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Merck
CN

683396

[Pd(allyl)Cl]2

greener alternative

≥98.0% (C, elemental analysis), solid, 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
NACRES:
NA.22
PubChem Substance ID:
329760817
UNSPSC Code:
12161600
EC Number:
234-579-8
Beilstein/REAXYS Number:
4124623

Key Documents

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Product Name

[Pd(allyl)Cl]2, Umicore

SMILES string

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

InChI key

TWKVUTXHANJYGH-UHFFFAOYSA-L

InChI

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

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

Quality Level

100

greener alternative product characteristics

Catalysis
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Greener Alternative Product

greener alternative category

Aligned

storage temp.

2-8°C

Related Categories

General description

We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for catalytic efficiency. Click here for more information.

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

signalword

Warning

hcodes

H315

Hazard Classifications

Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN2938
BCCM1566
BCCK5039
BCCG7046
BCCH3382

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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)
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 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)

Articles

Palladium-catalyzed Cross-coupling Reactions

A variety of palladium-catalyzed cross-coupling reactions can be run under room temperature conditions in water with TPGS- 750-M, using a variety of commercially available palladium complexes and ligands.

Umicore Precatalysts

Precatalysts for asymmetric catalysis offer batch-to-batch consistency in a range of catalytic reactions, supporting diverse research needs.

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