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It has been suggested that this article be split into multiple articles accessible from a disambiguation page. (September 2010) Triphos IUPAC name Bis(diphenylphosphinoethyl)phenylphosphine Other names Triphos, Identifiers CAS number 23582-02-7 Properties Molecular formula C34H29P3 Molar mass 534.55 g/mol Appearance white crystals Melting point 129-130 °C Solubility in water Insoluble  Y(what is this?)  (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references Triphos IUPAC name 1,1,1-Tris(diphenylphosphinomethyl)ethane Other names Triphos, tdppme, tdme Identifiers CAS number 22031-12-5 Properties Molecular formula C41H39P3 Molar mass 624.67 g/mol Appearance white crystals Melting point 99-102 °C Solubility in water Insoluble Hazards S-phrases 22-24/25 Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references Triphos is the name for two organophosphorus compounds. Both are air sensitive white solids that serve as tridentate ligands in coordination and organometallic chemistry. One is C3-symmetric and the other has Cs symmetry. Contents 1 Bis(diphenylphosphinoethyl)phenylphosphine 1.1 Synthesis 1.2 Coordination chemistry 2 1,1,1-Tris(diphenylphosphinomethyl)ethane 2.1 Synthesis 2.2 Coordination chemistry 3 References Bis(diphenylphosphinoethyl)phenylphosphine Bis(diphenylphosphinoethyl)phenylphosphine is called triphos, is a linear tridentate triphosphine. Synthesis Bis(diphenylphosphinoethyl)phenylphosphine is prepared by the free-radical-catalysed addition of phenylphosphine to vinyldiphenylphosphine:[1] 2 Ph2PCH=CH2 + H2PPh → [Ph2PCH2CH2]2PPh Coordination chemistry This isomer of triphos is more flexible and can bind to an octahedral metal center give either a facial or meridional isomers. Many of its derivatives are square planar complexes of the type [MX(triphos)]+ (M = Ni, Pd, Pt; X = halide). 1,1,1-Tris(diphenylphosphinomethyl)ethane 1,1,1-Tris(diphenylphosphinomethyl)ethane is called triphos. Synthesis Triphos is prepared by the reaction of sodium diphenylphosphide and CH3C(CH2Cl)3:[2] 3 Ph2PNa + CH3C(CH2Cl)3 → CH3C[CH2PPh2]3 + 3 NaCl The required sodium diphenylphosphide is conveniently obtained by cleaving triphenylphosphine with sodium in liquid ammonia. Coordination chemistry Triphos forms complexes with many transition metals. It usually functions as a tripodal ligand that occupies three adjacent coordination sites.[3] Triphos complexes often exhibit high thermal stability. Such complexes are used to analyze mechanistic aspects of homogenous catalysts.[4] 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.[5] Triphos sometimes behaves as a bidentate-chelating ligand. Illustrative cases include fac-[Mn(CO)3Br(η2-triphos)] and [M(CO)4(η2-triphos)],where M is Cr, Mo, or W. [3] Triphos serves as a tridentate-bridging ligand in an icosohedral 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. [6] References ^ "Synthesis of Polytertiary Phosphines and ‘Mixed’ Phosphorus–Sulphur and ‘Mixed’ Phosphorus–Nitrogen Polydentate Ligands via Free-Radical Catalysis" Daniel L. DuBois, William H. Myers and Devon W. Meek J. Chem. Soc., Dalton Trans., 1975, 1011-1015.doi:10.1039/DT9750001011 ^ W. Hewertson and H. R. Watson (1962). "283. The preparation of di- and tri-tertiary phosphines". J. Chem. Soc.: 1490–1494. doi:10.1039/JR9620001490.  ^ a b Fernández, Eduardo J.; Gimeno, M. Concepción; Laguna, Antonio; Laguna, Mariano; López-de-Luzuriaga, José M.; & Olmos, Elena (1996). "Different Coordination modes of 1,1,1-tris(diphenylphosphinomethyl) ethane Ligand in Gold(I) and Gold(III) Complexes". Journal of Organometallic Chemistry 514: 169. doi:10.1016/0022-328X(95)06025-R.  ^ 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. doi:10.1021/om9602264.  ^ 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}Re(CO)2]". Organometallics 9: 226. doi:10.1021/om00115a035.  ^ Cooper, Mervyn K.; Henrick, Kim; McPartlin, Mary; & Latten, Jozef L. (1982). "The synthesis and X-ray structure of trichloro-1,1,1-(diphenylphosphinomethyl)ethanetrigold(I)". Inorganica Chimica Acta 65 (2): L185. doi:10.1016/S0020-1693(00)93540-0.