CAS 13965-03-2 Bis(triphenylphosphine)palladium(II) Dichloride

Synonyms

TRANS-BIS-(TRIPHENYLPHOSPHINE)PALLADIUM DICHLORIDE; 13965-03-2; 28966-81-6; AC1L36TY; SC-01002; LS-192238; bis(triphenylphosphine) palladiuml(ii) dichloride; bis(triphenylphosphine) palladium (ii) chloride; FC0823; EINECS 237-744-2;

IUPAC Name

palladium(2+);triphenylphosphane;dichloride;

Molecular Weight

701.904g/mol

Molecular Formula

C36H30Cl2P2Pd;

Canonical SMILES

C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Cl-].[Cl-].[Pd+2];

InChI

InChI=1S/2C18H15P.2ClH.Pd/c2*1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;;;/h2*1-15H;2*1H;/q;;;;+2/p-2;

InChI Key

YNHIGQDRGKUECZ-UHFFFAOYSA-L;

Storage

Store below +30°C.

Complexity

202

Covalently-Bonded Unit Count

EC Number

237-744-2

Exact Mass

700.023g/mol

H-Bond Acceptor

Heavy Atom Count

Monoisotopic Mass

700.023g/mol

Rotatable Bond Count

Topological Polar Surface Area

0A^2

Application

Bis(triphenylphosphine)palladium(II) dichloride serves a crucial role as an organometallic complex prominently used in catalyzing a variety of carbon-carbon coupling reactions critical to organic synthesis. This compound is particularly effective in facilitating processes like Negishi, Suzuki, Sonogashira, and Heck coupling reactions. Beyond its application in these reactions, it acts as a precatalyst in several specialty transformations such as the carbonylative cyclization of malonate derivatives, double allylation of activated olefins, the three-component preparation of tetrahydrofurans, and the homocoupling of terminal alkynes. Furthermore, it has significant applications in the direct palladium-catalyzed alkynylation of N-fused heterocycles, tandem Heck reactions combined with C-H functionalization, and the direct arylation of tautomerizable heterocycles. This yellow solid, insoluble in water yet soluble in certain organic solvents like toluene and benzene, also contributes to the formation of crystallized metallacyclic complexes with potential anti-inflammatory and antifungal properties, demonstrating its versatility and importance in the field of organometallic catalysis.

January 16, 2025

Efficient Catalyst for Complex Reactions

Bis(triphenylphosphine)palladium(II) dichloride facilitated smooth Negishi and Heck couplings in our lab. Its solubility in toluene and benzene enhanced reaction conditions, proving invaluable for synthesizing complex organic molecules. Highly recommend for organometallic research.