51364-51-3 Usage
Description
Tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3), also known as Tris DBA, is a dark purple solid that serves as a catalyst for a wide variety of Pd-catalyzed reactions. It is a widely used Pd(0) source in Pd-mediated transformations and has been determined through three-dimensional X-ray data to crystallize in a triclinic system.
Uses
1. Used in Semiconductor Applications:
Tris(dibenzylideneacetone)dipalladium is used as a catalyst in the preparation of semiconducting polymers processed from nonchlorinated solvents into high-performance thin film transistors. It is also utilized in the synthesis of polymer bulk-heterojunction solar cells as a semiconductor.
2. Used in Suzuki Reaction:
In the field of organic chemistry, Tris DBA is employed as a catalyst for the Suzuki reaction, a widely used method for the formation of carbon-carbon bonds, particularly in the synthesis of biaryl compounds.
3. Used as a Cycloaddition Catalyst:
Tris(dibenzylideneacetone)dipalladium is utilized as a catalyst in various cycloaddition reactions, which are important for the formation of cyclic compounds in organic synthesis.
4. Used in the Synthesis of Azepane:
Tris DBA is involved in the synthesis of azepane, a seven-membered nitrogen-containing ring, which is a valuable structural motif in pharmaceutical chemistry.
5. Used in Pharmaceutical Applications:
Tris(dibenzylideneacetone)dipalladium is also a novel inhibitor of N-myristoyltransferase-1, which has significant antitumor activity, making it a potential candidate for cancer treatment.
6. Used in Catalyst Research and Development:
Due to its versatility as a catalyst in various Pd-catalyzed reactions, Tris DBA is widely used in research and development for the creation of new catalysts and optimization of existing ones in the fields of chemical synthesis and materials science.
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
https://en.wikipedia.org/wiki/Tris(dibenzylideneacetone)dipalladium(0)
http://www.sigmaaldrich.com
https://www.alfa.com
https://pubchem.ncbi.nlm.nih.gov
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
Check Digit Verification of cas no
The CAS Registry Mumber 51364-51-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,1,3,6 and 4 respectively; the second part has 2 digits, 5 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 51364-51:
(7*5)+(6*1)+(5*3)+(4*6)+(3*4)+(2*5)+(1*1)=103
103 % 10 = 3
So 51364-51-3 is a valid CAS Registry Number.
InChI:InChI=1/3C17H14O.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;;/b13-11+,14-12+;2*13-11-,14-12+;;
51364-51-3Relevant articles and documents
A Simply Synthesized, Tough Polyarylene with Transient Mechanochromic Response
Kempe, Fabian,Brügner, Oliver,Buchheit, Hannah,Momm, Sarah N.,Riehle, Felix,Hameury, Sophie,Walter, Michael,Sommer, Michael
, p. 997 - 1000 (2018)
A simple and high-yielding route to tough polyarylenes of the type poly(meta,meta,para-phenylene) (PmmpP) is developed. PmmpP is tough even in its as-synthesized state which has an intermediate molar mass of Mw≈60 kg mol?1 and exhibits outstanding mechanical properties at further optimized molecular weight of Mw=96 kg mol?1, E=0.9 GPa, ?=300 %. Statistical copolymers with para,para-spiropyran (SP) are mechanochromic, and the toughness allows mechanochromism to be investigated. Strained samples instantaneously lose color upon force release. DFT calculations show this phenomenon to be caused by the PmmpP matrix that allows build-up of sufficiently large forces to be transduced to SP, and the relatively unstable corresponding merocyanine (MC) form arising from the aromatic co-monomer. MC units covalently incorporated into PmmpP show a drastically reduced half life time of 3.1 s compared to 4.5 h obtained for SP derivatives with common 6-nitro substitution.
Enantioselective Synthesis of Homoallylic Azides and Nitriles via Palladium-Catalyzed Decarboxylative Allylation
Vita, Maria Victoria,Caramenti, Paola,Waser, Jerome
supporting information, p. 5832 - 5835 (2015/12/11)
Azides and nitriles are important building blocks for the synthesis of nitrogen-containing bioactive compounds. The first example of enantioselective palladium-catalyzed decarboxylative allylation of α-azido and cyano β-ketoesters is reported. Indanone derivatives were obtained in 50-88% yield/77-97% ee and 46-98% yield/78-93% ee for azide and nitrile substituents, respectively. The required starting materials were synthesized in one step from ketoesters via electrophilic azidation and cyanation using benziodoxole hypervalent iodine reagents. The products could be easily converted into useful nitrogen-containing building blocks, such as triazoles, amides, or α- and β- amino ketones.
