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205869

Sigma-Aldrich

Palladium(II) acetate

reagent grade, 98%

Synonym(s):

Pd(OAc)2, [Pd(OAc)2]3

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About This Item

Linear Formula:
Pd(OCOCH3)2
CAS Number:
3375-31-3
Molecular Weight:
224.51
Beilstein/REAXYS Number:
6086766
EC Number:
222-164-4
MDL number:
MFCD00012453
UNSPSC Code:
12161600
PubChem Substance ID:
24852356
NACRES:
NA.22

grade

reagent grade

Quality Level

200

assay

98%

form

powder

reaction suitability

core: palladium
reaction type: Buchwald-Hartwig Cross Coupling Reaction
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

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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General description

[Pd(OAc)2]3 is a palladium coordination complex and a heterogenous metal catalyst that is widely used in organic synthesis such as transmetalation, insertion, oxidative addition, direct homocoupling of aryl halides, Buchwald-Hartwig reaction of C-N bond formation, reduction of alkynes, and reductive elimination reactions. It is also employed as a starting material for the synthesis of other Pd(II) compounds as well as for the preparation of active palladium catalysts for Suzuki-Miyaura cross-coupling and C-H functionalization reactions.

Application

Application Guide for Palladium Catalyzed Cross-Coupling Reactions
[Pd(OAc)2]3 can be used as a:
  • Catalyst for the regioselective anti-hydrochlorination of the terminal and internal alkynes.
  • Precursor to prepare a heterogeneous palladium complex catalyst for the Heck-Coupling reaction and Sonogashira cross-coupling reaction.

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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

Certificates of Analysis (COA)

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Synthesis and characterization of bis (amine) palladium (ii) carboxylate complexes as precursors of palladium nanoparticles
Zakrzewska J and Uznanski P
Dalton Transactions, 50, 6933-6948 (2021)
Mesoporous Palladium N, N?-Bis (3-Allylsalicylidene) o-Phenylenediamine-Methyl Acrylate Resins as Heterogeneous Catalysts for the Heck Coupling Reaction
Mella C, et al.
MATERIALS, 12, 2612-2612 (2019)
Polystyrene-Anchored Palladium (II) Schiff Base Complex: A Reusable Catalyst for Phosphine-Free and Copper-Free Sonogashira Cross-Coupling Reaction in Aqueous Medium
Islam M, et al.
Synthetic Communications, 41, 2583-2593 (2011)
Palladium (II) Acetate [Pd (OAc)2]: A Versatile Catalyst
Vats R
Synlett, 2006, 329-330 (2006)
Palladium (II)-catalyzed directed anti-hydrochlorination of unactivated alkynes with HCl
Derosa J, et al.
Journal of the American Chemical Society, 139, 5183-5193 (2017)
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