Skip to Content
Merck
All Photos(6)

Key Documents

View All Documentation

222380

Sigma-Aldrich

Allylpalladium(II) chloride dimer

greener alternative

98%

Synonym(s):

Bis((η3-allyl)(chloro)palladium), Di-ο-allyldi-μ-chlorodipalladium, [PdCl(C3H5)]2

Sign Into View Organizational & Contract Pricing
All Photos(6)

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:
24853328
NACRES:
NA.22

Quality Level

200

Assay

98%

form

solid

reaction suitability

core: palladium
reaction type: Cross Couplings
reagent type: catalyst
reaction type: C-H Activation

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

greener alternative category

, Aligned

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

Looking for similar products? Visit Product Comparison Guide

Related Categories

General description

Allylpalladium(II) chloride dimer is employed as catalyst in Heck reaction. It also participates as catalyst in the tandem nucleophilic allylation-alkoxyallylation reaction of the alkynylaldehydes with allyl chloride and allyltributylstannane.
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
Allylpalladium(II) chloride dimer has been employed for the following studies:
  • Synthesis of cationic palladium cataysts, used in the microwave-assisted Heck arylation.
  • Synthesis of N-heterocyclic carbene-palladium-η3-allyl chloride complexes, which are efficient catalyst for the Suzuki-Miyaura cross-coupling of aryl bromides and activated aryl chlorides.
  • Synthesis of 1,4-diallyl-1,2-dihydroisoquinolines.
  • As catalyst for greener Buchwald-Hartwig coupling in TPGS-750-M.

On the Way Towards Greener Transition-Metal-Catalyzed Processes as Quantified by E Factors

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKCQ5300
MKCM2584
MKCM4085
MKCL8373
MKCK4418

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

An N-heterocyclic carbene-palladium-η3-allyl chloride complex for the Suzuki-Miyaura coupling of aryl halides.
Broekemier NW, et al.
European Journal of Chemistry, 5(1), 162-166 (2014)
Radetich, B.; RajanBabu, T. V.
Journal of the American Chemical Society, 120, 8007-8007 (1998)
Yasuyuki Harada et al.
Organic letters, 7(20), 4385-4387 (2005-09-24)
[reaction: see text] The reaction of yne esters with carbon monoxide (1 atm) in the presence of palladium complexes gives bicyclic unsaturated lactone derivatives in good to high yields. The 2-pyridinyloxy group is a good leaving group among leaving groups
Superhydrophobicity of nanostructured carbon films in a wide range of pH values.
Lin Feng et al.
Angewandte Chemie (International ed. in English), 42(35), 4217-4220 (2003-09-23)
Tandem nucleophilic allylation-alkoxyallylation of alkynylaldehydes via amphiphilic bis-p-allylpalladium complexes.
Nakamura H, et al.
Tetrahedron Letters, 43(42), 7631-7633 (2002)
View All Related Papers

Articles

Procedures for Transition-Metal-Catalyzed Cross-Coupling Reactions in Water at Room Temperature using TPGS-750-M

TPGS-750-M, a second generation surfactant, is useful for room temperature, palladium and ruthenium-catalyzed reactions in water. Reactions include the Heck reaction, Suzuki-Miyaura reaction, Sonogashira reaction, Buchwald-Hartwig amination reaction, Negishi reaction, and olefin metathesis.

Heck Reaction Applications & Products

The Heck reaction is the palladium catalyzed cross-coupling reaction between alkenes and aryl or vinyl halides (or triflates) to afford substituted alkenes.

Protocols

Buchwald-Hartwig Amination Reaction in Water at Room Temperature using TPGS-750-M

TPGS-750-M, a second generation surfactant, may be used in the Buchwald-Hartwig Amination Reaction in Water at Room Temperature.

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

Contact Technical Service