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ChemicalBook > CAS DataBase List > 1,1'-Bis(diphenylphosphino)ferrocene

1,1'-Bis(diphenylphosphino)ferrocene

Reaction
Product Name
1,1'-Bis(diphenylphosphino)ferrocene
CAS No.
12150-46-8
Chemical Name
1,1'-Bis(diphenylphosphino)ferrocene
Synonyms
DPPF;Bis(diphenylphosphino)ferrocene;1,1'-FERROCENEDIYL-BIS(DIPHENYLPHOSPHINE);98% DPPF;DPPF ChemBeads;1,1'-Bis(diphenylpho;Terazolamide Impurity 83;Zirconium ionophore I ;phosphino)ferrocene (DPPF);1,1-(twophenylphosphine)Er Maotie
CBNumber
CB2746748
Molecular Formula
C34H28FeP210*
Formula Weight
554.38
MOL File
12150-46-8.mol
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1,1'-Bis(diphenylphosphino)ferrocene Property

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 Sensitivity
7: reacts slowly with moisture/water
Stability:
Stable. Incompatible with strong oxidizing agents.
InChI
InChI=1S/2C17H14P.Fe/c2*1-3-9-15(10-4-1)18(17-13-7-8-14-17)16-11-5-2-6-12-16;/h2*1-14H;
InChIKey
HPXNTHKXCYMIJL-UHFFFAOYSA-N
SMILES
P(C1C=CC=CC=1)(C1=CC=CC=C1)[C]1[CH][CH][CH][CH]1.P(C1=CC=CC=C1)(C1=CC=CC=C1)[C]1[CH][CH][CH][CH]1.[Fe] |^1:13,14,15,16,17,31,32,33,34,35|
CAS DataBase Reference
12150-46-8(CAS DataBase Reference)
NIST Chemistry Reference
1,1'-Bis(diphenylphosphino)ferrocene(12150-46-8)
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Safety

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
F 
10-23
TSCA 
No
HazardClass 
IRRITANT
HS Code 
29319090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
177261
Product name
1,1′-Bis(diphenylphosphino)ferrocene
Purity
97%
Packaging
1g
Price
$35.84
Updated
2025/07/31
Sigma-Aldrich
Product number
936669
Product name
DPPF ChemBeads
Packaging
1 unit
Price
$139
Updated
2025/07/31
Sigma-Aldrich
Product number
177261
Product name
1,1′-Bis(diphenylphosphino)ferrocene
Purity
97%
Packaging
10g
Price
$202.79
Updated
2025/07/31
TCI Chemical
Product number
B2027
Product name
1,1'-Bis(diphenylphosphino)ferrocene
Purity
>96.0%(T)
Packaging
1g
Price
$26
Updated
2025/07/31
TCI Chemical
Product number
B2027
Product name
1,1'-Bis(diphenylphosphino)ferrocene
Purity
>96.0%(T)
Packaging
5g
Price
$46
Updated
2025/07/31
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1,1'-Bis(diphenylphosphino)ferrocene Chemical Properties,Usage,Production

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 Properties

1,1'-Bis(diphenylphosphino)ferrocene is deep yellow crystalline powder

Uses

1,1'-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.

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.

General Description

Novel functionalized furan derivatives were prepared via Pd-phosphine sequential C-C and C-O bond formation.

reaction suitability

reaction type: Cross Couplings
reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction
reagent type: ligand
reaction type: Carbonylations
reagent type: ligand
reaction type: Ene Reaction
reagent type: ligand
reaction type: Heck Reaction
reagent type: ligand
reaction type: Negishi Coupling
reagent type: ligand
reaction type: Sonogashira Coupling
reagent type: ligand
reaction type: Stille Coupling
reagent type: ligand
reaction type: Suzuki-Miyaura Coupling
reagent type: ligand
reaction type: Tsuji-Trost Reaction

Synthesis

405164-68-3

12150-46-8

The general procedure for the synthesis of 1,1'-bis(diphenylphosphino)ferrocene (dppf) from the compound (CAS: 405164-68-3) is as follows: Example 4: 100 mg (0.171 mmol) of 1,1'-bis(diphenoxyphosphino)ferrocene was reacted with 4 mg (16 μmol) of I? and 170 μL (0.68 mmol) of tributylphosphine in 1 mL of acetonitrile/THF (1:1, v/v) mixed solvent. The reaction mixture was stirred at room temperature for 10 min under nitrogen protection, followed by quenching the reaction with 100 μL of H?O. The reaction was then quenched with 10 mL of ethyl acetate. The reaction mixture was diluted with 10 mL of ethyl acetate and washed three times (5 mL each) with saturated aqueous NaHCO?solution. The organic phase was dried with Na?SO?, filtered and concentrated under reduced pressure. The resulting residue was recrystallized with ethanol, the crystals were collected by filtration, washed and dried under vacuum to give 89 mg (0.160 mmol, 94% yield) of 1,1'-bis(diphenylphosphino)ferrocene (dppf).

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.]

