1,1'-Bis(diphenylphosphino)ferrocene

Superiority:

Product Name:    1,1'-Bis(diphenylphosphino)ferrocene
Synonyms:    DPPF;1,1''-BIS(DIPHENYLPHOSPHINO)ERROCENE;1,1''-BIS(DIPHENYLPHOSPHINO)FERROCENE (DPPF);DPPF/1,1''-BIS(DIPHENYLPHOSPHINO) FERROCENE;1,1'-Bis(diphenylphosphiNA)ferrocene;DPPF, (Ferrocene-1,1'-diyl)bis(diphenylphosphine);1,1-(twophenylphosphine)Er Maotie;1,1'-BIS(DIPHENYLPHOSPHINO)FERROCENE
CAS:    12150-46-8
MF:    C34H28FeP210*
MW:    554.38
EINECS:    640-119-0
Product Categories:    Miscellaneous;pharmacetical;Ligand;Catalysts-Ligands;Classes of Metal Compounds;Fe (Iron) Compounds;Boron, Nitrile, Thio,& TM-Cpds;Ferrocenes;Metallocenes;Phosphine Ligands;Synthetic Organic Chemistry;Transition Metal Compounds;Aromatics;Catalyst;Phosphines;Chelating Agents & Ligands;Pharmaceutical intermediates;Achiral Phosphine;Aryl Phosphine
Mol File:    12150-46-8.molMelting point     181-182 °C (dec.)(lit.)
storage temp.     2-8°C
form     crystal
color     yellow to orange
Water Solubility     Soluble in chloroform, dichloromethane, alcohol and pentane. Insoluble in water.
Hydrolytic Sensitivity    7: reacts slowly with moisture/water
Sensitive     Air Sensitive
Stability:    Stable. Incompatible with strong oxidizing agents.
CAS DataBase Reference    12150-46-8(CAS DataBase Reference)
NIST Chemistry Reference    1,1'-Bis(diphenylphosphino)ferrocene(12150-46-8

Reaction    
Ligand for Pd-catalyzed cross-coupling.
Useful ligand for Pd-catalyzed carbon-nitrogen and carbon-oxygen bond forming procedures.
Ligand for Ni-catalyzed amination of aryl chlorides.
Ligand for Pd-catalyzed conversion of aryl halides to aryl nitriles.
Ligand for Ni-catalyzed Suzuki reactions.
Ni-catalyzed hydroamination of 1,3-dienes.
Pd-catalyzed hydrocarbonation and hydroamination of 3,3-dihexylcyclopropene.
Pd-catalyzed γ-arylation of β,γ-unsaturated ketones.
Ligand for Ru-catalyzed reduction of nitriles to primary amines.
Ligand for Rh-catalyzed alkyne head-to-tail dimerization.
Ligand for Rh-catalyzed cross-coupling
Ligand for Rh-catalyzed olefin isomerization
Ligand for Ni or Rh-catalyzed borylation
Ligand for regioselective Pd-catalyzed hydrophosphinylation of terminal alkynes to form branched alkenes.\

hemical Properties    1,1'-Bis(diphenylphosphino)ferrocene is deep yellow crystalline powder
Uses    suzuki reaction
Uses    1,1'-Bis(diphenylphosphino)ferrocene used coordination compound in synthesis, readily forms complexes with various metals, i.e. when reacting with the acetonitrile or benzonitrile complexes of PdCl2 it forms (dppf)PdCl2, which i s a popular reagent for palladium-catalyzed coupling reactions.
Purification Methods    Wash it with distilled H2O and dry it in a vacuum. Dissolve it in ca 5 parts of hot dioxane and cool to give orange crystals m 181-183o. Recrystallisation from *C6H6/heptane (1:2) gives a product with m 183-184o. [Bishop et al. J Organomet Chem 27 241 1971.]
1,1'-Bis(diphenylphosphino)ferrocene Preparation Products And Raw materials
Raw materials    Sodium hydroxide-->Ethyl acetate-->Tetrahydrofuran-->DCM-->n-Butyllithium-->N,N,N',N'-Tetramethylethylenediamine-->Ferrocene-->Dicyclopentadiene-->Ferrous chloride-->Chlorodiphenylphosphine-->Lithium, [1-(diphenylphosphino)-2,4-cyclopentadien-1-yl]--->Diphenylphosphinoferrocene-->1,1'-bis(diphenylphosphinyl)-Ferrocene-->4,4'-Bis(t-butyl)-1,1',2,2'-tetrakis(diphenylphosphino)ferrocene, 98% HiersoPHOS-5-->DIMETHYLPHENYLPHOSPHINE-->Sodium thiocyanate-->Sodium diethyldithiocarbamate-->Phenyllithium