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12150-46-8

12150-46-8 Structure

12150-46-8 Structure
IdentificationMore
[Name]

1,1'-Bis(diphenylphosphino)ferrocene
[CAS]

12150-46-8
[Synonyms]

1,1'-BIS(DIPHENYLPHOSPHINO)FERROCENE
1,1'-FERROCENEBIS(DIPHENYLPHOSPHINE)
1,1'-FERROCENEDIYL-BIS(DIPHENYLPHOSPHINE)
DPPF
1,1'-bis(diphenyphosphino)ferrocene
1,1'-bis(diphenyphosphino)ferrocene(dppf)
1,1'-BIS(DIPHENYLPHOSPHINO)FERROCENE, 97 %
1,1'-Bis(diphenylphosphino)ferrocene,99%DPPF
1,1''-BIS(DIPHENYLPHOSPHINO)ERROCENE
1,1''-BIS(DIPHENYLPHOSPHINO)FERROCENE (DPPF)
DPPF/1,1''-BIS(DIPHENYLPHOSPHINO) FERROCENE
1,1''-BIS-(DIPHENYLPHOSPHINO)-FEROCENE
1,1'-Bis(diphenylphosphino) ferrocene, Catalyst Grade
1,1'-Bis(diphenylphosphino)ferrocene, C 73.4%, H 5.2%
1,1μ-Ferrocenebis(diphenylphosphine), 1,1μ-Ferrocenediyl-bis(diphenylphosphine)
[EINECS(EC#)]

430-420-3
[Molecular Formula]

C34H28FeP2 10*
[MDL Number]

MFCD00001422
[Molecular Weight]

554.38
[MOL File]

12150-46-8.mol
Chemical PropertiesBack Directory
[Appearance]

deep yellow crystalline powder
[Melting point ]

181-182 °C (dec.)(lit.)
[mp ]

181-182 °C (dec.)(lit.)
[storage temp. ]

2-8°C
[form ]

crystal
[color ]

yellow to orange
[Stability:]

Stable. Incompatible with strong oxidizing agents.
[Water Solubility ]

Soluble in chloroform, dichloromethane, alcohol and pentane. Insoluble in water.
[Hydrolytic Sensitivity]

7: reacts slowly with moisture/water
[Sensitive ]

Air Sensitive
[Detection Methods]

HPLC
[CAS DataBase Reference]

12150-46-8(CAS DataBase Reference)
[NIST Chemistry Reference]

1,1'-Bis(diphenylphosphino)ferrocene(12150-46-8)
[Storage Precautions]

Air sensitive
Safety DataBack Directory
[Hazard Codes ]

T,Xi,Xn
[Risk Statements ]

R25:Toxic if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
[Safety Statements ]

S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
[RIDADR ]

3467
[WGK Germany ]

3
[F ]

10-23
[TSCA ]

No
[HazardClass ]

IRRITANT
[HS Code ]

29319099
Raw materials And Preparation ProductsBack Directory
【Raw materials】

Sodium hydroxide-->Ethyl acetate-->Tetrahydrofuran-->Dichloromethane-->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
【Preparation Products】

[1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II)-->N,N'-Bis- (1-naphthalenyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine-->1,1'-Bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex-->[1,1'-Bis(diphenylphosphino)ferrocene]dichloronickel(II)
Hazard InformationBack Directory
[Chemical Properties]

1,1'-Bis(diphenylphosphino)ferrocene is deep yellow crystalline powder
[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.
[Uses]

suzuki reaction
[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.]
Questions And AnswerBack Directory
[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.


Well-known Reagent Company Product InformationBack Directory
[Alfa Aesar]

1,1'-Bis(diphenylphosphino)ferrocene, 97%(12150-46-8)
[TCI AMERICA]

1,1'-Bis(diphenylphosphino)ferrocene,>96.0%(T)(12150-46-8)
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