Skip to Content
Merck
All Photos(6)

Key Documents

View All Documentation

227994

Sigma-Aldrich

Bis(dibenzylideneacetone)palladium(0)

Synonym(s):

Palladium(0) bis(dibenzylideneacetone), Pd(dba)2

Sign Into View Organizational & Contract Pricing

Select a Size

500 MG
CHF 63.90
2 G
CHF 208.00
5 G
CHF 236.00
50 G
CHF 1’950.00

CHF 63.90

Estimated to ship on22 March 2025

Request a Bulk Order
All Photos(6)

Select a Size

Change View
500 MG
CHF 63.90
2 G
CHF 208.00
5 G
CHF 236.00
50 G
CHF 1’950.00

About This Item

Linear Formula:
(C6H5CH=CHCOCH=CHC6H5)2Pd
CAS Number:
32005-36-0
Molecular Weight:
575.00
MDL number:
MFCD00051942
UNSPSC Code:
12161600
PubChem Substance ID:
24853668
NACRES:
NA.22

CHF 63.90

Estimated to ship on22 March 2025

Request a Bulk Order

form

powder

Quality Level

100

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

SMILES string

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

InChI

1S/2C17H14O.Pd/c2*18-17(13-11-15-7-3-1-4-8-15)14-12-16-9-5-2-6-10-16;/h2*1-14H;/b2*13-11+,14-12+;

InChI key

UKSZBOKPHAQOMP-SVLSSHOZSA-N

General description

Bis(dibenzylideneacetone)palladium(0) (Pd(dba)2) is an air stable Pd0 complex. It is a reagent for the synthesis of allylic substituted cyclopentadienes.[1] It is a homogeneous catalyst.[2][3] It catalyzes the alkylation of allyl acetates by various nucleophiles under mild conditions.[4]

Application

Application Guide for Palladium Catalyzed Cross-Coupling Reactions
Bis(dibenzylideneacetone)palladium(0) (Pd(dba)2) was employed as catalyst in the following studies:
  • Synthesis of isomeric 2-aryl-2,5-dihydrofurans, via Heck coupling of aryl bromides with alkenes using neopentyl phosphine ligands.[5]
  • Heck reaction of benzyl trifluoroacetate and 2,3-dihydrofuran phosphoramidite ligand.[6]
  • Allylation of stabilized anions.[7]
  • Cross coupling of allyl, alkenyl and aryl halides with organostannanes.[7]
  • Cross coupling of vinyl halides with alkenyl zinc species.[7]
  • Carbonylation of alkenyl and aryl halides.[7]
  • Employed with cyclic thiourea ligands in an efficient aerobic oxidation of alcohols to aldehydes and ketones.[8]

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKCW4974
MKCW0564
MKCV6896
MKCT9164
MKCV3293

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Tetrahedron Letters, 22, 1399-1399 (1981)
Cuerva, J. M.; Gomez-Bengoa, E.; et al
The Journal of Organic Chemistry, 62, 7540-7540 (1997)
Xiaoxiang Liu et al.
Journal of the American Chemical Society, 126(16), 5182-5191 (2004-04-22)
A general procedure for the palladium-catalyzed arylation of trimethylsilyl enolates of esters and imides is reported. In the presence of ZnF2 or Zn(O-t-Bu)2 as an additive, the trimethylsilyl enolates of esters, including those bearing alpha-alkoxy derivatives, underwent arylation in high
Tetrahedron Letters, 21, 4437-4437 (1980)
Tetrahedron Letters, 25, 4379-4379 (1984)
View All Related Papers

Questions

1–2 of 2 Questions  

  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      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/449/386/product-dating-information-mk.pdf

      Helpful?

  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    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

      Helpful?

Reviews

No rating value

Active Filters

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service