Bis(acetonitrile)dichloropalladium(II)

Bis(acetonitrile)dichloropalladium(II) Basic information
Reaction
Product Name:Bis(acetonitrile)dichloropalladium(II)
Synonyms:PALLADIUM(II) CHLORIDE-DIACETONITRILE COMPLEX;PALLADIUM-BIS-ACETONITRIL-DICHLORIDE;PALLADIUM DICHLOROBIS(ACETONITRILE);TRANS-DICHLOROBIS(ACETONITRILE)PALLADIUM;TRANS-BIS(ACETONITRILE)PALLADIUM(II) CHLORIDE;Bis(acetonitriL;e)dichL;PALLADIUM(2+) ION BIS(ACETONITRILE) DICHLORIDE
CAS:14592-56-4
MF:C4H6Cl2N2Pd
MW:259.43
EINECS:238-637-3
Product Categories:Pd;organometallic complexes;Metal Compounds;Pd (Palladium) Compounds;Synthetic Organic Chemistry;Transition Metal Compounds;Catalysts for Organic Synthesis;Classes of Metal Compounds;Homogeneous Catalysts;Metal Complexes
Mol File:14592-56-4.mol
Bis(acetonitrile)dichloropalladium(II) Structure
Bis(acetonitrile)dichloropalladium(II) Chemical Properties
Melting point 300 °C
storage temp. Inert atmosphere,Room Temperature
solubility Soluble in acetonitrile, acetone, chloroform
form Fine Crystalline Powder
color Orange to rust-brown
Water Solubility insoluble
CAS DataBase Reference14592-56-4(CAS DataBase Reference)
Safety Information
Hazard Codes T,Xn
Risk Statements 23/24/25-36/37/38-20/21/22
Safety Statements 16-27-36/37-45-36-26
RIDADR UN 3077 9/PG 3
WGK Germany 3
TSCA No
HazardClass 6.1
PackingGroup III
HS Code 28439090
MSDS Information
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Bis(acetonitrile)dichloropalladium(II) English
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Bis(acetonitrile)dichloropalladium(II) Usage And Synthesis
Reaction
  1. Catalyst for the cyclization of δ-acetylenic carboxylic acids to butenolides.
  2. Catalyst for the aza-Michael reaction of carbamates with enones.
  3. Catalyst for the rearrangement of allylic imidates to allylic amides.
  4. Catalyst for the Nazarov cyclization of α-alkoxy dienones.
  5. Catalyst for the diamination of conjugated dienes.
  6. Three component Michael addition, cyclization, cross-coupling reaction.
  7. C-H activation of indoles.
  8. Catalyst used for the direct C-H arylation of isoxazoles at the 5 position.
Reactions of 14592-56-4_1
Reactions of 14592-56-4_2
Chemical PropertiesLight yellow to Brown powder to crystaline.
Physical propertiesBis(acetonitrile)dichloropalladium(II) is a yellow-brown solid that is soluble in organic solvents. It is a reagent and a catalyst for reactions that require soluble Pd(II).The compound is similar to bis(benzonitrile)palladium dichloride. 
Usessuzuki reaction
UsesIt is used as a catalyst in an ether-directed aza-Claisen rearrangement. Also used in cyclization and cross-coupling reactions. It is applied for olefin isomerization, preparation of acetals and hemiacetal esters.
UsesCatalyst used in an ether-directed aza-Claisen rearrangement.
PreparationBis(acetonitrile)palladium dichloride is prepared by reacting two acetonitrile ligands and palladium(II) chloride.
ApplicationSynthesis of Oxindoles
Synthesis of Oxindoles.gif
To a dried screw-cap vial is added anilide (0.3 mmol), AgOCOCF3 (132.5 mg, 0.6 mmol), Bis(acetonitrile)dichloropalladium(II) (3.5 mg, 0.015 mmol) and chlorobenzene. The reaction mixture is stirred at 100-120 °C for 3-12 h in a pre-heated oil bath. After cooling to room temperature, the reaction is diluted with EtOAc and filtered with a glass filter. The filtrate is washed with 5% aqueous NaHCO3 and brine. The extract is dried over MgSO4 and concentrated in vacuo. The crude is purified by preparative TLC.
General DescriptionThis product has been enhanced for catalytic efficiency.
Bis(acetonitrile)dichloropalladium(II) Preparation Products And Raw materials
Raw materialsDichloromethane-->Acetonitrile-->Palladium chloride
Preparation ProductsBIS(DI-TERT-BUTYL(4-DIMETHYLAMINOPHENYL)PHOSPHINE)DICHLOROPALLADIUM
N,N'-Dimethyl-1,2-ethanediamine BIS(PENTAMETHYLCYCLOPENTADIENYL)MANGANESE BIS(PENTAMETHYLCYCLOPENTADIENYL)RUTHENIUM Tetrakis(triphenylphosphine)platinum Allylpalladium(II) Chloride Dimer BIS(PENTAMETHYLCYCLOPENTADIENYL)NICKEL Bis(tri-tert-butylphosphine)palladium(0) Bis(pentamethylcyclopentadienyl)iron(II) BIS(ETHYLCYCLOPENTADIENYL)NICKEL BIS(I-PROPYLCYCLOPENTADIENYL)TITANIUM DICHLORIDE BIS(PENTAMETHYLCYCLOPENTADIENYL)MAGNESIUM BIS(I-PROPYLCYCLOPENTADIENYL)MANGANESE BIS(N-PROPYLCYCLOPENTADIENYL)MAGNESIUM Diamminedichloropalladium Bis(benzonitrile)palladium chloride Palladium Palladium chloride Bis(acetonitrile)dichloropalladium(II)

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