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328774

Tris(dibenzylideneacetone)dipalladium(0)

97%, powder

Synonym(s):

Pd2dba3, Pd2(dba)3

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500 mg

Available to ship TODAYfromMILWAUKEE

$44.70
1 g

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$73.50
5 g

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$275.00
25 g

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$1,040.00
50 g

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$1,950.00
100 g

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$3,500.00
500 g

Estimated to ship onApril 20, 2026fromMILWAUKEE

$15,710.00

About This Item

Linear Formula:
(C6H5CH=CHCOCH=CHC6H5)3Pd2
CAS Number:
Molecular Weight:
915.72
UNSPSC Code:
12161600
PubChem Substance ID:
NACRES:
NA.22
MDL number:

$44.70


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Product Name

Tris(dibenzylideneacetone)dipalladium(0), 97%

Quality Level

assay

97%

form

powder

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

mp

152-155 °C (lit.)

SMILES string

[Pd].[Pd].O=C(\C=C\c1ccccc1)/C=C/c2ccccc2.O=C(\C=C\c3ccccc3)/C=C/c4ccccc4.O=C(\C=C\c5ccccc5)/C=C/c6ccccc6

InChI

1S/3C17H14O.2Pd/c3*18-17(13-11-15-7-3-1-4-8-15)14-12-16-9-5-2-6-10-16;;/h3*1-14H;;/b3*13-11+,14-12+;;

InChI key

CYPYTURSJDMMMP-WVCUSYJESA-N

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This Item
919772683345227994
reaction suitability

core: palladium, reaction type: Cross Couplings, reaction type: Hiyama Coupling, reaction type: Sonogashira Coupling, reaction type: Suzuki-Miyaura Coupling, reaction type: Heck Reaction, reaction type: Stille Coupling, reaction type: Negishi Coupling, reaction type: Buchwald-Hartwig Cross Coupling Reaction, reagent type: catalyst

reaction suitability

-

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 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

form

powder

form

solid

form

powder

form

powder

assay

97%

assay

-

assay

-

assay

-

Quality Level

200

Quality Level

100

Quality Level

200

Quality Level

100

mp

152-155 °C (lit.)

mp

-

mp

152-155 °C (lit.)

mp

-

General description

Tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3) is a versatile compound widely used as a Pd(0) source in various Pd-mediated transformations.[1] Pd2(dba)3 is known for its high reactivity and ability to facilitate oxidative addition reactions. It is prepared by reacting palladium salts with dibenzylideneacetone ligands. It acts as a catalyst for several reactions including Suzuki cross-coupling, Heck coupling, arylation, Buchwald-Hartwig amination, and fluorination. It is often used in catalytic amounts and has been shown to be effective in promoting coupling reactions between aryl halides and boronic acids.

For small scale and high throughput uses, product is also available as ChemBeads (919772)

Application

    Application Guide for Palladium Catalyzed Cross-Coupling Reactions

    Reactant involved in:

    • Synthesis of azepanes[2]
    • Synthesis of nanosized palladium phosphides upon interaction with white phosphorous
    • Preparation of palladium triphenylphosphine carbonyl cluster complexes
    • Precursor for synthesis of functionalized multiwalled carbon nanotube-palladium complexes used as catalysts for Heck coupling reactions
    • Selective carbon-sulfur bond formation via addition of S-S and S-H bonds to alkynes


    Catalyst for:

    • Suzuki cross-coupling reactions
    • PCN- and PCS-pincer palladium complex catalyzed tandem allylation
    • Catalyst for Suzuki coupling of aryl chlorides (eq. 1)
    • Catalyst for Heck coupling of aryl chlorides (eq. 2)
    • Catalyst for arylation of ketones (eq. 3)
    • Catalyst for Buchwald-Hartwig amination of aryl halides (eq. 4)
    • Catalyst for fluorination of allylic chlorides[3] (eq. 5)
    • Catalyst for β-arylation of carboxylic esters[4] (eq. 6)
    • Catalyst for carbonylation of 1,1-dichloro-1-alkenes[5] (eq. 7)
    • Catalyst for conversion of aryl and vinyl triflates to aryl and vinyl halides[6] (eq. 8)
    • Pd source for enantioselective Tsuji Allylations

pictograms

Exclamation markEnvironment

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Warning

hcodes

Hazard Classifications

Aquatic Chronic 2 - Skin Sens. 1

Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Catalysts for Suzuki?Miyaura Coupling Processes:? Scope and Studies of the Effect of Ligand Structure
Timothy E. Barder, Shawn D. Walker, Joseph R. Martinelli, and Stephen L. Buchwald
Journal of the American Chemical Society, 127(13), 4685?4696-4685?4696 (2005)
The Reaction Mechanism of the Enantioselective Tsuji Allylation: Inner-Sphere and Outer-Sphere Pathways, Internal Rearrangements, and Asymmetric C?C Bond Formation
John A. Keith, Douglas C. Behenna, et al.
Journal of the American Chemical Society, 134(46) , 19050?19060-19050?19060 (2012)
European Journal of Organic Chemistry, 10, 2214-2222 (2004)
Tetrahedron Letters, 33, 4859-4859 (1992)
Crystal and molecular structure of tris (dibenzylideneacetone) dipalladium (0).
Pierpont CG and Mazza MC
Inorganic Chemistry, 13(8), 1891-1895 (1974)

Articles

JosiPhos CyPF-tBu and palladium give catalyst for alkoxylation of activated heteroaryl halides with primary, secondary, and tertiary alcohols

Related Content

Global Trade Item Number

SKUGTIN
328774-500MG04061826717790
328774-1G04061826717776
328774-100G04061833546635
328774-50G04061826717806
328774-500G04061833498965
328774-25G04061826717783
328774-5G04061826717813

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      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

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    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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