Tris(dibenzylideneacetone)dipalladium Property

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

Hazard Codes 

Xn

Risk Statements 

20/22-36-40

Safety Statements 

24/25-36/37

WGK Germany 

3

TSCA 

No

HS Code 

28439000

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H317May cause an allergic skin reaction

H411Toxic to aquatic life with long lasting effects

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P272Contaminated work clothing should not be allowed out of the workplace.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P333+P313IF SKIN irritation or rash occurs: Get medical advice/attention.

Tris(dibenzylideneacetone)dipalladium Chemical Properties,Usage,Production

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.

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 Properties

dark purple solid

Uses

suzuki reaction

Uses

A cycloaddition catalyst.

Uses

Tris(dibenzylideneacetone)dipalladium is used in the preparation of semiconducting polymers processed from nonchlorinated solvents into high performance thin film transistors. It is also used as a semiconductor in the synthesis of polymer bulk-heterojunction solar cells.

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) (Pd₂(dba)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.