412740

Bis(triphenylphosphine)palladium(II) dichloride

• Synonym(s): Dichlorobis(triphenylphosphine)palladium(II), Palladium(II)bis(triphenylphosphine) dichloride, PdCl₂(PPh₃)₂
• Linear Formula: [(C₆H₅)₃P]₂PdCl₂
• CAS Number: 13965-03-2
• Molecular Weight: 701.90
• Beilstein/REAXYS Number: 4935975
• EC Number: 237-744-2
• MDL number: MFCD00009593
• UNSPSC Code: 12161600
• PubChem Substance ID: 24865821
• NACRES: NA.22

Properties

• form: solid
• Quality Level: 200
• reaction suitability: core: palladium; reaction type: Buchwald-Hartwig Cross Coupling Reaction; reaction type: Heck Reaction; reaction type: Hiyama Coupling; reaction type: Negishi Coupling; reaction type: Sonogashira Coupling; reaction type: Stille Coupling; reaction type: Suzuki-Miyaura Coupling; reagent type: catalyst
• SMILES string: Cl[Pd]Cl.c1(P(c2ccccc2)c3ccccc3)ccccc1.c4(P(c5ccccc5)c6ccccc6)ccccc4
• 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

Description

General description

Bis(triphenylphosphine)palladium(II) dichloride is an organometallic complex. It is an efficient cross-coupling catalyst for C-C coupling reaction, such as Negishi coupling, Suzuki coupling, Sonogashira coupling and Heck coupling reaction. Detection of bis(triphenylphosphine)palladium(II) dichloride by electrospray ionization quadrupole ion trap mass spectrometry using different imidazolium salts as the charge carrier has been reported. It is employed as catalyst for the Heck reaction medium.

Application

Application Guide for Palladium Catalyzed Cross-Coupling Reactions

Bis(triphenylphosphine)palladium(II) dichloride was employed in the following studies:

• As model catalyst for the evaluation of functionalized silica′s for the adsorptive recovery of homogeneous catalysts, via its interaction with metal centre.
• As catalyst in the synthesis of diphenylacetylene.
• One-pot synthesis of furoquinolines, via Pd-catalyzed Sonogashira coupling followed by Cu(I) catalyzed ring closure.
• Catalyst for Sonogashira coupling of aryl alkynes to 2-bromothiazole and 2-bromothiophene.

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H317,H413
• pcodes: P261 - P272 - P273 - P280 - P302 + P352 - P333 + P313
• Hazard Classifications: Aquatic Chronic 4 - Skin Sens. 1A
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)