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Sigma-Aldrich

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

97%

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

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

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’.

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Stereoselective total synthesis of (+)-licochalcone E.
Liu Z, et al.
Archives of Pharmacal Research, 34(8), 1269-1276 (2011)
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)
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
Guram, A. S.; Buchwald, S. L
Angewandte Chemie (International Edition in English), 34, 1348-1348 (1995)
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)
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