Bis(diphenylphosphinoethyl)phenylphosphine

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.

Bis(diphenylphosphinoethyl)phenylphosphine
LinearTriphos.png
Names
IUPAC name
Bis(diphenylphosphinoethyl)phenylphosphine
Other names
Triphos
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.041.579 Edit this at Wikidata
EC Number
  • 245-753-8
  • 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
  • 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
C34H29P3
Molar mass 534.55 g/mol
Appearance white crystals
Melting point 129 to 130 °C (264 to 266 °F; 402 to 403 K)
Insoluble
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
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).
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Infobox references

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 ligandsEdit

ReferencesEdit

  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