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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

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

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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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)
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)
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)

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