Dichlorobis(tri-o-tolylphosphine)palladium(II)

Base Information

• Chemical Name: Dichlorobis(tri-o-tolylphosphine)palladium(II)
• CAS No.: 40691-33-6
• Molecular Formula: C₄₂H₄₂Cl₂P₂Pd
• Molecular Weight: 786.069
• Hs Code.: 28439000
• European Community (EC) Number: 664-487-7
• Mol file: 40691-33-6.mol

Synonyms:40691-33-6;Dichlorobis(tri-o-tolylphosphine)palladium(II);TRANS-DICHLOROBIS(TRI-O-TOLYLPHOSPHINE)PALLADIUM(II);MFCD00274659;trans-dichlorobis(tri-o-tolyl-phosphine)palladium(II);PdCl2[P(o-Tol)3]2;Pd((o-tol)3P)2Cl2;Pd(P(o-tolyl)3)2Cl2;Pd[(o-tolyl)3P]2Cl2;SCHEMBL105624;bis(tris(2-methylphenyl)phosphane) palladium dichloride;OTYPIDNRISCWQY-UHFFFAOYSA-L;AMY41916;BCP21896;AKOS024258532;SB40667;SC10409;dichlorobis(tri-o-tolylphosphin)palladium;Dichlorobis(tri-o-tolylphosphine)palladium;PS-15599;SY010266;dichlorobis(tri-o-tolyl-phosphine)palladium;Dichlorobis(tris(o-tolyl)phosphine)palladium;dichloropalladium;bis(tris-o-tolylphosphane);FT-0696077;bis(tri-o-tolylphosphine)palladium(II) chloride;dichlorobis(tri-o-tolyl-phosphine)palladium(II);dichlorobis(tri-o-tolylphosphine)-palladium(II);tris(2-methylphenyl)phosphane;F10008;palladium-bis-(tri-o-tolylphosphine)-dichloride;bis[tri(ortho-tolyl)phosphine] palladium chloride;dichlorobis(tri-o-tolyl phosphine)-palladium(II);dichlorobis(tri-O-tolylphosphine)-palladium (II);bis(tri-o-tolylphosphine)-palladium(II) dichloride;bis-(tri-o-tolylphosphine)palladium(ii) dichloride;bis-(tri-o-tolylphosphine) palladium (II) chloride;bis-(tri-o-tolylphosphine)palladium (II) dichloride;Dichlorobis(tri-o-tolylphosphine)palladium(II), 97%;trans-dichlorobis(tri-o-tolyl phosphine)palladium(ii);Trans-dichlorobis(tri-o-tolylphosphine)palladium (II);DICHLOROBIS(TRI-ORTHO-TOLYLPHOSPHINE)PALLADIUM(II);Dichlorobis(tri-ortho-tolylphosphine)palladium(II), 95%;bis[tris(2-methylphenyl)phosphine] palladium (II) chloride

Chemical Property of Dichlorobis(tri-o-tolylphosphine)palladium(II)

Chemical Property:

• Vapor Pressure: 1.24E-06mmHg at 25°C
• Melting Point: 280 °C (dec.)(lit.)
• Boiling Point: 412.4 °C at 760 mmHg
• Flash Point: 214.6 °C
• PSA: 27.18000
• LogP: 10.11900
• Storage Temp.: Inert atmosphere,Room Temperature
• Sensitive.: Air & Moisture Sensitive
• Solubility.: Soluble in ethanol, benzene, and ethereal solvents.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 6
• Exact Mass: 784.11736
• Heavy Atom Count: 47
• Complexity: 289

Purity/Quality:

95% ^*data from raw suppliers

Dichlorobis[tris(2-methylphenyl)phosphine]palladium ^*data from reagent suppliers

Safty Information:

• Statements: 53
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C.CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C.Cl[Pd]Cl
• General Description: **DICHLOROBIS(TRI-O-TOLYLPHOSPHINE)PALLADIUM(II)** is a palladium(II) complex used as a catalyst in the arylation of organozinc reagents, specifically in coupling reactions between aryl iodides and 2-carboethoxyethylzinc iodide or 3-carboethoxypropylzinc iodide to form β-aryl esters. Its role in these transformations highlights its utility in facilitating carbon-carbon bond formation under mild conditions, contributing to the synthesis of functionalized ester derivatives. **Null** (if no relevant content is found).

