Dichlorobis(tri-o-tolylphosphine)palladium(II)

Name: Dichlorobis(tri-<I>o</I>-tolylphosphine)palladium(II)
Brand: ALDRICH
Price: 73.1 USD

97%, solid

Synonym(s):

PdCl₂[P(o-Tol)₃]₂

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About This Item

Linear Formula:

[(CH₃C₆H₄)₃P]₂PdCl₂

CAS Number:

40691-33-6

Molecular Weight:

786.06

MDL number:

MFCD00274659

UNSPSC Code:

12161600

PubChem Substance ID:

24868751

NACRES:

NA.22

Key Documents

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Product Name

Dichlorobis(tri-o-tolylphosphine)palladium(II), 97%

Quality Level

200

assay

97%

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

mp

280 °C (dec.) (lit.)

SMILES string

Cl[Pd]Cl.Cc1ccccc1P(c2ccccc2C)c3ccccc3C.Cc4ccccc4P(c5ccccc5C)c6ccccc6C

InChI

1S/2C21H21P.2ClH.Pd/c2*1-16-10-4-7-13-19(16)22(20-14-8-5-11-17(20)2)21-15-9-6-12-18(21)3;;;/h2*4-15H,1-3H3;2*1H;/q;;;;+2/p-2

InChI key

OTYPIDNRISCWQY-UHFFFAOYSA-L

Related Categories

Catalysts

Cross-Coupling Catalysts

Palladium Catalysts

Transition Metal Catalysts

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This Item	403237	768111	741248
Sigma-Aldrich 453048 Dichlorobis(tri-o-tolylphosphine)palladium(II)	Sigma-Aldrich 403237 Dichlorobis(tricyclohexylphosphine)palladium(II)	Sigma-Aldrich 768111 Dichloro[2,2′-bis(diphenylphosphino)-1,1′-binaphthyl]palladium(II)	Sigma-Aldrich 741248 Bis(triphenylphosphine)palladium(II) dichloride
assay 97%	assay 95%	assay 97%	assay -
reaction suitability reaction type: Buchwald-Hartwig Cross Coupling Reaction, reaction type: Heck Reaction, reaction type: Negishi Coupling, reaction type: Stille Coupling, reagent type: catalyst core: palladium, reaction type: Cross Couplings, reaction type: Sonogashira Coupling, reaction type: Suzuki-Miyaura Coupling, reaction type: Hiyama Coupling	reaction suitability -	reaction suitability -	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
form solid	form solid	form solid	form solid
Quality Level 200	Quality Level 100	Quality Level 100	Quality Level 100
mp 280 °C (dec.) (lit.)	mp 270 °C (dec.) (lit.)	mp 230-300 °C (decomposition)	mp -

General description

Dichlorobis(tri-o-tolylphosphine)palladium(II) is a useful catalyst for C-C and C-N coupling reactions.

Application

Application Guide for Palladium Catalyzed Cross-Coupling Reactions

Catalyst for C-C and C-N coupling reaction.

Dichlorobis(tri-o-tolylphosphine)palladium(II) has been employed as catalyst for the following studies:

Reaction of tributyltin enolates, prepared in situ from tributyltin methoxide and enol acetates, with aryl bromides.[1]
Coupling reaction of aryl bromides with vinylic acetates.[1]
Negishi-Reformatsky coupling reaction of aryl bromides with ethyl 2-(tributylstannyl)acetates.[2]
Synthesis of (E)-methyl 3-(7-indolyl)-2-methacrylate, via Heck reaction.[3]
Synthesis of imidazopyrimidine derivatives.[4]

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)

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Toward the enantioselective total synthesis of lyngbyatoxin A: on the stereocontrolled introduction of the quaternary stereogenic centre.

T?nder JE and Tanner D.

Tetrahedron, 59(35), 6937-6945 (2003)

Guram, A. S.; Buchwald, S. L

Angewandte Chemie (International Edition in English), 34, 1348-1348 (1995)

Design and Synthesis of Imidazopyrimidine Derivatives as Potent iNOS Dimerization Inhibitors.

Guo-Hua Chu et al.

The open medicinal chemistry journal, 3, 8-13 (2009-12-08)

A series of imidazopyrimidine derivatives with the general formula I was synthesized and identified as potent inhibitors of iNOS dimer formation, a prerequisite for proper functioning of the enzyme. Stille and Negishi coupling reactions were used as key steps to

Unexpected Formation of Aryl Ketones by Palladium-Catalyzed Coupling of Aryl Bromides with Vinylic Acetates.

Jean M, et al.

Organic Letters, 9(18), 3623-3625 (2007)

Stereoselective total synthesis of (+)-licochalcone E.

Liu Z, et al.

Archives of Pharmacal Research, 34(8), 1269-1276 (2011)

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Dichlorobis(tri-o-tolylphosphine)palladium(II)