Skip to Content
Merck
All Photos(5)

Documents

208671

Sigma-Aldrich

Bis(triphenylphosphine)palladium(II) dichloride

98%

Synonym(s):

Dichlorobis(triphenylphosphine)palladium(II), Palladium(II)bis(triphenylphosphine) dichloride, PdCl2(PPh3)2

Sign Into View Organizational & Contract Pricing
All Photos(5)

About This Item

Linear Formula:
[(C6H5)3P]2PdCl2
CAS Number:
13965-03-2
Molecular Weight:
701.90
Beilstein:
4935975
EC Number:
237-744-2
MDL number:
MFCD00009593
UNSPSC Code:
12161600
PubChem Substance ID:
24852524
NACRES:
NA.22

Assay

98%

form

solid

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

Looking for similar products? Visit Product Comparison Guide

General description

Bis(triphenylphosphine)palladium(II) dichloride ((PdCl2(PPh3)2) is an organopalladium complex containing tertiary phosphine ligands that is commonly used in C-C bond forming reactions such as Heck arylation, Suzuki coupling, Stille coupling, and Sonogashira coupling.

Application

Application Guide for Palladium Catalyzed Cross-Coupling Reactions
Bis(triphenylphosphine)palladium(II) dichloride can be used as a catalyst in the:
  • Coupling of 2-iodoanisole and terminal alkynes to synthesize 2,3-disubstituted benzofurans.
  • Copper-free Sonogashira cross-coupling reaction to synthesize diphenylacetylene.
  • Regioselective hydrocarboxylation of styrene.
  • Negishi coupling of fluoroarylzinc pivalates to prepare fluorinated oligophenyls.
  • Coupling of iodo-α-β-unsaturated esters to afford tetrasubstituted olefins.
For small scale and high throughput uses, product is also available as ChemBeads (927759)

related product

Product No.
Description
Pricing

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H317,H413

Hazard Classifications

Aquatic Chronic 4 - Skin Sens. 1A

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Phenoxide-assisted P-C bond cleavage in PdCl2 (PPh3) 2 under very mild conditions
Yasuda H, et al.
Journal of Organometallic Chemistry, 691, 1307-1310 (2006)
Modular Synthesis of Phosphino Hydrazones and Their Use as Ligands in a Palladium-Catalysed Cu-Free Sonogashira Cross-Coupling Reaction
Baweja S, et al.
ChemPlusChem, e202300163-e202300163 (2023)
Synthesis of 2, 3-Disubstituted Benzofurans by the Palladium-Catalyzed Coupling of 2-Iodoanisoles and Terminal Alkynes, Followed by Electrophilic Cyclization: 3-Iodo-2-phenylbenzofuran
Yao T, et al.
J. Org. Synth., 91, 283-292 (2014)
Alison B Lemay et al.
The Journal of organic chemistry, 71(9), 3615-3618 (2006-04-22)
The efficient regioselective and stereospecific synthesis of tetrasubstituted olefins using a mild and convenient method is disclosed. 2-Alkynyl esters are selectively converted to E-beta-chloro-alpha-iodo-alpha,beta-unsaturated esters by exposure to Bu4NI in refluxing dichloroethane. These products are produced cleanly, regio- and stereoselectively
PdCl2 (PPh3)2-heteropolyacids-catalyzed regioselective hydrocarboxylation of styrene
J. Mol. Catal. A: Chem., 182, 195-207 (2002)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service