[1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) Chemical Properties

Melting point:

275-280 °C(lit.)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Soluble in dichloromethane.

form 

powder

color 

red to very dark red

Stability:

Hygroscopic

InChI

InChI=1S/2C17H11P.2ClH.Fe.Pd/c2*1-3-9-15(10-4-1)18(17-13-7-8-14-17)16-11-5-2-6-12-16;;;;/h2*1-6,9-12,18H;2*1H;;/q;;;;+2;/p-2

InChIKey

LMSWLYFMTLONFK-UHFFFAOYSA-L

SMILES

[Cl-][Pd+2]1(P(C2C=CC=CC=2)(C2C=CC=CC=2)[C-]23C4=C5C6=C2[Fe+2]27893456C3C2=C7[C-]8(C9=3)P1(C1C=CC=CC=1)C1C=CC=CC=1)[Cl-]

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

20/21/22-36/37/38-40

Safety Statements 

23-24/25-26-36/37

WGK Germany 

3

TSCA 

No

HazardClass 

IRRITANT

HS Code 

28439000

Storage Class

6.1D - Non-combustible acute toxic Cat.3
toxic hazardous materials or hazardous materials causing chronic effects

Hazard Classifications

Carc. 1B Inhalation

[1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) Usage And Synthesis

Uses

[1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), is a palladium catalyst used in chemical synthesis of various compounds.Is used in preparation of Nucleosides as Ectonucleotidase inhibitors.

Chemical Properties

[1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) is Red solid

Uses

[1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) is used as a catalyst for Suzuki and Stile couplings.

Uses

suzuki reaction

Uses

Catalyst for C-C and C-N coupling reaction.

Application

[1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) may be used as an effective palladium catalyst in the following reactions:
Cross-coupling of sec-alkyl and n-alkyl Grignard reagents with high yield and selectivity.
Suzuki coupling of aryl boronic esters with [11C]methyl iodide to form functionalized [11C]toluene derivatives.
Kumada cross-coupling of 1,3,5-tribromobenzene with Grignard reagents to form star-shaped oligothiophenes.

reaction suitability

reagent type: catalyst
reaction type: Cross Couplings

Mechanism of action

[1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (pd(dppf)cl2) catalysis has gained widespread use in industrial and academic synthetic chemistry laboratories as a powerful methodology for the formation of C-C and C-Heteroatom bonds.

R = usually sp2 hybridised carbon
X = usually I, Br, Cl or OTf
The nature of R' and M are dependant upon
the specic coupling being performed

Synthesis

A method for the preparation of 1,1'-bis(diphenylphosphino)ferrocene palladium dichloride II (dppfPdCl2) comprising the steps of:

(a) adding palladium chloride to concentrated hydrochloric acid, heating to 40-80??C to dissolve, the amount of hydrochloric acid is 0.2-1.0 times the mass of palladium chloride, diluting with ethanol, the amount of ethanol is 10-50 times the mass of palladium chloride;

(b) bis-diphenylphosphinoferrocene (dppf) 3.0-5.0 times the mass of palladium chloride is added to a solution of tetrahydrofuran and heated to 40-80??C until dissolved, and the amount of tetrahydrofuran is 20-30 times the mass of palladium chloride;

(c) the solution obtained in step (a) was added dropwise to the solution obtained in step (b), and after the dropwise addition was completed, it was held at 45-80??C for 0.5-3h, and then cooled, filtered, washed, and dried in vacuum, to obtain 1,1'-bis(diphenylphosphino)ferrocene palladium dichloride II red crystals.

[1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II)(72287-26-4)Related Product Information

• Diphenylphosphine oxide
• Dicyclohexylchlorophosphine
• Chlorodiphenylphosphine
• ETHYNYLFERROCENE
• Tricyclohexyl phosphine
• Acetylferrocene
• Ferrocene
• Palladium chloride
• Tetrakis(triphenylphosphine)platinum
• [1,2-Bis(diphenylphosphino)ethane]dichloropalladium(II)
• Dichloro(1,5-cyclooctadien)ruthenium(II) polymer
• 1,1'-Bis (di-t-butylphosphino)ferrocene palladium dichloride,
• DICHLORO[1,3-BIS(DIPHENYLPHOSPHINO)PROPANE]PALLADIUM(II)
• ISOPROPYLDIPHENYLPHOSPHINE
• 1,1'-Bis(diphenylphosphino)ferrocene
• Dichloro(1,1-bis(diphenylphosphino)ferrocene)palladium(II) acetone adduct
• Palladium
• 1,3-Cyclopentadiene