Skip to Content
Merck
All Photos(2)

Key Documents

More Documents

453048

Sigma-Aldrich

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

97%

Synonym(s):

PdCl2[P(o-Tol)3]2

Sign Into View Organizational & Contract Pricing
All Photos(2)

About This Item

Linear Formula:
[(CH3C6H4)3P]2PdCl2
CAS Number:
40691-33-6
Molecular Weight:
786.06
MDL number:
MFCD00274659
UNSPSC Code:
12352300
PubChem Substance ID:
24868751
NACRES:
NA.22

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

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.
  • Coupling reaction of aryl bromides with vinylic acetates.
  • Negishi-Reformatsky coupling reaction of aryl bromides with ethyl 2-(tributylstannyl)acetates.
  • Synthesis of (E)-methyl 3-(7-indolyl)-2-methacrylate, via Heck reaction.
  • Synthesis of imidazopyrimidine derivatives.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
Guram, A. S.; Buchwald, S. L.
Journal of the American Chemical Society, 116, 7901-7901 (1994)
Guram, A. S.; Buchwald, S. L
Angewandte Chemie (International Edition in English), 34, 1348-1348 (1995)
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
Stereoselective total synthesis of (+)-licochalcone E.
Liu Z, et al.
Archives of Pharmacal Research, 34(8), 1269-1276 (2011)
View All Related Papers

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.

Heck Reaction

The Heck reaction is the palladium catalyzed cross-coupling reaction between alkenes and aryl or vinyl halides (or triflates) to afford substituted alkenes.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service