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Sigma-Aldrich

Palladium(II) acetylacetonate

99%

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Synonym(s):
Palladium(II) 2,4-pentanedionate, Pd(acac)2
Linear Formula:
Pd(C5H7O2)2
CAS Number:
14024-61-4
Molecular Weight:
304.64
Beilstein:
4136188
EC Number:
237-859-8
MDL number:
MFCD00000025
PubChem Substance ID:
24852227
NACRES:
NA.23

Quality Level

100

Assay

99%

form

powder

reaction suitability

core: aluminum
reagent type: catalyst

mp

200-251 °C (dec.)

SMILES string

CC(=O)\C=C(\C)O[Pd]O\C(C)=C/C(C)=O

InChI

1S/2C5H8O2.Pd/c2*1-4(6)3-5(2)7;/h2*3,6H,1-2H3;/q;;+2/p-2/b2*4-3-;

InChI key

JKDRQYIYVJVOPF-FDGPNNRMSA-L

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General description

Palladium(II) acetylacetonate (Pd(acac)2) is a metal-organic complex. Sublimation of Pd(acac)2 has been investigated by thermogravimetry and XRD. The temperature range for the sublimation of Pd(acac)2, without undergoing thermal decomposition, was determined to be 100-160°C in the presence of inert gas helium.

Application

Application Guide for Palladium Catalyzed Cross-Coupling Reactions
Palladium(II) acetylacetonate (Pd(acac)2) was used in the following studies:
  • Typical high-temperature organic solution phase protocol for the preparation of monodisperse CuPd alloy nanoparticles (NPs).
  • Preparation of [(NHC)Pd(acac)L] (where L=Me, NHC = N-heterocyclic carbene) complexes. These complexes efficiently catalyze the Heck reaction of activated aryl bromides.
  • As catalyst in the decarboxylative cross-coupling of arylcarboxylic acids with aryl halides.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H319

Hazard Classifications

Eye Irrit. 2

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

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Nicolas Marion et al.
Accounts of chemical research, 41(11), 1440-1449 (2008-09-09)
Metal-catalyzed cross-coupling reactions, notably those permitting C-C bond formation, have witnessed a meteoritic development and are now routinely employed as a powerful synthetic tool both in academia and in industry. In this context, palladium is arguably the most studied transition
Sublimation and deposition behaviour of palladium (II) acetylacetonate.
Cominos V and Gavriilidis A.
The European Physical Journal - Applied Physics, 15(01), 23-33 (2001)
Lukas J Goossen et al.
Journal of the American Chemical Society, 129(15), 4824-4833 (2007-03-23)
A new strategy for the regiospecific construction of unsymmetrical biaryls is presented, in which easily available salts of carboxylic acids are decarboxylated in situ to give arylmetal species that serve as the nucleophilic component in a catalytic cross-coupling reaction with
Sümeyra Diyarbakir et al.
ACS applied materials & interfaces, 7(5), 3199-3206 (2015-01-17)
Monodisperse CuPd alloy nanoparticles (NPs) were prepared by using a typical high-temperature organic solution phase protocol comprising the coreduction of copper(II) acetylacetonate and palladium(II) acetylacetonate by morpholine-borane complex in oleylamine and 1-octadecene solution at 80 °C. The presented synthesis protocol
Paul Chatelain et al.
Angewandte Chemie (International ed. in English), 58(42), 14959-14963 (2019-08-24)
Ideal organic syntheses involve the rapid construction of C-C bonds, with minimal use of functional group interconversions. The Suzuki-Miyaura cross-coupling (SMC) is a powerful way to form biaryl linkages, but the relatively similar reactivity of electrophilic partners makes iterative syntheses

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