Triphos

Triphos

Names
IUPAC name Bis(diphenylphosphinoethyl)phenylphosphine
Other names Triphos
Identifiers
CAS Number	23582-02-7 Y
3D model (JSmol)	Interactive image
ChemSpider	81424 N
PubChem CID	90192
InChI InChI=1S/C34H33P3/c1-6-16-30(17-7-1)35(26-28-36(31-18-8-2-9-19-31)32-20-10-3-11-21-32)27-29-37(33-22-12-4-13-23-33)34-24-14-5-15-25-34/h1-25H,26-29H2 N Key: AXVOAMVQOCBPQT-UHFFFAOYSA-N N InChI=1/C34H33P3/c1-6-16-30(17-7-1)35(26-28-36(31-18-8-2-9-19-31)32-20-10-3-11-21-32)27-29-37(33-22-12-4-13-23-33)34-24-14-5-15-25-34/h1-25H,26-29H2 Key: AXVOAMVQOCBPQT-UHFFFAOYAR
SMILES C1=CC=C(C=C1)P(CCP(C2=CC=CC=C2)C3=CC=CC=C3)CCP(C4=CC=CC=C4)C5=CC=CC=C5
Properties
Chemical formula	C34H29P3
Molar mass	534.55 g/mol
Appearance	white crystals
Melting point	129 to 130 °C (264 to 266 °F; 402 to 403 K)
Solubility in water	Insoluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Triphos

Names
IUPAC name 1,1,1-Tris(diphenylphosphinomethyl)ethane
Other names Triphos, tdppme, tdme
Identifiers
CAS Number	22031-12-5
3D model (JSmol)	Interactive image
ChemSpider	375165
PubChem CID	423856
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 °C (210 to 216 °F; 372 to 375 K)
Solubility in water	Insoluble
Hazards
Safety data sheet	Triphos MSDS
S-phrases (outdated)	22-24/25
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Triphos is the name for certain organophosphorus ligands. They are air-sensitive white solids that function as tridentate ligands in coordination and organometallic chemistry.

Bis(diphenylphosphinoethyl)phenylphosphine is called triphos, is a linear tridentate triphosphine. It is prepared by the free-radical-catalysed addition of phenylphosphine to vinyldiphenylphosphine:

This isomer of triphos is flexible and can bind to an octahedral metal center give either a facial or meridional isomers. Some derivatives are square planar complexes of the type [MX(triphos)]⁺ (M = Ni, Pd, Pt; X = halide).

1,1,1-Tris(diphenylphosphinomethyl)ethane is also called triphos. It is a tripodal ligand ("three-legged") of idealized C3v symmetry. It is prepared by the reaction of sodium diphenylphosphide and CH₃C(CH₂Cl)₃:

It forms complexes with many transition metals. It usually functions as a tripodal ligand that occupies three adjacent coordination sites. Triphos complexes often exhibit high thermal stability. Such complexes are used to analyze mechanistic aspects of homogeneous catalysts. 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.

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. 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.

Like bis(diphenylphosphinoethyl)phenylphosphine, bis(diphenylphosphinophenyl)phenylphosphine is a linear tridentate ligand, but it is more rigid and more air stable. It is prepared from o-lithiated triphenylphosphine: