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Bis(diphenylphosphinoethyl)phenylphosphine

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Bis(diphenylphosphinoethyl)­phenylphosphine
Names
Preferred IUPAC name bis(diphenylphosphane)
Other names Triphos
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.041.579 Edit this at Wikidata
EC Number
  • 245-753-8
PubChem CID
UNII
CompTox Dashboard (EPA)
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,26-29H2Key: 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,26-29H2Key: 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 GHS07: Exclamation mark
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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Bis(diphenylphosphinoethyl)phenylphosphine is the organophosphorus compound with the formula 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:

2 Ph2PCH=CH2 + H2PPh → 2PPh

It can bind to an octahedral metal center to give either a facial or meridional isomers. Some derivatives are square planar complexes of the type (M = Ni, Pd, Pt; X = halide).

Related ligands

References

  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
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