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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

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

related product

Product No.
Description
Pricing

Signal Word

Danger

Hazard Statements

H290,H302,H317,H318,H410

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1 - Met. Corr. 1 - Skin Sens. 1

Storage Class Code

8B - Non-combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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