69861-71-8

Basic information

• Product Name: Bis[Tris(2-methylphenyl)phosphine]palladium
• Synonyms: Bis[Tris(2-methylphenyl)phosphine]palladium;Bis[tris(2-methylphenyl)phosphine]palladium 97%;Bis(tri-o-tolylphosphine)palladium(0), min. 98%;Bis(tri-o-tolylphosphine)palladiuM(0), Pd 14.9%;Bis(tri-o-tolylphosphine)palladiuM(0),98%;Palladium bis(tri-o-tolylphosphine);Bis(tris(2-tolyl)phosphine)palladium;Pd[(o-tol)3P]2
• CAS NO: 69861-71-8
• Molecular Formula: C₄₂H₄₂P₂Pd
• Molecular Weight: 715.162
• Product Categories: organometallic complex;Pd
• Mol File: 69861-71-8.mol
• Article Data: 9

Chemical Properties

• Melting Point: 220-225℃
• Appearance: yellow/crystal
• Storage Temp.: ?20°C
• Water Solubility: Insoluble in water.
• Sensitive: Air Sensitive
• CAS DataBase Reference: Bis[Tris(2-methylphenyl)phosphine]palladium(CAS DataBase Reference)
• NIST Chemistry Reference: Bis[Tris(2-methylphenyl)phosphine]palladium(69861-71-8)
• EPA Substance Registry System: Bis[Tris(2-methylphenyl)phosphine]palladium(69861-71-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 69861-71-8(Hazardous Substances Data)

Usage

Description

Bis[Tris(2-methylphenyl)phosphine]palladium, also known as Bis(tri-o-tolylphosphine)palladium(0), is a palladium-based organophosphine compound that serves as a versatile and efficient catalyst in various chemical reactions. It is characterized by its ability to facilitate the formation of carbon-carbon and carbon-heteroatom bonds, making it a valuable asset in the field of organic synthesis.

Uses

Used in Chemical Synthesis:
Bis[Tris(2-methylphenyl)phosphine]palladium is used as a catalyst for palladium-catalyzed cross-coupling reactions, which are essential in the formation of carbon-carbon bonds. These reactions are widely employed in the synthesis of complex organic molecules, including pharmaceuticals, agrochemicals, and advanced materials.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Bis[Tris(2-methylphenyl)phosphine]palladium is used as a catalyst for the amination and arylation reactions, which are crucial for the synthesis of various drug molecules. These reactions allow for the introduction of nitrogen-containing functional groups and aromatic rings, respectively, into the molecular structure, enhancing the biological activity and pharmacological properties of the resulting compounds.
Used in Material Science:
In the field of material science, Bis[Tris(2-methylphenyl)phosphine]palladium is utilized as a catalyst for Kumada coupling and Heck coupling reactions. These processes are vital in the synthesis of conjugated polymers and other advanced materials with unique electronic, optical, and mechanical properties. The catalyst plays a significant role in enabling the formation of these materials with high efficiency and selectivity.
Used in Research and Development:
Bis[Tris(2-methylphenyl)phosphine]palladium is also employed in research and development laboratories, where it is used to explore new reaction pathways and develop innovative synthetic methods. Its versatility and efficiency make it an indispensable tool for chemists working on the design and synthesis of novel organic compounds and materials.

Reactions

Catalyst used in the palladium-catalyzed amination of aryl and heteroaryl tosylates at room temperature.

Upstream product

• 6163-58-2 tris-(o-tolyl)phosphine 
• 32005-36-0 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 
• 183862-94-4 [Pd(OCOCH₃)(HN(C₂H₅)2)(C₂₁H₂₀P)] 
• 40691-33-6 dichlorobis(tri-O-tolylphosphine)palladium 
• 172418-32-5 trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II) 
• 52409-22-0 tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ 
• 210691-06-8 (μ-η(2),η(2)-C7H12)[Pd(η(2),η(2)-C7H12)]2 

