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205869

Sigma-Aldrich

[Pd(OAc)2]3

reagent grade, 98%

Synonym(s):

Palladium(II) acetate, Pd(OAc)2

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About This Item

Linear Formula:
Pd(OCOCH3)2
CAS Number:
3375-31-3
Molecular Weight:
224.51
Beilstein:
6086766
EC Number:
222-164-4
MDL number:
MFCD00012453
UNSPSC Code:
12352300
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.

related product

Product No.
Description
Pricing

Signal Word

Danger

Hazard Statements

H317 - H318 - H410

Hazard Classifications

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Mark McLaughlin et al.
Organic letters, 8(15), 3311-3314 (2006-07-14)
[Structure: see text] An efficient regioselective method for the preparation of structurally diverse imidazopyridinones and benzoimidazolones starting from readily available and economical starting materials is described. High-yielding reductive alkylation of electron-deficient o-haloarylamines followed by treatment with inexpensive N-chlorosulfonyl isocyanate afforded
Wolfe, J. P.; Buchwald, S. L.
The Journal of Organic Chemistry, 62, 1264-1264 (1997)
Mark S Chen et al.
Journal of the American Chemical Society, 126(5), 1346-1347 (2004-02-05)
Sulfoxide ligation to Pd(II) salts is shown to selectively promote C-H oxidation versus Wacker oxidation chemistry and to control the regioselectivity in the C-H oxidation products. A catalytic method for the direct C-H oxidation of monosubstituted olefins to linear (E)-allylic
Ikuyo Kamiya et al.
The Journal of organic chemistry, 70(2), 696-698 (2005-01-18)
A highly regioselective hydroselenation of terminal alkynes with benzeneselenol can be achieved by the combination of palladium acetate and pyridine, providing the corresponding terminal alkenes, (i.e., 2-phenylseleno-1-alkenes) as a sole product. In this hydroselenation, pyridine may act as a suitable
Brunner, M.; Alper, H
The Journal of Organic Chemistry, 62, 7565-7565 (1997)
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