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520764

Sigma-Aldrich

[Pd(OAc)2]3

≥99.9% trace metals basis

Sinónimos:

Pd(OAc)2

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1 G
$117.00
5 G
$482.00
25 G
$2,050.00
100 G
$7,700.00

$117.00

Disponible para envío el23 de abril de 2025Detalles

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1 G
$117.00
5 G
$482.00
25 G
$2,050.00
100 G
$7,700.00

About This Item

Fórmula lineal:
Pd(OCOCH3)2
Número de CAS:
3375-31-3
Peso molecular:
224.51
Beilstein:
6086766
Número CE:
222-164-4
Número MDL:
MFCD00012453
Código UNSPSC:
12161600
ID de la sustancia en PubChem:
24874166
NACRES:
NA.22

$117.00

Disponible para envío el23 de abril de 2025Detalles

Solicitar un pedido a granel

Nivel de calidad

200

Ensayo

≥99.9% trace metals basis

idoneidad de la reacción

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

mp

216.3-223.7 °C (dec.)

cadena SMILES

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

Clave InChI

YJVFFLUZDVXJQI-UHFFFAOYSA-L

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Descripción general

El acetato de paladio (II) es un catalizador homogéneo de la oxidación. Participa en la activación de los compuestos alquénicos y aromáticos hacia reacciones nucleófilas oxidativas intermoleculares e intramoleculares.[1] Los cristales de acetato de paladio (II) tienen una estructura trimérica con simetría D3h. Cada uno de los átomos de paladio de los cristales está unido a los otros dos mediante puentes dobles de acetato. [2] La microencapsulación del acetato de paladio (II) en poliurea produce acetato de paladio (II) encapsulado en poliurea. Es un versátil catalizador heterogéneo para varias reacciones de acoplamiento cruzado sin fosfina.[3] Participa como catalizador en la reacción de acoplamiento de Heck de ftalidas con diferentes alquenos.[4]

Aplicación

Guía de aplicaciones para las reacciones de acoplamiento transversal catalizadas por paladio
El acetato de paladio(II) se empleó como catalizador para las siguientes reacciones:
  • Formación de acetatos alílicos.[5] (eq. 1)
  • Hidroselenación de enlaces triples[6] (eq. 2)
  • Arilación de Heck de alquenos.[7] (eq. 3)
  • Ciclocarbonilación.[8] (eq. 4)
  • Reacción de aminación de Buchwald-Hartwig.[9] (eq. 5)
Pd(OAc)<sub>2</sub> catalyst
Para usos a pequeña escala y de alto rendimiento, el producto también está disponible como ChemBeads (924377)

Producto relacionado

Referencia del producto
Descripción
Precios

922889

DMPDAB-Pd-MAH, ≥95%

Palabra de señalización

Danger

Frases de peligro

H317,H318,H410

Clasificaciones de peligro

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

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 2

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

dust mask type N95 (US), Eyeshields, Gloves

Elija entre una de las versiones más recientes:

Certificados de análisis (COA)

Lot/Batch Number
MKCX3438
MKCX2188
0000279356
MKCW6413
MKCV5635

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Encuentre la documentación para los productos que ha comprado recientemente en la Biblioteca de documentos.

Visite la Librería de documentos

A Facile Synthesis of Novel Cyclic Esters of γ-Keto Acid Derivatives by Heck Coupling Reaction.
ShashiKumar ND, et al.
Journal of Heterocyclic Chemistry, 51(S1), E354-E357 (2014)
Wolfe, J. P.; Buchwald, S. L.
The Journal of Organic Chemistry, 62, 1264-1264 (1997)
The crystal structure of Trimeric palladium (II) acetate.
Skapski AC and Smart ML.
Journal of the Chemical Society. Chemical Communications, 11, 658b-6659 (1970)
Palladium (II) Acetate
Grennberg H, et al.
e-EROS Encyclopedia of Reagents for Organic Synthesis. (2015)
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)
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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

      Helpful?

  3. 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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  4. 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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  5. 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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  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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