Technology Process of Dichlorobis(tri-o-tolylphosphine)palladium(II)

There total 4 articles about Dichlorobis(tri-o-tolylphosphine)palladium(II) which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 66.0%

bis(benzonitrile)palladium(II) dichloride (15617-18-2,39958-10-6,14220-64-5) + tris-(o-tolyl)phosphine (6163-58-2) → trans-dichlorobis(tri-o-tolylphenylphosphane)palladium(II) (40691-33-6,14219-84-2)

Guidance literature:

In toluene; under N2; ligand (2.35 mmol) and Pd-contg. compd. (1.18 mmol) were mixedin toluene; the suspn. was heated at reflux for 21 h; cooling to room t emp.; the solvent was removed and the solid triturated with cold toluene, filtered off, washed with cold toluene and dried in vac.; elem. anal.;

DOI:10.1039/b416525j

Reference yield:

4-(3-(3-[bis[(1,1-dimethylethoxy)carbonyl]amino]-4-methylphenyl)-1,2,4-oxadiazol-5-yl)-1,1,1-trifluoro-2-methylbutan-2-ol (1426671-32-0) + methyl iodide (74-88-4) → dichlorobis(tri-O-tolylphosphine)palladium (40691-33-6,14219-84-2)

Guidance literature:

With sodium hydride; In 1-methyl-pyrrolidin-2-one; mineral oil; at 90 ℃; for 1h;

Reference yield:

tris-(o-tolyl)phosphine (6163-58-2) + palladium dichloride → dichlorobis(tri-O-tolylphosphine)palladium (40691-33-6,14219-84-2)

Guidance literature:

With HCl; In ethanol; water; acetone; PdCl2 in EtOH reacted with HCl soln. and ligand in acetone, refluxed for2 h; washed (EtOH), dried (air), recrystd. (THF);

DOI:10.1016/j.jorganchem.2008.01.005

upstream raw materials:

tris-(o-tolyl)phosphine

4-(3-(3-[bis[(1,1-dimethylethoxy)carbonyl]amino]-4-methylphenyl)-1,2,4-oxadiazol-5-yl)-1,1,1-trifluoro-2-methylbutan-2-ol

methyl iodide

dichloro(1,5-cyclooctadiene)palladium(II)

Downstream raw materials:

chloro-(pyrine-6-thiolato)(tris-o-tolylphosphine)palladium(II)

bis(tri-ortho-tolylphosphine)palladium⁽⁰⁾

chloro-(pyrimidine-2-thiolato)(tris-o-tolylphosphine)palladium(II)

[Pd(1,2,3,4-tetrahydroisoquinolinedithiocarbamate)(tri-o-tolylphosphine)Cl]

Refernces

ARYLATION AND VINYLATION OF 2-CARBOETHOXYETHYLZINC IODIDE AND 3-CARBOETHOXYPROPYLZINC IODIDE CATALYZED BY PALLADIUM

10.1016/S0040-4039(00)84147-7

The research investigates the palladium-catalyzed arylation and vinylation of 2-carboethoxyethylzinc iodide and 3-carboethoxypropylzinc iodide. These organozinc compounds, generated via a Reformatsky type direct metallation of ethyl β-iodopropionate or ethyl γ-iodobutyrate with a zinc-copper couple, serve as key reagents. In the arylation reaction, they couple with aryl iodides in the presence of palladium catalysts such as bis(tri-o-tolylphosphine)palladium(II) chloride to produce 8-aryl and β-aryl esters. For vinylation, they react with vinyl iodides or triflates using tetrakis(triphenylphosphine)palladium(0) as a catalyst to form β,γ-unsaturated esters. The study demonstrates the versatility of these organozinc reagents in synthesizing various ester compounds under palladium catalysis.