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Bis(dibenzylideneacetone)palladium

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Bis(dibenzylideneacetone)palladium Basic information

Product Name:
Bis(dibenzylideneacetone)palladium
Synonyms:
  • BIS(DIBENZYLIDENEACETONE)PALLADIUM
  • BIS(DIBENZYLIDENEACETONE) PALLADIUM(0)
  • PALLADIUM (0) BIS(DIBENZYLIDENEACETONE) SALT
  • PALLADIUM(0) BIS(DIBENZYLIDENEACETONE)
  • PD(DBA)2
  • Bis(dibenzylideneacetone)palladium(0) Pd(dba)2Pd2(dba)3dba
  • BIS(DIBENZYLIDENEACETONE)PALLADIUM(O)
  • Bis(dibenzylideneacetone)palladium(0) Pd(dba)2Pd2(dba)3ba
CAS:
32005-36-0
MF:
C34H20O2Pd
MW:
566.95
EINECS:
608-691-6
Product Categories:
  • chemical reaction,pharm,electronic,materials
  • organometallic complex
  • Catalysts for Organic Synthesis
  • Classes of Metal Compounds
  • Catalysts-Ligands
  • Pd
  • Homogeneous Catalysts
  • Metal Complexes
  • Pd (Palladium) Compounds
  • Synthetic Organic Chemistry
  • Transition Metal Compounds
Mol File:
32005-36-0.mol
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Bis(dibenzylideneacetone)palladium Chemical Properties

Melting point:
150°C
storage temp. 
under inert gas (nitrogen or Argon) at 2–8 °C
solubility 
Chloroform (Slightly)
form 
Fine Powder
color 
Red-brown to black
Water Solubility 
insoluble
Sensitive 
Air & Moisture Sensitive
Stability:
Hygroscopic
InChI
InChI=1S/2C17H10O.Pd/c2*18-17(13-11-15-7-3-1-4-8-15)14-12-16-9-5-2-6-10-16;/h2*1-10H;
InChIKey
WTAPZWXVSZMMDG-JZOPPWQGSA-N
SMILES
O=C1C2=C(C3C=CC=CC=3)[Pd]34562(C(C2C=CC=CC=2)=C3C(=O)C4=C5C2C=CC=CC=2)C(C2C=CC=CC=2)=C16
CAS DataBase Reference
32005-36-0(CAS DataBase Reference)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/38
Safety Statements 
22-24/25-37/39-26
WGK Germany 
3
TSCA 
No
HS Code 
28439000

MSDS

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Bis(dibenzylideneacetone)palladium Usage And Synthesis

Reaction

  1. Palladium-catalyzed acylation of unsaturated halides by anions of enol ethers.
  2. Asymmmetric Allylation reactions.
  3. Intramolecular reactions with alkenes.
  4. Carbonylation reactions.
  5. Cross Coupling reactions.


Chemical Properties

purple brown

Uses

Hydrogenation, isomerization, carbonylation, oxidation, C-C bond formation.Bis(dibenzylideneacetone)palladium(0) is used as a reagent for the preparation of allylic substituted cyclopentadienes. It acts as a homogeneous catalyst as well as in the alkylation of allyl acetates by various nucleophiles. Further, it is used in Suzuki reaction.

Uses

Application Guide for Palladium Catalyzed Cross-Coupling Reactions

Application

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.
Heck reaction of benzyl trifluoroacetate and 2,3-dihydrofuran phosphoramidite ligand.
Allylation of stabilized anions.Cross coupling of allyl, alkenyl and aryl halides with organostannanes.
Cross coupling of vinyl halides with alkenyl zinc species.Carbonylation of alkenyl and aryl halides.
Employed with cyclic thiourea ligands in an efficient aerobic oxidation of alcohols to aldehydes and ketones.

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. It is a homogeneous catalyst. It catalyzes the alkylation of allyl acetates by various nucleophiles under mild conditions.

Synthesis

Bis(dibenzylideneacetone)palladium(0) was prepared by reduction of PdCl2 with methanol in the presence of sodium acetate and dibenzylideneacetone, as dark-violet pre-cipitate with mp 152°C (150°C ). 

Bis(dibenzylideneacetone)palladium Preparation Products And Raw materials

Raw materials

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