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205885

Sigma-Aldrich

Palladium(II) chloride

ReagentPlus®, 99%

Synonym(s):

Dichloropalladium, Palladium dichloride, Palladous chloride

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About This Item

Empirical Formula (Hill Notation):
Cl2Pd
CAS Number:
7647-10-1
Molecular Weight:
177.33
EC Number:
231-596-2
MDL number:
MFCD00003558
UNSPSC Code:
12161600
PubChem Substance ID:
24852359
NACRES:
NA.22

Quality Level

200

product line

ReagentPlus®

assay

99%

form

powder

reaction suitability

core: palladium
reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling
reagent type: catalyst

mp

678-680 °C (lit.)

density

4 g/mL at 25 °C (lit.)

SMILES string

Cl[Pd]Cl

InChI

1S/2ClH.Pd/h2*1H;/q;;+2/p-2

InChI key

PIBWKRNGBLPSSY-UHFFFAOYSA-L

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General description

Palladium(II) chloride is a widely used starting material for preparing other palladium catalysts, reagents, and nanoparticles.

Application

Application Guide for Palladium Catalyzed Cross-Coupling Reactions

Used in the synthesis of semiconducting metal-containing polymers in which the polypyrrole backbone has a conformational energy minimum and is nearly planar.
Palladium(II) chloride (PdCl2) can be used as a catalyst in the following processes:
  • PdCl2-CuCl2 catalytic system is used in the selective acetylation of 1o and 2o alkyl or aryl alcohols with vinyl acetate to prepare corresponding acetylated derivatives.
  • PdCl2–EDTA is used in the Suzuki cross-coupling reaction between aryl and heteroaryl halides with aryl(heteroaryl)boronic acids in water.
  • PdCl2-Cu(OAc)2 is used to synthesize polysubstituted pyrroles from phenethylamines via multiple deprotonations and deamination reactions.
  • PdCl2-PEG(300) is used in the Suzuki-Miyaura coupling reaction.
  • PdCl2-NaBH4 is used in the hydrogenation of carbon-carbon triple bonds to synthesize corresponding cis-alkenes in a polyethylene glycol-CH2Cl2 reaction medium.
  • PdCl2-(n-Bu)3N-NH4OOCH catalytic system is used in the synthesis of benzofurans via intramolecular Heck reaction.
For small-scale and high throughput uses, the product is also available as ChemBeads (919853)

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

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Hazard Classifications

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Storage Class

8B - Non-combustible corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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Certificates of Analysis (COA)

Lot/Batch Number
MKCR1114
MKCR0718
MKCQ4765
MKCQ2121
MKCQ0655

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Pd-EDTA as an efficient catalyst for Suzuki-Miyaura reactions in water
Korolev DN and Bumagin NA
Tetrahedron Letters, 46(34), 5751-5754 (2005)
PEG (300)-PdCl2 promoted efficient and convenient Suzuki-Miyaura coupling of aryl chlorides with arylboronic acids
Yin Liang, et al.
Tetrahedron, 62(40), 9359-9364 (2006)
Tetrahedron, 62, 9339-9339 (2006)
Farnaz Jafarpour et al.
The Journal of organic chemistry, 75(9), 3109-3112 (2010-04-14)
An atom-economical phosphane-free palladium-catalyzed direct C-2 arylation of unactivated free NH-pyrroles is devised. This method provides a straightforward route to a wide variety of substituted 2-aryl-1H-pyrroles from readily accessible starting materials. Iodoarenes bearing electron-withdrawing and electron-donating substituents are tolerated under
Yoshikazu Mori et al.
The Journal of organic chemistry, 68(4), 1571-1574 (2003-02-15)
Treatment of thiol esters 1 with zinc reagent 2 in the presence of a small amount (<ca. 1 mol %) of nonpyrophoric Pd(OH)(2)/C (Pearlman's catalyst) provided functionalized asymmetrical ketones 3 in high yields. The use of Pd(OH)(2)/C was further applied
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