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520764

Sigma-Aldrich

[Pd(OAc)2]3

≥99.9% trace metals basis

Sinonimo/i:

Pd(OAc)2

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1 G
CHF 101.00
5 G
CHF 417.00
25 G
CHF 1’770.00
100 G
CHF 6’660.00

CHF 101.00


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Cambia visualizzazione
1 G
CHF 101.00
5 G
CHF 417.00
25 G
CHF 1’770.00
100 G
CHF 6’660.00

About This Item

Formula condensata:
Pd(OCOCH3)2
Numero CAS:
Peso molecolare:
224.51
Beilstein:
6086766
Numero CE:
Numero MDL:
Codice UNSPSC:
12161600
ID PubChem:
NACRES:
NA.22

CHF 101.00


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Livello qualitativo

Saggio

≥99.9% trace metals basis

Impiego in reazioni chimiche

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
reaction type: C-H Activation

Punto di fusione

216.3-223.7 °C (dec.)

Stringa SMILE

CC(O[Pd]OC(C)=O)=O

InChI

1S/2C2H4O2.Pd/c2*1-2(3)4;/h2*1H3,(H,3,4);/q;;+2/p-2
YJVFFLUZDVXJQI-UHFFFAOYSA-L

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Descrizione generale

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.[1] 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.[2] 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.[3] It participates as catalyst in the Heck coupling reaction of pthalides with different alkenes.[4]

Applicazioni

Palladium(II) acetate was employed as a catalyst for the following reactions:
  • Formation of allylic acetates.[5] (eq. 1)
  • Hydroselenation of triple bonds.[6] (eq. 2)
  • Heck arylation of alkenes.[7] (eq. 3)
  • Cyclocarbonylation.[8] (eq. 4)
  • Buchwald-Hartwig amination reaction.[9] (eq. 5)
Pd(OAc)<sub>2</sub> catalyst
For small scale and high throughput uses, product is also available as ChemBeads (924377)

Prodotti correlati

N° Catalogo
Descrizione
Determinazione del prezzo

Avvertenze

Danger

Indicazioni di pericolo

Classi di pericolo

Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1 - Skin Sens. 1A

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 2

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

dust mask type N95 (US), Eyeshields, Gloves


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A Facile Synthesis of Novel Cyclic Esters of γ-Keto Acid Derivatives by Heck Coupling Reaction.
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Journal of Heterocyclic Chemistry, 51(S1), E354-E357 (2014)
Palladium(II)-catalyzed C-H bond arylation of electron-deficient arenes at room temperature.
Matthew J Tredwell et al.
Angewandte Chemie (International ed. in English), 50(5), 1076-1079 (2011-01-27)
Palladium (II) Acetate
Grennberg H, et al.
e-EROS Encyclopedia of Reagents for Organic Synthesis. (2015)
The crystal structure of Trimeric palladium (II) acetate.
Skapski AC and Smart ML.
Journal of the Chemical Society. Chemical Communications, 11, 658b-6659 (1970)
Brunner, M.; Alper, H
The Journal of Organic Chemistry, 62, 7565-7565 (1997)

Questions

1–8 of 8 Questions  
  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  3. What is Product 520764, Palladium (II) acetate, soluble in?

    1 answer
    1. 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.

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  4. What reactions are Product 520764, Palladium (II) acetate, used in?

    1 answer
    1. 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)

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  5. What atmosphere is Product 520764, Palladium (II) acetate, packaged under?

    1 answer
    1. This material is packaged under a layer of nitrogen to reduce the chance of moisture contamination.

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  6. When using are Product 520764, Palladium (II) acetate, what can I use to remove traces of palladium that this catalyst may leave behind?

    1 answer
    1. 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.

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  7. What is the difference between Product 520764, Palladium (II) acetate, and the palladium acetate in the form of a ChemDose® tablet?

    1 answer
    1. 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.

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  8. What is the Department of Transportation shipping information for this product?

    1 answer
    1. 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.

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