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ChemicalBook--->CAS DataBase List--->51364-51-3

51364-51-3

51364-51-3 Structure

51364-51-3 Structure
IdentificationMore
[Name]

Tris(dibenzylideneacetone)dipalladium
[CAS]

51364-51-3
[Synonyms]

Tris(dibenzylideneacetone)dipalladium
Bis(dibenzylideneacetone)palladium(0)~Pd_2(dba)_3
Tris(dibenzylidenaceTone) dipalladium (O)
TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM,20.3%
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) Can be used to form catalysts in situ by separate addition of ligand dec. 152-155
Tris(dibenzylideneacetone)dipalladium(0), Pd content 22-24%
ChemDose(R), Tris[dibenzylideneacetone]dipalladium(0) impregnated tablets
Tris[dibenzylideneacetone]dipalladium(0), ChemDose(R) tablets
[EINECS(EC#)]

610-654-4
[Molecular Formula]

C51H42O3Pd2
[MDL Number]

MFCD00013310
[Molecular Weight]

915.72
[MOL File]

51364-51-3.mol
Chemical PropertiesBack Directory
[Appearance]

dark purple solid
[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
[InChI]

InChI=1S/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;;/b3*13-11+,14-12+;;
[InChIKey]

IBXMKLPFLZYRQZ-VCHVFRDLSA-N
[CAS DataBase Reference]

51364-51-3(CAS DataBase Reference)
Safety DataBack Directory
[Hazard Codes ]

Xn
[Risk Statements ]

R20/22:Harmful by inhalation and if swallowed .
R36:Irritating to the eyes.
R40:Limited evidence of a carcinogenic effect.
[Safety Statements ]

S24/25:Avoid contact with skin and eyes .
S36/37:Wear suitable protective clothing and gloves .
[WGK Germany ]

3
[TSCA ]

No
[HS Code ]

28439090
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Sodium acetate-->Benzaldehyde-->Palladium chloride
[Preparation Products]

3-MORPHOLINOPHENYLBORONIC ACID PINACOL ESTER-->4-PYRIDIN-2-YLISOXAZOL-5-AMINE-->3-Morpholinobenzaldehyde
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

Tris(dibenzylideneacetone)dipalladium(51364-51-3).msds
Questions And AnswerBack Directory
[Description]

Tris(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, ?-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.
[Uses]

Tris(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.
[Reactions]

1. 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.
Reactions of 51364-51-3_1
Reactions of 51364-51-3_2
[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
Hazard InformationBack Directory
[Chemical Properties]

dark purple solid
[Preparation]

First reported in 1970,Tris(dibenzylideneacetone)dipalladium(0)  is prepared from dibenzylideneacetone and sodium tetrachloropalladate. Because it is commonly recrystallized from chloroform, the complex is often supplied as the adduct [Pd2(dba)3·CHCl3].The purity of samples can be variable.
[General Description]

Tris(dibenzylideneacetone)dipalladium(0) (51364-51-3) participates in the synthesis of azepane. Crystal structure of Pd2(dba)3 has been determined by three-dimensional X-ray data. Crystals of Pd2(dba)3 are reported to crystalize in triclinic system. It is widely used Pd(0) source in Pd-mediated transformations.
[Structure and conformation]

In [Pd2(dba)3], the pair of Pd atoms are separated by 320 pm but are tied together by dba units.The Pd(0) centres are bound to the alkene parts of the dba ligands. 
Spectrum DetailBack Directory
[Spectrum Detail]

Tris(dibenzylideneacetone)dipalladium(51364-51-3)FT-IR
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

Tris(dibenzylideneacetone)dipalladium(0), 97%(51364-51-3)
[Alfa Aesar]

Tris(dibenzylideneacetone)dipalladium(0), Pd 21.5% min(51364-51-3)
[Sigma Aldrich]

51364-51-3(sigmaaldrich)
[TCI AMERICA]

Tris(dibenzylideneacetone)dipalladium(0),>75.0%(T)(51364-51-3)
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