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1,1'-Bis(diphenylphosphino)ferrocene

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CAS:12150-46-8
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CAS:12150-46-8
Purity:99% Package:100g,500g,1kg,5kg,10kg Remarks:Phosphorus Compounds
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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
form crystal
color yellow to orange
Water Solubility Soluble in chloroform, dichloromethane, alcohol and pentane. Insoluble in water.
Hydrolytic Sensitivity7: reacts slowly with moisture/water
Sensitive Air Sensitive
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
ACROS English
SigmaAldrich 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.


Chemical Properties1,1'-Bis(diphenylphosphino)ferrocene is deep yellow crystalline powder
Usessuzuki reaction
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.
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.]
Tag:1,1'-Bis(diphenylphosphino)ferrocene(12150-46-8) Related Product Information
1,3-Bis(diphenylphosphino)propane 1,2-Bis(diphenylphosphino)ethane nickel(II) chloride 1,2-Bis(diphenylphosphino)ethane (ALPHAS,ALPHAS)-1,1'-BIS[ALPHA-(DIMETHYLAMINO)BENZYL]-(R,R)-2,2'-BIS[BIS(2-METHYLPHENYL)PHOSPHINO]FERROCENE (ALPHAR,ALPHAR)-1,1'-BIS[ALPHA-(DIMETHYLAMINO)BENZYL]-(S,S)-2,2'-BIS[BIS(2-METHYLPHENYL)PHOSPHINO]FERROCENE (ALPHAS,ALPHAS)-1,1'-BIS[ALPHA-(DIMETHYLAMINO)BENZYL]-(R,R)-2,2'-BIS[DI(3,5-XYLYL)PHOSPHINO]FERROCENE (S)-(R)-BPPFOH (R)-(S)-BPPFOAC (S)-(R)-BPPFOAC (R)-(R)-BPPFOH (1,1'-BIS(DIPHENYLPHOSPHINO)FERROCENE)TETRACARBONYLCHROMIUM (R)-CTH-JAFAPHOS (1 1'-BIS(DIPHENYLPHOSPHINO)FERROCENE)T& (ALPHAR,ALPHAR)-1,1'-BIS[ALPHA-(DIMETHYLAMINO)BENZYL]-(S,S)-,2'-BIS[BIS[3,5-BIS(TRIFLUOROMETHYL)PHENYL]PHOSPHINO]FERROCENE (R)-(S)-BPPFA (S)-(R)-BPPFOH (1,1'-BIS(DIPHENYLPHOSPHINO)FERROCENE)TETRACARBONYLTUNGSTEN 1,1'-Bis(diphenylphosphino)ferrocene