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 C3v symmetry. It was originally prepared by the reaction of sodium diphenylphosphide and CH3C(CH2Cl)3:[1]

1,1,1-Tris(diphenylphosphinomethyl)ethane
Triphos.svg
Names
IUPAC name
1,1,1-Tris(diphenylphosphinomethyl)ethane
Other names
Triphos,
tdppme,
tdme
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.241.729 Edit this at Wikidata
EC Number
  • 811-359-5
  • 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
  • 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
C41H39P3
Molar mass 624.67 g/mol
Appearance white crystals
Melting point 99 to 102 °C (210 to 216 °F; 372 to 375 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
Safety data sheet (SDS) Triphos MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
3 Ph2PNa + CH3C(CH2Cl)3 → CH3C[CH2PPh2]3 + 3 NaCl

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)42-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]

Related ligandsEdit

ReferencesEdit

  1. ^ W. Hewertson & H. R. Watson (1962). "283. The preparation of di- and tri-tertiary phosphines". J. Chem. Soc.: 1490–1494. doi:10.1039/JR9620001490.
  2. ^ Huttner, G.; Strittmatter, J.; Sandhoefner, S. (2004). "Phosphorus Tripodal Ligands". Comprehensive Coordination Chemistry II. Vol. 1. pp. 297–322. doi:10.1016/B0-08-043748-6/01082-3. ISBN 9780080437484.{{cite encyclopedia}}: CS1 maint: uses authors parameter (link)
  3. ^ Bianchini, Claudio; Marchi, Andrea; Marvelli, Lorenza; Peruzzini, Maurizio; Romerosa, Antonio; Rossi, Roberto (1996). "Multiple Re-C Bonds at the [{MeC(CH2PPh2)3}Re(CO)2]+ Auxiliary". Organometallics. 15: 3804. doi:10.1021/om9602264.
  4. ^ Bianchini, Claudio; Meli, Andrea; Peruzzini, Maurizio; Vizza, Francesco (1990). "Tripodal Polyphosphine Ligands in Homogeneous Catalysis. 1. Hydrogenation and Hydroformylation of Alkynes and Alkenes Assisted by Organorhodium Complexes with MeC(CH2PPh2)3". Organometallics. 9: 226–240. doi:10.1021/om00115a035.
  5. ^ Cooper, Mervyn K.; Henrick, Kim; McPartlin, Mary & Latten, Jozef L. (1982). "The synthesis and X-ray structure of trichloro-1,1,1-(diphenylphosphinomethyl)ethanetrigold(I)". Inorganica Chimica Acta. 65 (2): L185. doi:10.1016/S0020-1693(00)93540-0.