1,1'-Bis(diphenylphosphino)ferrocene

1,1'-Bis(diphenylphosphino)ferrocene Basic information
Reaction
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.mol
1,1'-Bis(diphenylphosphino)ferrocene Structure
1,1'-Bis(diphenylphosphino)ferrocene Chemical Properties
Melting point 181-182 °C (dec.)(lit.)
storage temp. 2-8°C
solubility Chloroform, Ethyl Acetate
form crystal
color yellow to orange
Water Solubility Soluble in chloroform, dichloromethane, alcohol and pentane. Insoluble in water.
Sensitive Air Sensitive
Hydrolytic Sensitivity7: reacts slowly with moisture/water
Stability:Stable. Incompatible with strong oxidizing agents.
CAS DataBase Reference12150-46-8(CAS DataBase Reference)
NIST Chemistry Reference1,1'-Bis(diphenylphosphino)ferrocene(12150-46-8)
Safety Information
Hazard Codes T,Xi,Xn
Risk Statements 25-36/37/38-20/21/22
Safety Statements 22-24/25-45-28A-36-26-36/37/39
RIDADR 3467
WGK Germany 3
10-23
TSCA No
HazardClass IRRITANT
HS Code 29319090
MSDS Information
ProviderLanguage
SigmaAldrich English
ACROS English
ALFA English
1,1'-Bis(diphenylphosphino)ferrocene Usage And Synthesis
Reaction
  1. Ligand for Pd-catalyzed cross-coupling.
  2. Useful ligand for Pd-catalyzed carbon-nitrogen and carbon-oxygen bond forming procedures.
  3. Ligand for Ni-catalyzed amination of aryl chlorides.
  4. Ligand for Pd-catalyzed conversion of aryl halides to aryl nitriles.
  5. Ligand for Ni-catalyzed Suzuki reactions.
  6. Ni-catalyzed hydroamination of 1,3-dienes.
  7. Pd-catalyzed hydrocarbonation and hydroamination of 3,3-dihexylcyclopropene.
  8. Pd-catalyzed γ-arylation of β,γ-unsaturated ketones.
  9. Ligand for Ru-catalyzed reduction of nitriles to primary amines.
  10. Ligand for Rh-catalyzed alkyne head-to-tail dimerization.
  11. Ligand for Rh-catalyzed cross-coupling
  12. Ligand for Rh-catalyzed olefin isomerization
  13. Ligand for Ni or Rh-catalyzed borylation
  14. Ligand for regioselective Pd-catalyzed hydrophosphinylation of terminal alkynes to form branched alkenes.
Reactions of 12150-46-8_1
Reactions of 12150-46-8_2
Reactions of 12150-46-8_3

Chemical Properties1,1'-Bis(diphenylphosphino)ferrocene is deep yellow crystalline powder
Uses1,1'-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.
Uses1,1'-Bis(diphenylphosphino)ferrocene acts as a ligand in homogeneous catalysis. It is used as a ligand for ruthenium-catalyzed greener amine synthesis from amines and alcohols by hydrogen-borrowing. It is also employed as a ligand for Buchwald-Hartwig cross coupling. Further, it is used in the synthesis of coordination compound as well as the formation of complexes with various metals such as palladium chloride. In addition to this, it serves as a reagent for palladium-catalyzed coupling reactions and also plays an important role in Suzuki reaction.
General DescriptionNovel functionalized furan derivatives were prepared via Pd-phosphine sequential C-C and C-O bond formation.
Purification MethodsWash 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.]
Diphenylphosphine Ferrocene Diphenylphosphine oxide (R)-CTH-JAFAPHOS 1,1'-Bis(diphenylphosphino)ferrocene [1,1'-Bis(diphenylphosphino)ferrocene]tetracarbonylmolybdenum (S)-(R)-BPPFOH (1,1'-BIS(DIPHENYLPHOSPHINO)FERROCENE)TETRACARBONYLTUNGSTEN Chlorodiphenylphosphine (S)-N,N-DIMETHYL-1-[(R)-1',2-BIS(DIPHENYLPHOSPHINO)FERROCENYL]ETHYLAMINE N-(Carboxymethyl)-N-(phosphonomethyl)-glycine (1,1'-BIS(DIPHENYLPHOSPHINO)FERROCENE)TETRACARBONYLCHROMIUM (R)-(S)-BPPFOAC (S)-(R)-BPPFOH (R)-(S)-BPPFA (R)-(R)-BPPFOH (S)-(R)-BPPFOAC (ALPHAR,ALPHAR)-1,1'-BIS[ALPHA-(DIMETHYLAMINO)BENZYL]-(S,S)-,2'-BIS[BIS[3,5-BIS(TRIFLUOROMETHYL)PHENYL]PHOSPHINO]FERROCENE

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