Allylpalladium chloride dimer

Allylpalladium(II) chloride dimer

Names
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
3D model (JSmol)	Interactive image
ChemSpider	21171401 Y
ECHA InfoCard	100.031.423
PubChem CID	61538
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
SMILES Cl[Pd]CC=C.C=CC[Pd]Cl
Properties
Chemical 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
Safety data sheet	http://www.colonialmetals.com/pdf/5048.pdf
R-phrases (outdated)	36/37/38
S-phrases (outdated)	26-36
Related compounds
Related compounds	(η3-allyl)(η5 – cyclopentadienyl)palladium(II) di-μ-chlorobis(crotyl)dipalladium
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Allylpalladium(II) chloride dimer (APC) is a chemical compound with the formula [(η³-C₃H₅)PdCl]₂. This yellow air-stable compound is an important catalyst used in organic synthesis.^[1] It is one of the most widely used transition metal allyl complexes.

Synthesis and reactions

The compound is prepared by purging carbon monoxide through a methanolic aqueous solution of sodium tetrachloropalladate (prepared from palladium(II) chloride and sodium chloride), and allyl chloride.^[1]

2 Na₂PdCl₄   +   2 CH₂=CHCH₂Cl   +   2 CO   +   2 H₂O   →   [(η³-C₃H₅)PdCl]₂   +   4 NaCl   +   2 CO₂   +   4 HCl

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

[(η³-C₃H₅)PdCl]₂   +   2 NaC₅H₅   →   2 [(η⁵-C₅H₅)Pd(η³-C₃H₅)]   +   2 NaCl

References