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Sigma-Aldrich

Bis(triphenylphosphine)palladium(II) dichloride

98%

Synonym(s):

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

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About This Item

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:
24852524
NACRES:
NA.22

Quality Level

200

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

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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

signalword

Warning

hcodes

H317,H413

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)

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’.

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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)
Synthesizing Highly Fluorinated Oligophenyls via Negishi Coupling of Fluoroarylzinc Pivalates
Engelage E
Synthesis, 54, 711-722 (2021)
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
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