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Merck

208671

Sigma-Aldrich

Bis(triphenylphosphine)palladium(II) dichloride

98%

Sinónimos:

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

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About This Item

Fórmula lineal:
[(C6H5)3P]2PdCl2
Número de CAS:
Peso molecular:
701.90
Beilstein/REAXYS Number:
4935975
EC Number:
MDL number:
UNSPSC Code:
12161600
PubChem Substance ID:
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

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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

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)

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Referencia del producto
Descripción
Precios

pictograms

Exclamation mark

signalword

Warning

hcodes

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)


Certificados de análisis (COA)

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Visite la Librería de documentos

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)
PdCl2 (PPh3)2-heteropolyacids-catalyzed regioselective hydrocarboxylation of styrene
J. Mol. Catal. A: Chem., 182, 195-207 (2002)
Synthesizing Highly Fluorinated Oligophenyls via Negishi Coupling of Fluoroarylzinc Pivalates
Engelage E
Synthesis, 54, 711-722 (2021)
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
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)

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