1,1,1-Tris(diphenylphosphinomethyl)ethane

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 C_3v symmetry. It was originally prepared by the reaction of sodium diphenylphosphide and CH₃C(CH₂Cl)₃:^[1]

3 Ph₂PNa + CH₃C(CH₂Cl)₃ → CH₃C[CH₂PPh₂]₃ + 3 NaCl

Quick facts Names, Identifiers ...

1,1,1-Tris(diphenylphosphino­methyl)ethane

Names
Preferred IUPAC name {2-[(Diphenylphosphanyl)methyl]-2-methylpropane-1,3-diyl}bis(diphenylphosphane)
Other names Triphos; tdppme; tdme
Identifiers
CAS Number	22031-12-5 Y[EPA]
3D model (JSmol)	Interactive image
ChemSpider	375165
ECHA InfoCard	100.241.729
EC Number	811-359-5
PubChem CID	423856
CompTox Dashboard (EPA)	DTXSID40329787
InChI InChI=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 Key: BARUNXKDFNLHEV-UHFFFAOYSA-N InChI=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 Key: BARUNXKDFNLHEV-UHFFFAOYAL
SMILES 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
Properties
Chemical formula	C41H39P3
Molar mass	624.67 g/mol
Appearance	white crystals
Melting point	99 to 102 Â°C (210 to 216 Â°F; 372 to 375 K)
Solubility in water	Insoluble
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Safety data sheet (SDS)	Triphos MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 Â°C [77 Â°F], 100 kPa). Infobox references

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It forms complexes with many transition metals, usually as a tripodal ligand.^[2] Such complexes are used to analyze mechanistic aspects of homogeneous catalysts.^[3] 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.^[4]

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.^[5]