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741248

Sigma-Aldrich

Bis(triphenylphosphine)palladium(II) dichloride

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:
4935975
EC Number:
237-744-2
MDL number:
MFCD00009593
UNSPSC Code:
12161600
PubChem Substance ID:
329765477
NACRES:
NA.22

form

solid

reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Cross Couplings
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
core: palladium
reagent type: ligand

functional group

phosphine

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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Application

Application Guide for Palladium Catalyzed Cross-Coupling Reactions
Bis(triphenylphosphine)palladium(II) dichloride is generally used as a catalyst for the synthesis of conjugated polymers via Stille coupling. It is also applicable to other coupling reactions such as Suzuki- and Sonogashira-coupling reactions

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Description
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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

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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New oligomeric poly (ether-imide) s containing diphenylsilane and dibenzofuran moieties. Synthesis and characterization.
Tundidor-Camba A, et al.
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Alishah MM, et al.
Turkish Journal of Chemistry, 42(2), 572-585 (2018)
Influence of catalytic systems in Stille polymerization on the electrochromic performance of diketopyrrolopyrrole-based conjugated polymers.
Neo WT, et al.
Materials Chemistry Frontiers. (2018)
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

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