52409-22-0

Basic information

• Product Name: BIS(DIBENZYLIDENEACETONE)PALLADIUM
• Synonyms: PALLADIUM(0) BIS(DIBENZYLIDENEACETONE);PALLADIUM (0) BIS(DIBENZYLIDENEACETONE) SALT;PD(DBA)2;BIS(DIBENZYLIDENEACETONE) PALLADIUM(0);tris(dibenzylideneacetone)dipalladium(o)(pd2(dba)3);Tris(dibenzylideneacetone)dipalladium(0) [20% Pd];Bis(dibenzylideneacetone)dipalladium;Pd(dba)3
• CAS NO: 52409-22-0
• Molecular Formula: 3C₁₇H₁₄O*2Pd
• Molecular Weight: 575
• EINECS: 1312995-182-4
• Product Categories: Catalysts-Ligands
• Mol File: 52409-22-0.mol
• Article Data: 3

Chemical Properties

• Melting Point: 152-155 °C(lit.)
• Appearance: /
• Storage Temp.: Store at RT.
• Water Solubility: insoluble
• CAS DataBase Reference: BIS(DIBENZYLIDENEACETONE)PALLADIUM(CAS DataBase Reference)
• NIST Chemistry Reference: BIS(DIBENZYLIDENEACETONE)PALLADIUM(52409-22-0)
• EPA Substance Registry System: BIS(DIBENZYLIDENEACETONE)PALLADIUM(52409-22-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 52409-22-0(Hazardous Substances Data)

Usage

General Description

Bis(Dibenzylideneacetone)Palladium, also known as Pd(dba)2, is a coordination compound of palladium often used as a catalyst or precursor for catalysts in palladium-catalyzed reactions such as Suzuki reactions, Buchwald-Hartwig amination and various other organic transformations. It is generally yellowish-orange in color and insoluble in water but soluble in organic solvents. As it regards its structure, it features palladium in the oxidation state II, with two acetone-derived ligands, described as a relatively air-stable compound. Its safety and health effects have not been widely studied, but like other palladium compounds, it should be handled with precaution.

InChI:InChI=1/3C17H14O.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;;/b13-11+,14-12+;2*13-11-,14-12+;;

Upstream product

• 35225-79-7 dibenzylideneacetone 
• 3375-31-3 palladium diacetate 
• 21264-30-2 dichloro bis(acetonitrile) palladium(II) 
• 538-58-9 1,5-diphenyl-1,4-pentadiene-3-one 
• 32005-36-0 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 

Downstream Products

• 326817-95-2 [4-(5-Methyl-3-phenyl-isoxazol-4-yl)-pyrimidin-2-yl]-phenyl-amine 
• 404011-08-1 1-(2,6-dihydroxy-4-morpholin-4-yl-phenyl)-ethanone 
• 337536-06-8 1-[6-[(diphenylmethylene)amino]-4'-fluoro[1,1'-biphenyl]-3-yl]-2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanol 
• 192460-93-8 2-carbomethoxy-3-(4-bromophenyl)-8-oxabicyclo[3.2.1]-2-octene 
• 253191-94-5 4-(1-naphthalen-2-ylpiperidin-4-ylamino)benzoic acid tert-butyl ester 
• 280583-02-0 1-(2-chloro-4-morpholinobenzyl)-2-methyl-6-((4-methylbenzene)sulfonylcarbamoyl)benzimidazole 
• 639816-37-8 4-(5-formyl-2-thiophenyl)benzoic acid methyl ester 
• 773878-65-2 4-isopropyl-N-(6-piperazin-1-ylpyridin-3-yl)benzenesulfonamide 
• 1356681-60-1 9-{5-O-[bis(4-methoxyphenyl)(phenyl)methyl]-2-o-[4-(1,3-oxazol-2-yl)benzyl]-β-D-ribofuranosyl}-6-[2-(trimethylsilyl)ethoxy]-9H-purine 
• 69861-71-8 bis(tri-ortho-tolylphosphine)palladium⁽⁰⁾ 
• 1537904-50-9 [(DMOBD)Pd(bis(diphenylphosphino)ethane)]*CH₂Cl₂ 

Relevant articles and documents

Preparation method of high-purity tris(dibenzylideneacetone)dipalladium (0)

The invention discloses a preparation method of high-purity tris(dibenzylideneacetone)dipalladium (0). The method includes 1, in a nitrogen atmosphere, adding ligand dibenzylideneacetone, palladium dichloride and anhydrous sodium acetate to anhydrous ethanol that is in a stirring state to carry out a heating reaction, and performing filtering to obtain solid bis(dibenzylideneacetone)palladium (0); 2, in a nitrogen atmosphere, adding the solid bis(dibenzylideneacetone)palladium (0) obtained in the step 1 to acetone that is in a stirring state, washing a retained product after filtering, and drying the washed retained product to obtain the tris(dibenzylideneacetone)dipalladium (0). The preparation method has the advantages that the bis(dibenzylideneacetone)palladium (0) is prepared from the anhydrous ethanol, the dibenzylideneacetone, the palladium dichloride and the anhydrous sodium acetate at first, and then is treated by an acetone solution to obtain the tris(dibenzylideneacetone)dipalladium (0), and accordingly, the obtained tris(dibenzylideneacetone)dipalladium (0) has high purity.

Enantioselective Synthesis of Homoallylic Azides and Nitriles via Palladium-Catalyzed Decarboxylative Allylation

Azides and nitriles are important building blocks for the synthesis of nitrogen-containing bioactive compounds. The first example of enantioselective palladium-catalyzed decarboxylative allylation of α-azido and cyano β-ketoesters is reported. Indanone derivatives were obtained in 50-88% yield/77-97% ee and 46-98% yield/78-93% ee for azide and nitrile substituents, respectively. The required starting materials were synthesized in one step from ketoesters via electrophilic azidation and cyanation using benziodoxole hypervalent iodine reagents. The products could be easily converted into useful nitrogen-containing building blocks, such as triazoles, amides, or α- and β- amino ketones.