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Palladium(II) chloride ChemBeads

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About This Item

Empirical Formula (Hill Notation):
Cl2Pd
CAS Number:
7647-10-1
Molecular Weight:
177.33
MDL number:
MFCD00003558
UNSPSC Code:
12352302
NACRES:
NA.22

form

solid

Quality Level

100

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)

Other Notes

High-Throughput Reaction Screening with Nanomoles of Solid Reagents Coated on Glass Beads

Versatile Methods to Dispense Sub-Milligram Quantities of Solids using Chemical Coated Beads for High-Throughput Experimentation

ChemBead Enabled High-Throughput Cross-Electrophile Coupling Reveals a New Complementary Ligand

Signal Word

Danger

Hazard Statements

H290,H317,H318,H350i,H410

Hazard Classifications

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

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

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Certificates of Analysis (COA)

Lot/Batch Number
MKCQ1029

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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.
Maozhong Miao et al.
Organic letters, 14(11), 2718-2721 (2012-05-16)
A novel PdCl(2)-catalyzed oxidative cycloisomerization of 3-cyclopropylideneprop-2-en-1-ones, providing a facile synthesis of highly strained functionalized 2-alkylidenecyclobutanones via furan-fused cyclobutene intermediates, is reported. An interesting route to 2(3H)-furanones with a spiro-cyclopropane unit from the obtained 2-alkylidenecyclobutanones via a ring-contraction rearrangement reaction
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
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
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ChemBeads, catalyst-coated glass beads, dispense solid chemical reagents for nanomole-scale high-throughput reaction screening.

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