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453048

Sigma-Aldrich

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

97%

Sinonimo/i:

PdCl2[P(o-Tol)3]2

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About This Item

Formula condensata:
[(CH3C6H4)3P]2PdCl2
Numero CAS:
40691-33-6
Peso molecolare:
786.06
Numero MDL:
MFCD00274659
Codice UNSPSC:
12161600
ID PubChem:
24868751
NACRES:
NA.22

Livello qualitativo

200

Saggio

97%

Forma fisica

solid

Impiego in reazioni chimiche

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

Punto di fusione

280 °C (dec.) (lit.)

Stringa SMILE

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
OTYPIDNRISCWQY-UHFFFAOYSA-L

Descrizione generale

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

Applicazioni

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.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)

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Certificati d'analisi (COA)

Lot/Batch Number
MKCG1963
MKBS5863V
BCBK3592V
BCBK2761V
MKBJ2560V

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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)
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Articoli

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.

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