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520764 Aldrich

Palladium(II) acetate

≥99.9% trace metals basis

Synonym: Pd(OAc)2

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Properties

Related Categories C-H Activation, Catalysis, Catalysis and Inorganic Chemistry, Catalysts, Chemical Synthesis,
InChI Key   YJVFFLUZDVXJQI-UHFFFAOYSA-L
assay   ≥99.9% trace metals basis
mp   216.3-223.7 °C (dec.)

Description

Frequently Asked Questions

Frequently Asked Questions are available for this Product.

Packaging

1, 5, 25, 100 g in glass bottle

Application

Application Guide for Palladium Catalyzed Cross-Coupling Reactions

Palladium(II) acetate was employed as a catalyst for the following reactions:
• Formation of allylic acetates. (eq. 1)
• Hydroselenation of triple bonds. (eq. 2)
• Heck arylation of alkenes. (eq. 3)
• Cyclocarbonylation. (eq. 4)
• Buchwald-Hartwig amination reaction. (eq. 5)
Pd(OAc)<SUB>2</SUB> catalyst

General description

Palladium(II) acetate is a homogenous oxidation catalyst. It participates in the activation of alkenic and aromatic compounds towards oxidative inter- and intramolecular nucleophilic reactions. Crystals of palladium(II) acetate have a trimeric structure, having symmetry D3h. Each of the palladium atoms in the crystals are joined to the other two by double acetate bridges. Microencapsulation of palladium(II) acetate in polyurea affords polyurea-encapsulated palladium(II) acetate. It is a versatile heterogeneous catalyst for various phosphine-free cross-coupling reactions. It participates as catalyst in the Heck coupling reaction of pthalides with different alkenes.

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Cross-Coupling Guide
Safety & Documentation

Safety Information

Symbol 
GHS05  GHS05
Signal word 
Danger
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
2
RTECS 
AJ1900000

Frequently Asked Questions

Which document(s) contains shelf-life or expiration date information for a given product?
If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis. These documents are located on the product detail page under Useful Links & Tools. Click on the following link to search for a Certificate of Analysis. Please click the following link to see the details on our Product Dating Information.
How do I get lot-specific information or a Certificate of Analysis?
A Certificate of Analysis is available by lot number and can be obtained through our Advanced Search Option: http://www.sigmaaldrich.com/catalog/AdvancedSearchPage.do
What reactions are Product 520764, Palladium (II) acetate, used in?
Palladium (II) acetate is used as a catalyst for a number of reactions, including:  Suzuki coupling reactions, (See ChemFiles 2.1 and ChemFiles 4.2) vinylation, (i.e. the Heck Reaction), rearrangement of acyclic dienes (i.e. the Cope Reaction).Papers that cite the use of this reagent are listed below. 1. B.M. Trost Tet. 33, 2615, (1977)2. R.F. Heck Acc. Chem. Res. 12, 146, (1979)3. Tet. 62, 9002, (2006)4. Org. Lett. 8, 3311, (2006) abstract5. Organometallic News 2, 52, (2002)
What is Product 520764, Palladium (II) acetate, soluble in?
Palladium acetate is not water-soluble; it is organic soluble. Although Sigma-Aldrich does not test solubility of 520764 directly, it is expected to be soluble in most common organic solvents, like chloroform, methylene chloride and acetone, according to the manufacturer.
When using are Product 520764, Palladium (II) acetate, what can I use to remove traces of palladium that this catalyst may leave behind?
We would recommend using a metallic scavenger like the QuadraPureTM products. Product numbers 655422 and 657662 are designed to scavenge palladium ions and are effective in both acidic and basic conditions. The resins are capable of removing metallic contamination to very low levels and are ideal for pharmaceutical or fine chemical processing. More information on these products and an application guide can be found at the link below. http://www.sigmaaldrich.com/Area_of_Interest/Chemistry/Drug_Discovery/Medicinal_Chemistry/Quadrapure.html
What is the difference between Product 520764, Palladium (II) acetate, and the palladium acetate in the form of a ChemDose® tablet?
The ChemDose® products offer a streamlined way to catalyze reactions. The catalyst is dispersed in an inert tablet matrix in specific millimolar and micromolar quantities. The tablets can decrease time spent on weighing/adding the catalyst to the reaction mixture. The tablets effectively give the same reaction yields with a controlled release of the catalyst. They are also extremely easy to remove after the reaction is complete. The inert tablet usually stays intact throughout the reaction. Product 684929 is the ChemDose® tablet that contains 2.0 µmol of palladium (II) acetate, while product#: 685593 is the 10µmol version. More information on these products can be found at the link below.  http://www.sigmaaldrich.com/Area_of_Interest/Chemistry/Chemical_Synthesis/Product_Highlights/ChemDose.html
What atmosphere is Product 520764, Palladium (II) acetate, packaged under?
This material is packaged under a layer of nitrogen to reduce the chance of moisture contamination.
How do I find price and availability?
There are several ways to find pricing and availability for our products.  Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers. 
What is the Department of Transportation shipping information for this product?
Transportation information can be found in Section 14 of the product's (M)SDS. To access the shipping information for this material, use the link on the product detail page for the product, or search here. 
My question is not addressed here, how can I contact Technical Service for assistance?
Use the option to the right to "Ask a Question" by email of a Technical Service Scientist.
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Protocols & Articles

Articles

Heck Reaction

The Heck reaction is the palladium catalyzed cross-coupling reaction between alkenes, and aryl or vinyl halides (or triflates) to afford substituted alkenes.1,2 It is a useful carbon–carbon bond form...
Keywords: Asymmetric synthesis, Cancer, Catalysis, Coupling reactions, Cross couplings, Heck Reaction, Herbicides, Ligands, Organic synthesis, Solvents

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Application Guide for Palladium Catalyzed Cross-Coupling Reactions

Palladium catalyzed cross-coupling reactions have revolutionized the way in which molecules are constructed. From the fields of organic synthesis and medicinal chemistry, to materials science and pol...
Keywords: Catalysis, Coupling reactions, Cross couplings, Materials Science, Medicinal chemistry, Organic synthesis, Polymer science, Type, transformation

Peer-Reviewed Papers
15

References

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