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208671

Sigma-Aldrich

Bis(triphenylphosphine)palladium(II) dichloride

98%

Synonyme(s) :

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

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About This Item

Formule linéaire :
[(C6H5)3P]2PdCl2
Numéro CAS:
13965-03-2
Poids moléculaire :
701.90
Numéro Beilstein :
4935975
Numéro CE :
237-744-2
Numéro MDL:
MFCD00009593
Code UNSPSC :
12161600
ID de substance PubChem :
24852524
Nomenclature NACRES :
NA.22

Niveau de qualité

200

Pureté

98%

Forme

solid

Pertinence de la réaction

core: palladium
reagent type: catalyst

Capacité de réaction

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

Chaîne SMILES 

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

Clé InChI

YNHIGQDRGKUECZ-UHFFFAOYSA-L

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Catégories apparentées

Description générale

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)

Produit(s) apparenté(s)

Réf. du produit
Description
Tarif

903124

(Ad−BippyPhos)2PdCl2

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H317,H413

Classification des risques

Aquatic Chronic 4 - Skin Sens. 1A

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

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Certificats d'analyse (COA)

Lot/Batch Number
MKCP3706
MKCP2298
MKCP0832
MKCN9163
MKCN1407

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Consulter la Bibliothèque de documents

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
Nannan Jian et al.
Physical chemistry chemical physics : PCCP, 21(13), 7174-7182 (2019-03-20)
Conjugated fluorophores have been extensively used for fluorescence sensing of various substances in the field of life processes and environmental science, due to their noninvasiveness, sensitivity, simplicity and rapidity. Most existing conjugated fluorophores exhibit excellent light-emitting performance in dilute solutions
Ganesan Bharathiraja et al.
Organic & biomolecular chemistry, 13(9), 2786-2792 (2015-01-22)
Various tetrasubstituted pyrroles/pyrazoles have been prepared from nitro-substituted 1,3-enynes with aromatic amines/hydrazines via a copper-catalyzed cascade aza-Michael addition, cyclization and aromatization at room temperature. This protocol is also effective for the synthesis of tetrasubstituted pyrazoles in high yields.
Hiroaki Imoto et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 21(34), 12105-12111 (2015-07-17)
Aggregation-induced emission (AIE)-active maleimide dyes, namely, 2-p-toluidino-N-p-tolylmaleimide, 3-phenyl-2-toluidino-N-p-tolylmaleimide, 2-p-thiocresyl-3-p-toluidino-N-p-tolylmaleimide, and 2,3-dithiocresyl-N-arylmaleimides, were synthesized by facile synthetic procedures. The dyes show intense emission in the solid state, and emission colors were controlled from green (λmax =527 nm) to orange (λmax =609 nm) by

Articles

Transition-Metal Catalysts

A variety of transition-metal catalysts for the Suzuki coupling reaction are now available in our catalog. The majority of these catalysts are palladium- and nickelbased, typically utilizing phosphine-derived ligands.

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