Downstream Products

• 727722-34-1 bromo(4-chlorophenyl)(1,2-bis(diphenylphosphino)benzene)palladium 
• 727722-37-4 bromo(4-(trifluoromethyl)phenyl)(1,2-bis(diphenylphosphino)benzene)palladium 
• 330783-82-9 [Pd(P(o-tolyl)3)(2-Me-5-t-Bu-C6H3)(μ-Br)]2 
• 330980-08-0 [Pd(P(o-tolyl)3)(2-Me-5-t-Bu-C6H3)(μ-I)]2 
• 727722-32-9 bromo(phenyl)(1,2-bis(diphenylphosphino)benzene)palladium 
• 727722-36-3 bromo(4-methoxyphenyl)(1,2-bis(diphenylphosphino)benzene)palladium 
• 727722-33-0 bromo(4-cyanophenyl)(1,2-bis(diphenylphosphino)benzene)palladium 
• 727722-35-2 bromo(3-chlorophenyl)(1,2-bis(diphenylphosphino)benzene)palladium 

Relevant articles and documents

Capturing a ghost. synthesis and structural characterization of Pd(dba)[P(o -Tol)3]2

In an effort to improve upon a literature synthesis of bis[tris(o-tolyl) phosphine]palladium(0) (1) from tris(o-tolyl)phosphine and Pd 2(dba)3, we instead isolated a new compound which proved to have the composition Pd(dba)[P(o-Tol)3]2 (2), upon analysis by X-ray crystallography. While this is not the first known palladium compound containing both dba and phosphine ligands, it is, to our knowledge, the first containing dba and tris(o-tolyl)phosphine. This is significant, because mixtures of Pd2(dba)3 and tris(o-tolyl)phosphine are routinely used in cross-coupling protocols, and palladium complexes containing dba and tris(o-tolyl)phosphine have been cited as intermediates in organometallic and polymerization reactions. The most interesting crystallographic parameter for 2 is an abnormally long Pd-P bond length of 2.388(1) A, which we believe is the cause of this complex's metastability. We also present an alternative synthesis of 1 that does not require a large excess of phosphine.

Stoichiometric and Catalytic Aryl-Perfluoroalkyl Coupling at Tri-tert-butylphosphine Palladium(II) Complexes

This Communication describes studies of Ph-RF (RF = CF3 or CF2CF3) coupling at Pd complexes of general structure (PtBu3)PdII(Ph)(RF). The CF3 analogue participates in fast Ph-CF3 coupling (II complex. Furthermore, they show that this undesired pathway can be circumvented by changing from a CF3 to a CF2CF3 ligand. Ultimately, the insights gained from stoichiometric studies enabled the identification of Pd(PtBu3)2 as a catalyst for the Pd-catalyzed cross-coupling of aryl bromides with TMSCF2CF3 to afford pentafluoroethylated arenes.

1,6-Diene complexes of palladium(0) and platinum(0): Highly reactive sources for the naked metals and [L-M0] fragments

The complexes (cod)MCl2 (M = Pd, Pt; cod = cis,cis-1,5-cyclooctadiene) react with Li2(cot) (cot = cyclooctatetraene) in a 1,6-diene/diethyl ether mixture (1,6-diene = hepta-1,6-diene, diallyl ether, dvds (1,3-divinyl- 1,1,3,3-tetramethyldisiloxane)) to afford the isolated homoleptic dinuclear Pd0 and Pt0 compounds Pd2(C7H12)3 (1), Pd2(C6H10O)3·C6H10O (2'; 2: Pd2(C6H10O)3), Pd2(dvds)3 (3), and Pt2(C7H12)3 (4). When 1-4 are treated with additional 1,6-diene the equally homoleptic but mononuclear derivatives of type M(1,6-diene)2 (5-8) and with ethene the mixed alkene complexes (C2H4)M(1,6-diene) (9-12) are obtained in solution. Complexes 1-12 react with donor ligands such as phosphanes, phosphites, or (t)BuNC to give isolated complexes of types L-M(1,6-diene) (13-41), which have also been prepared by other routes. In all complexes the metal centers are TP-3 coordinated: complexes 1-4 contain chelating and bridging 1,6-diene ligands, whereas the other complexes contain a chelating 1,6-diene ligand and an η2-alkene (5-12) or η1-donor ligand (13-41). Of the studied 1,6-diene complexes the hepta-1,6-diene derivatives are most reactive, while the diallyl ether complexes are often more convenient to handle. The readily isolable dinuclear hepta-1,6-diene and diallyl ether complexes 1, 2', and 4, and their mononuclear pure olefin derivatives are among the most reactive sources for naked Pd0 and Pt0. The corresponding L-M(1,6-diene) complexes are equally reactive precursor compounds for the generation of [L-M0] fragments in solution, which for M =Pd are available otherwise only with difficulty. The results are significant for the operation of naked Pd0 and L-Pd0 catalysts in homogeneous catalysis.