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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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCR0213
MKCP7970
MKCP4128
MKCN9547
MKCN2889

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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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Transition-Metal Catalysts

A variety of transition-metal catalysts for the Suzuki coupling reaction are now available in our catalog. The majority of these catalysts are palladium- and nickelbased, typically utilizing phosphine-derived ligands.

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