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520659

Sigma-Aldrich

Palladium(II) chloride

≥99.9%

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Synonym(s):
Dichloropalladium, Palladium dichloride, Palladous chloride
Empirical Formula (Hill Notation):
Cl2Pd
CAS Number:
Molecular Weight:
177.33
EC Number:
MDL number:
UNSPSC Code:
12352300
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

≥99.9%

composition

Pd, 59-60%

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 (PdCl2) reacts with unsubstituted or alkyl-substituted cyclic ketones in the CO atmosphere to afford acyclic diesters and acyclic chloro-substituted monoesters. PdCl2 reacts with N,N-dimethylallylamine in methanol to afford di-μ-chloro-bis(2-methoxy-3-N,N-dimethylaminopropyl)dipalladium(II). Palladium dichloride, acetate and acetylacetonate in the [bmim][BF4] or [bmim][PF6] (where[bmim]+ = 1-butyl-3-methylimidazolium cation) ionic liquids have been employed for the hydrodimerization of butadiene to form octa-2,7-dien-1-ol.

Palladium(II) chloride is used as an oxidizing agent and catalyst for the Suzuki-Miyaura and Mizoroki-Heck reactions.

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) was used in the following studies:
  • As catalyst for the carbonylation of organic tellurides by reaction with carbon monoxide.
  • As a catalyst along with Cu(II) for the deamination of phenethylamines to phenyl substituted pyrroles.
  • Together with PEG 300, promoted efficient Suzuki-coupling of aryl chlorides with aryl boronic acids.
For small scale and high throughput uses, product is also available as ChemBeads (919853)

Signal Word

Danger

Hazard Statements

Hazard Classifications

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

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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The Formation of Carbon to Metal s Complexes between Palladium (II) Chloride and Allylic Amines.
Cope AC, et al.
Journal of the American Chemical Society, 89(2), 287-291 (1967)
Oxadiazoline and Ketoimine Palladium (II) Complexes as Highly Efficient Catalysts for Suzuki--Miyaura Cross-Coupling Reactions in Supercritical Carbon Dioxide
Fernandes RR, et al.
Advanced Synthesis & Catalysis, 353(7), 1153-1160 (2011)
Yuka, Kawashita; et al.
Tetrahedron Letters, 47, 4231-4233 (2006)
Journal of the American Chemical Society, 126, 12046-12046 (2006)
Room-Temperature Ionic Liquids. Solvents for Synthesis and Catalysis.
Thomas Welton
Chemical reviews, 99(8), 2071-2084 (2002-02-19)

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