ph2PNa + CH3C(CH2Cl)3 → CH3C[CH2PPh2]3 + 3 NaCl It forms complexes with many transition metals, usually as a tripodal ligand.Phosphorus Tripodal Ligands Huttner, G. Strittmatter, J. Sandhoefner, S. Comprehensive Coordination Chemistry II 2004 1 297–322 10.1016/B0-08-043748-6/01082-3 9780080437484 Such complexes are used to analyze mechanistic aspects of homogeneous catalysts.Bianchini, Claudio Marchi, Andrea Marvelli, Lorenza Peruzzini, Maurizio Romerosa, Antonio Rossi, Roberto 1996 Multiple Re-C Bonds at the [{MeC(CH2PPh2)3}Re(CO)2]+ Auxiliary Organometallics 15 3804 10.1021/om9602264 For example, rhodium forms complexes with CH3C[CH2PPh2]3 like [(triphos)RhCl(C2H4)], [(triphos)RhH(C2H4)], and [(triphos)Rh(C2H5)(C2H4)], provide model intermediates in the catalytic cycle for hydrogenation of alkenes.Bianchini, Claudio Meli, Andrea Peruzzini, Maurizio Vizza, Francesco 1990 Tripodal Polyphosphine Ligands in Homogeneous Catalysis. 1. Hydrogenation and Hydroformylation of Alkynes and Alkenes Assisted by Organorhodium Complexes with MeC(CH2PPh2)3 Organometallics 9 226–240 10.1021/om00115a035 Triphos sometimes behaves as a bidentate ligand. Illustrative cases include fac-[Mn(CO)3Br(η2-triphos)] and [M(CO)4(η2-triphos)], where M is Cr, Mo, or W. Triphos serves as a tridentate-bridging ligand in an icosahedral Au13 cluster. The phosphine bridges three chlorogold(I) groups to form the tripod molecule of trichloro-1,1,1-(diphenylphosphinomethyl)ethanetrigold(I), CH3C[CH2PPh2AuCl]3.Cooper, Mervyn K. Henrick, Kim McPartlin, Mary Latten, Jozef L. amp 1982 The synthesis and X-ray structure of trichloro-1,1,1-(diphenylphosphinomethyl)ethanetrigold(I) Inorganica Chimica Acta 65 L185 10.1016/S0020-1693(00)93540-0 2 Related ligands Tris(aminomethyl)ethane, a tripodal triamine (CH3C(CH2NH2)3) Bis(diphenylphosphinoethyl)phenylphosphine (PhP(C2H4PPh2)2) Tris(2-diphenylphosphinoethyl)amine N[CH2CH2PPh2]10.1021/ja01022a020 Low- and high-spin five-coordinate cobalt(II) and nickel(II) complexes with tris(2-diphenylphosphinoethyl)amine 1968 Sacconi L. Bertini I. Journal of the American Chemical Society 90 20 5443–5446 References Category:Tertiary phosphines Category:Phenyl compounds Category:Chelating agents Category:Tridentate ligands