Allylpalladium(II) Chloride Dimer Chemical Properties

Melting point:

120°C (dec.)

storage temp. 

2-8°C

form 

Crystals or Crystalline Powder

color 

Yellow to green-yellow

Water Solubility 

decomposes

Sensitive 

Air Sensitive

BRN 

4124623

NIST Chemistry Reference

[Pd(Cl)(C3H5)]2(12012-95-2)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-40

Safety Statements 

26-36-36/37

WGK Germany 

3

RTECS 

RT3510000

F 

1-10

TSCA 

No

HS Code 

28439090

MSDS

• Language:English Provider:Allylpalladium chloride dimer
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Allylpalladium(II) Chloride Dimer Usage And Synthesis

Chemical Properties

Allylpalladium(II) chloride dimer is a yellow powder with the formula [(η3-C3H5)PdCl]2. This compound is an important catalyst used in organic synthesis. It is one of the most widely used transition metal allyl complexes.

Uses

Allylpalladium(II) chloride dimer is used as an important catalyst in Heck reaction. It reacts with cyclopentadienyl anion to give cyclopentadienyl allyl palladium. It acts as a precatalyst for asymmetric and cross-coupling catalysis. Further, it is used in the preparation of 1,4-diallyl-1,2-dihydroisoquinolines. It is also employed as a catalyst for greener Buchwald-Hartwig coupling reaction and involved in the synthesis of cationic palladium catalysts. In addition, it takes part in preparation of -heterocyclic carbene-palladium-eta3-allyl chloride complex, which is an efficient catalyst for the Suzuki-Miyaura cross-coupling reactions in synthetic chemistry.

Uses

[Pd(allyl)Cl]2 can be used as a catalyst:
For the silylation of organobromides.
To synthesize α-aryl carbonyl compounds by coupling reaction between aldehydes and aryl halides.
To prepare various arylthiophene derivatives by cross-coupling reaction with aryl halides via C-H functionalization.
Application Guide for Palladium Catalyzed Cross-Coupling Reactions
ChemDose: Convenient Dosing of Catalysts and Reagents

Preparation

Allylpalladium(II) chloride dimer is prepared by purging carbon monoxide through a methanolic aqueous solution of palladium(II) chloride, sodium chloride, and allyl chloride.
2Na2PdCl4 + 2 CH2=CHCH2Cl + 2 CO + 2 H2O → (C3H5)2Pd2Cl2 + 4 NaCl + 2 CO2 + 4 HCl

Reactions

1. Precatalyst for the enantioselective hydrosilylation of olefins.
2. Precatalyst for asymmetric allylic alkylation and amination.
3. Used as a palladium source for cross-coupling reactions.
4. Can be used with Trost ligands.
5. Catalyst for the carbostannylation of alkynes.
6. Used as a precatalyst for "-arylation of aldehydes.

Allylpalladium(II) Chloride Dimer(12012-95-2)Related Product Information

• Rhodium triiodide
• Palladium(II) sulfate
• Gold(III) chloride
• Di-chlorobis[(1,2,3-)-1-phenyl-2-propenyl]dipalladium(II)
• Benzeneruthenium(II) chloride dimer
• Palladium chloride
• Stannous chloride dihydrate
• INDIUM(III) CHLORIDE TETRAHYDRATE
• PALLADIUM(II) NITRATE HYDRATE
• Chloro(1,5-cyclooctadiene)methylpalladium(II) 97%
• CHLORO(1,5-CYCLOOCTADIENE)(PENTAMETHYLCYCLOPENTADIENYL)RUTHENIUM (II)
• CHLORO[1,3-BIS(2,6-DI-I-PROPYLPHENYL)IMIDAZOL-2-YLIDENE]COPPER(I)
• Bis(tri-tert-butylphosphine)palladium(0)
• Bis(tricyclohexylphosphine)palladium(II) Dichloride
• Tetrakis(triphenylphosphine)platinum
• PALLADIUM(II) IODIDE
• Palladium (II) Acetate
• Palladium(II) oxide