References

[1] Patent: WO2011/123037, 2011, A1. Location in patent: Page/Page column 23

1,1'-Bis(diphenylphosphino)ferrocene Preparation Products And Raw materials

Raw materials

Ferrocene N,N,N',N'-Tetramethylethylenediamine Dicyclopentadiene Ferrous chloride Chlorodiphenylphosphine Tetrahydrofuran Ethyl acetate Dichloromethane Sodium hydroxide n-Butyllithium

Preparation Products

N,N'-Di-1-naphthyl-N,N'-diphenylbenzidine (NPB) 1,1'-Bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex [1,1'-Bis(diphenylphosphino)ferrocene]dichloronickel(II) [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II)
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View Lastest Price from 1,1'-Bis(diphenylphosphino)ferrocene manufacturers

HANGZHOU HAILAN CHEMICAL CO.,LTD.
Product
1,1'-Bis(diphenylphosphino)ferrocene 12150-46-8
Price
US $0.00/kg
Min. Order
1kg
Purity
99%min
Supply Ability
2000kgs
Release date
2025-10-21
WUHAN FORTUNA CHEMICAL CO., LTD
Product
1,1'-Bis(diphenylphosphino)ferrocene(DPPF) 12150-46-8
Price
US $390.00-238.00/KG
Min. Order
0.1KG
Purity
99% HPLC
Supply Ability
100KG
Release date
2021-06-05
Hebei Chuanghai Biotechnology Co., Ltd
Product
1,1'-Bis(diphenylphosphino)ferrocene 12150-46-8
Price
US $10.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
5tons
Release date
2024-12-04

12150-46-8, 1,1'-Bis(diphenylphosphino)ferroceneRelated Search:

Ferrocene Diphenylphosphine oxide Diphenylphosphine Chlorodiphenylphosphine N-(Carboxymethyl)-N-(phosphonomethyl)-glycine 1,3-Bis(diphenylphosphino)propane 1,2-Bis(diphenylphosphino)ethane nickel(II) chloride 1,2-Bis(diphenylphosphino)ethane (1,1'-BIS(DIPHENYLPHOSPHINO)FERROCENE)TETRACARBONYLCHROMIUM (S)-N,N-DIMETHYL-1-[(R)-1',2-BIS(DIPHENYLPHOSPHINO)FERROCENYL]ETHYLAMINE (R)-CTH-JAFAPHOS Dichloro(1,1-bis(diphenylphosphino)ferrocene)palladium(II) acetone adduct [1,1'-Bis(diphenylphosphino)ferrocene]dichloronickel(II) [1,1'-Bis(diphenylphosphino)ferrocene]dichlorocobalt(II) [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (ALPHAR,ALPHAR)-1,1'-BIS[ALPHA-(DIMETHYLAMINO)BENZYL]-(S,S)-2,2'-BIS(DIPHENYLPHOSPHINO)FERROCENE (ALPHAR,ALPHAR)-1,1'-BIS[ALPHA-(DIMETHYLAMINO)BENZYL]-(S,S)-2,2'-BIS[BIS(4-METHOXY-3,5-DIMETHYLPHENYL)PHOSPHINO]FERROCENE 1,1'-Bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex

  • 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'-FERROCENEDIYL-BIS(DIPHENYLPHOSPHINE)
  • 1,1'-FERROCENEBIS(DIPHENYLPHOSPHINE)
  • 1,1'-bis(diphenyphosphino)ferrocene
  • 1,1'-bis(diphenyphosphino)ferrocene(dppf)
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  • bis(2-(diphenylphosphino)cyclopenta-2,4-dien-1-yl)iron
  • dppf 1,1'-Ferrocenebis(diphenylphosphine) 1,1'-Ferrocenediyl-bis(diphenylphosphine)
  • Zirconium ionophore I
  • Ferrocene,1,1'-bis(diphenylphosphino)-
  • 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)
  • 1,1''-BIS-(DIPHENYLPHOSPHINO)-FEROCENE
  • 1,1'-Bis(diphenylphosphino)ferrocene,98%
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  • 1'-Bis(diphenylphosphino)ferrocene
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  • 98% DPPF
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  • cyclopenta-2,4-dien-1-yl(diphenyl)phosphane(1:2)
  • DPPF (1,1-Bis(Diphenylphosphino)Ferrocene) extrapure, 98%
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  • 1,1'-Bis(diphenylphosphino)ferrocene
  • 1,1'- bis (diphenylphosphine) ferrocene
  • 1,1'-Bis(diphenylphosphino)ferrocene (Dppf)
  • Ferrocene, 1,1'-bis(diphenylphosphino)-
  • Terazolamide Impurity 83
  • 1,1'-Bis(diphenylphosphino)ferrocene, 94%
  • DPPF ChemBeads
  • 1,1′-Bis(diphenylphosphino)ferrocene, CAS 12150-46-8
  • 1,1'-Bis(diphenylphosphino)ferrocene
  • 12150-46-8
  • C34H28FeP2
  • C35H30Cl2FeP2
  • C6H52PC5H4FeC5H4PC6H52
  • Polydentate Phosphine Ligands
  • Phosphorus Compounds
  • Fe (Iron) Compounds