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Tris(dibenzylideneacetone)dipalladium

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Tris(dibenzylideneacetone)dipalladium Basic information
Description Uses Reactions References
Product Name:Tris(dibenzylideneacetone)dipalladium
Synonyms:Bis(dibenzylideneacetone)palladium(0)~Pd_2(dba)_3;Tris(dibenzylidenaceTone) dipalladium (O);Tris(dibezylideneacetone)dipalladium;Palladium, tris.mu.-(1,2-.eta.:4,5-.eta.)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-onedi-;Tris(dibenzylidenaceton)dipalladium;TRIS(BIBENZYLIDENEACETONE) DIPALLADIUM;Tris(dibenzylideneacetone)dipalladium(0), Pd 21.5% min;Tris(dibenzylideneacetone)dipalladium(0), Pd content 22-24%
CAS:51364-51-3
MF:C51H42O3Pd2
MW:915.71738
EINECS:610-654-4
Product Categories:chemical reaction,pharm,electronic,materials;organometallic complexes;Catalysis and Inorganic Chemistry;Homogeneous Pd Catalysts;Catalysts-Ligands;Pd;Catalysts for Organic Synthesis;Classes of Metal Compounds;Homogeneous Catalysts;Metal Complexes;Pd (Palladium) Compounds;Synthetic Organic Chemistry;Transition Metal Compounds;Palladium
Mol File:51364-51-3.mol
Tris(dibenzylideneacetone)dipalladium Structure
Tris(dibenzylideneacetone)dipalladium Chemical Properties
Melting point 152-155°C
storage temp. 2-8°C
solubility Soluble in chlorinated solvents, benzene and THF.
form Fine Crystalline Powder
color Purple to black
Water Solubility insoluble
Sensitive Air & Moisture Sensitive
InChIKeyIBXMKLPFLZYRQZ-VCHVFRDLSA-N
CAS DataBase Reference51364-51-3(CAS DataBase Reference)
Safety Information
Hazard Codes Xn
Risk Statements 20/22-36-40
Safety Statements 24/25-36/37
WGK Germany 3
TSCA No
HS Code 28439000
MSDS Information
ProviderLanguage
Tris(dibenzylideneacetone)dipalladium English
Tris(dibenzylideneacetone)dipalladium Usage And Synthesis
DescriptionTris(dibenzylideneacetone) dipalladium (Tris DBA) is used as catalyst for a wide variety of Pd catalyzed reactions including Suzuki coupling, Heck coupling, Negishi coupling, Carroll reaarangement, Trost asymmetric allylic alkylation, Buchwald-Hartwig amination of acryl halides, fluorination of allylic chlorides, arylation of ketones, carbonylation of 1,1-dichloro-1-alkenes, ß-arylation of carboxylic esters, and conversion of aryl and vinyl triflates to aryl and vinyl halides. It is also involved in the synthesis of azepane. Tris DBA is also a novel inhibitor of N-myristoyltransferase-1 with significant antitumor activity.
UsesTris(dibenzylideneacetone)dipalladium is used in the preparation of semiconducting polymers processed from nonchlorinated solvents into high performance thin film transistors. Also used in the synthesis of polymer bulk-heterojunction solar sells as a semiconductor.
Reactions1. Catalyst precursor for conversion of aryl chlorides, triflates, and nonaflates to nitroaromatics.
2. Catalyst for the synthesis of epoxides.
3. Catalytic asymmetric allylic and homoallylic diamination of terminal olefins.
4. Site-selective benzylic sp3 palladium-catalyzed direct arylation.
5. Palladium-catalyzed one-pot synthesis of tricyclic indolines.
6. Active catalyst for the Suzuki-Miyaura coupling of 2-pyridyl nucleophiles.
7. Catalyst in combination with BINAP for the asymmetric Heck Arylation of olefins.
8. Precursor for palladium-catalyzed carbon-nitrigen bond formation.
9. Catalyst for α-arylation of ketones,
10. Cross-coupling of aryl halides with aryl boronic acids.

References
  1. https://en.wikipedia.org/wiki/Tris(dibenzylideneacetone)dipalladium(0)
  2. http://www.sigmaaldrich.com
  3. https://www.alfa.com
  4. https://pubchem.ncbi.nlm.nih.gov
  5. S. S. Bhandarkar, J. Bromberg, C. Carrillo, P. Selvakumar, R. K. Sharma, B. N. Perry, B. Govindarajan, L. Fried, A. Sohn, K. Reddy and J. L. Arbiser, Tris (Dibenzylideneacetone) Dipalladium, a N-Myristoyltransferase-1 Inhibitor, Is Effective against Melanoma Growth In vitro and In vivo, Clinical Cancer Research, 2008, vol. 18, 5743-5748
Chemical Propertiesdark purple solid
Usessuzuki reaction
UsesA cycloaddition catalyst.
Tris(dibenzylideneacetone)dipalladium Preparation Products And Raw materials
Raw materialsSodium acetate-->Benzaldehyde-->Palladium chloride
Preparation Products3-MORPHOLINOPHENYLBORONIC ACID PINACOL ESTER-->4-PYRIDIN-2-YLISOXAZOL-5-AMINE-->3-Morpholinobenzaldehyde
Tag:Tris(dibenzylideneacetone)dipalladium(51364-51-3) Related Product Information
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