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Palladium(II) chloride ChemBeads

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About This Item

Empirical Formula (Hill Notation):
Cl2Pd
CAS Number:
Molecular Weight:
177.33
MDL number:
UNSPSC Code:
12352302
NACRES:
NA.22

form

solid

Quality Level

composition

~ 4 wt.% loading of catalyst

reaction suitability

reagent type: catalyst
reaction type: Cross Couplings

SMILES string

Cl[Pd]Cl

InChI

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

InChI key

PIBWKRNGBLPSSY-UHFFFAOYSA-L

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.

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.

ChemBeads are chemical coated glass beads. ChemBeads offer improved flowability and chemical uniformity perfect for automated solid dispensing and high-throughput experimentation. The method of creating ChemBeads uses no other chemicals or surfactants allowing the user to accurately dispense sub-milligram amounts of chemical.

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For larger scale uses, product also available in powdered form (205885) & (520659)

Signal Word

Danger

Hazard Statements

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - Carc. 1B Inhalation - Eye Dam. 1 - Met. Corr. 1 - Skin Sens. 1

WGK

WGK 3

Regulatory Information

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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
Xiaobing Wan et al.
Journal of the American Chemical Society, 128(37), 12046-12047 (2006-09-14)
A unique method was discovered to construct polysubstituted pyrroles via an unprecedented multiple deprotonations/deaminations process from commercially available phenethylamines. During this transformation, twelve bonds were broken and five new bonds were constructed.
Juraj Velcicky et al.
Journal of the American Chemical Society, 133(18), 6948-6951 (2011-04-21)
A one-pot protocol for the cyanomethylation of aryl halides through a palladium-catalyzed reaction with isoxazole-4-boronic acid pinacol ester was developed. Mechanistically, the reaction proceeds through (1) Suzuki coupling, (2) base-induced fragmentation, and (3) deformylation as shown by characterization of all
Buyi Li et al.
Advanced materials (Deerfield Beach, Fla.), 24(25), 3390-3395 (2012-06-08)
Highly dispersed palladium chloride catalysts locked in triphenylphosphine-functionalized knitting aryl network polymers (KAPs) are developed and exhibit excellent activity under mild conditions in the Suzuki-Miyaura cross-coupling reactions of aryl chlorides in aqueous media. This work highlights that the microporous polymers
Yves Canac et al.
Inorganic chemistry, 50(21), 10810-10819 (2011-10-11)
The influence of the formal electrostatic interaction on the cis/trans coordination mode at a PdCl(2) center is investigated in a family of isostructural flexible diphosphine ligands Ph(2)P-X-C(6)H(4)-Y-PPh(2), where X and Y stand for neutral or cationic N,C-imidazolylene linkers. While the

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