Allylpalladium chloride dimer

Allylpalladium(II) chloride dimer
IUPAC name Allylpalladium(II) chloride dimer
Other names Allylpalladium chloride dimer bis(allyl)di-μ-chloro-dipalladium(II) APC
Identifiers
CAS number	12012-95-2 Y
ChemSpider	21171401 Y
Jmol-3D images	Image 1
SMILES Cl[Pd]CC=C.C=CC[Pd]Cl
InChI InChI=1S/2C3H5.2ClH.2Pd/c2*1-3-2;;;;/h2*3H,1-2H2;2*1H;;/q;;;;2*+1/p-2 Y Key: TWKVUTXHANJYGH-UHFFFAOYSA-L Y InChI=1/2C3H5.2ClH.2Pd/c2*1-3-2;;;;/h2*3H,1-2H2;2*1H;;/q;;;;2*+1/p-2/r2C3H5ClPd/c2*1-2-3-5-4/h2*2H,1,3H2 Key: TWKVUTXHANJYGH-NNVIZEFPAF
Properties
Molecular formula	C6H10Cl2Pd2
Molar mass	365.85 g/mol
Appearance	Pale yellow, crystalline solid
Density	Solid
Melting point	decomp at 155-156 °C
Solubility in water	Insoluble
Solubility in other solvents	Chloroform benzene acetone methanol
Hazards
MSDS	http://www.colonialmetals.com/pdf/5048.pdf
R-phrases	36/37/38
S-phrases	26-36
Related compounds
Related compounds	(η3-allyl)(η5 – cyclopentadienyl)palladium(II) di-μ-chlorobis(crotyl)dipalladium
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Allylpalladium(II) chloride dimer is a chemical compound with the formula (η³- C₃H₅)₂Pd₂Cl₂. This yellow air-stable compound is an important catalyst used in organic synthesis.

Synthesis and reactions

The compound 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

APC reacts with sources of cyclopentadienyl anion to give the corresponding 18e complex cyclopentadienyl allyl palladium:

(C₃H₅)₂Pd₂Cl₂ + 2 NaC₅H₅ → 2 Pd(η³-C₃H₅)(η⁵-C₅H₅) + 2 NaCl