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520764

Sigma-Aldrich

[Pd(OAc)2]3

≥99.9% trace metals basis

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Synonym(s):
Palladium(II) acetate, Pd(OAc)2
Linear Formula:
Pd(OCOCH3)2
CAS Number:
Molecular Weight:
224.51
Beilstein/REAXYS Number:
6086766
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

≥99.9% trace metals basis

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
reaction type: C-H Activation

mp

216.3-223.7 °C (dec.)

SMILES string

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

InChI key

YJVFFLUZDVXJQI-UHFFFAOYSA-L

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1 of 4

This Item
379875205869683124
[Pd(OAc)2]3 ≥99.9% trace metals basis

520764

[Pd(OAc)2]3

[Pd(OAc)2]3 99.98% trace metals basis

379875

[Pd(OAc)2]3

[Pd(OAc)2]3 reagent grade, 98%

205869

[Pd(OAc)2]3

[Pd(OAc)2]3 Umicore, 46.6-49.5% palladium (Pd) basis

683124

[Pd(OAc)2]3

assay

≥99.9% trace metals basis

assay

99.98% trace metals basis

assay

98%

assay

-

Quality Level

200

Quality Level

-

Quality Level

200

Quality Level

-

mp

216.3-223.7 °C (dec.)

mp

216.3-223.7 °C (dec.)

mp

216.3-223.7 °C (dec.)

mp

216.3-223.7 °C (dec.)

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.

Application

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
For small scale and high throughput uses, product is also available as ChemBeads (924377)

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Danger

Hazard Classifications

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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.
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)
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)
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)

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