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683396

Sigma-Aldrich

[Pd(allyl)Cl]2

Umicore

Synonym(s):

Allylpalladium(II) chloride dimer, Allylchloropalladium dimer, Bis(η3-allyl)di(μ-chloro)dipalladium(II), Bis(allyl)dichlorodipalladium, Bis(allyl)dichloropalladium, Bis(allylchloropalladium), Diallyldichlorodipalladium, [PdCl(C3H5)]2

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About This Item

Empirical Formula (Hill Notation):
C6H10Cl2Pd2
CAS Number:
12012-95-2
Molecular Weight:
365.89
Beilstein:
4124623
EC Number:
234-579-8
MDL number:
MFCD00044874
UNSPSC Code:
12161600
PubChem Substance ID:
329760817
NACRES:
NA.22

Quality Level

100

Assay

≥98.0% (C, elemental analysis)

form

solid

reaction suitability

core: palladium
reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Cross Couplings
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

storage temp.

2-8°C

SMILES string

Cl[Pd]CC=C.Cl[Pd]CC=C

InChI

1S/2C3H5.2ClH.2Pd/c2*1-3-2;;;;/h2*3H,1-2H2;2*1H;;/q;;;;2*+1/p-2

InChI key

TWKVUTXHANJYGH-UHFFFAOYSA-L

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Application

Application Guide for Palladium Catalyzed Cross-Coupling Reactions
[Pd(allyl)Cl]2 can be used as a catalyst:
  • For the silylation of organobromides.
  • To synthesize α-aryl carbonyl compounds by coupling reaction between aldehydes and aryl halides.
  • To prepare various arylthiophene derivatives by cross-coupling reaction with aryl halides via C-H functionalization.

Other Notes

Umicore Precatalysts for Asymmetric and Cross-Coupling Catalysis

Legal Information

Product of Umicore

Additional information available at www.pmc.umicore.com

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315

Hazard Classifications

Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCG7046
BCCF6033
BCCF7347
BCCD8863
BCCB6450

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Synthesis of HOMSi Reagents by Pd/Cu-Catalyzed Silylation of Bromoarenes with Disilanes
Minami Y, et al.
Chemistry Letters (Jpn), 43(2), 201-203 (2014)
Direct Arylation of Thiophenes via Palladium-Catalysed C-H Functionalisation at Low Catalyst Loadings
Battace A, et al.
Advanced Synthesis & Catalysis, 349(16), 2507-2516 (2007)
Palladium-catalyzed alpha-arylation of aldehydes with bromo- and chloroarenes catalyzed by [{Pd(allyl)Cl}2] and dppf or Q-phos
Giang D Vo and John F Hartwig
Angewandte Chemie (International Edition in English), 2127-2130 (2008)
Direct Arylation of Thiophenes via Palladium-Catalysed C-H Functionalisation at Low Catalyst Loadings
Battace A, et al.
advanced synthesis and catalysis, 349(16), 2507-2516 (2007)
Palladium-catalyzed alpha-arylation of aldehydes with bromo- and chloroarenes catalyzed by [{Pd(allyl)Cl}2] and dppf or Q-phos
Giang D Vo and John F Hartwig
Angewandte Chemie (International ed. in English), 2127-2130 (2008)

Articles

Umicore Precatalysts

We are happy to offer a series of precatalysts for asymmetric catalysis and Pd based cross coupling catalysis. Our partnership with Umicore allows us to offer a portfolio of metal complexes with batch-to-batch consistency for a plethora of catalytic reactions. 20 different precatalyst complexes are available, providing access to hundred different catalytic reactions.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

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