Bis(diphenylphosphinoethyl)phenylphosphine

Bis(diphenylphosphinoethyl)phenylphosphine
Names
	IUPAC name Bis(diphenylphosphinoethyl)phenylphosphine
	Other names Triphos
Identifiers
CAS Number	23582-02-7 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL69711;
ChemSpider	81424 ;
ECHA InfoCard	100.041.579
EC Number	245-753-8;
PubChem CID	90192;
UNII	RL599PNU27 ;
CompTox Dashboard (EPA)	DTXSID70178220 ;
	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 Key: AXVOAMVQOCBPQT-UHFFFAOYSA-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
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
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Bis(diphenylphosphinoethyl)phenylphosphine is the organophosphorus compound with the formula [Ph₂PCH₂CH₂]₂PPh (Ph = C₆H₅). It is an air-sensitive white solid that function as tridentate ligands in coordination and organometallic chemistry.

It is prepared by the free-radical-catalysed addition of phenylphosphine to vinyldiphenylphosphine:^[1]

2 Ph₂PCH=CH₂ + H₂PPh → [Ph₂PCH₂CH₂]₂PPh

It 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).

Related ligands

diethylenetriamine (HN(CH₂CH₂NH₂)₂)
bis(diphenylphosphinophenyl)phenylphosphine^[2] (PhP(C₆H₄PPh₂)₂)
1,1,1-Tris(diphenylphosphinomethyl)ethane, a tripodal ligand.

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, Devon W. Meek J. Chem. Soc., Dalton Trans., 1975, 1011-1015.doi:10.1039/DT9750001011
^ Hartley, J. G., Venanzi, L. M., Goodall, D. C., "The Preparation and Complex-Forming Properties of One tritertiary and One Tetratertiary Phosphine", J. Chem. Soc. 1963, 3930. doi:10.1039/JR9630003930

[1] "Synthesis of Polytertiary Phosphines and ‘Mixed’ Phosphorus–Sulphur and ‘Mixed’ Phosphorus–Nitrogen Polydentate Ligands via Free-Radical Catalysis" Daniel L. DuBois, William H. Myers, Devon W. Meek J. Chem. Soc., Dalton Trans., 1975, 1011-1015.doi:10.1039/DT9750001011

[2] Hartley, J. G., Venanzi, L. M., Goodall, D. C., "The Preparation and Complex-Forming Properties of One tritertiary and One Tetratertiary Phosphine", J. Chem. Soc. 1963, 3930. doi:10.1039/JR9630003930

[1]

[2]