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727733

Sigma-Aldrich

[2,6-Bis[(di-1-piperidinylphosphino)amino]phenyl]palladium(II) chloride

≥98.0% (AT)

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About This Item

Empirical Formula (Hill Notation):
C26H45ClN6P2Pd
CAS Number:
955035-37-7
Molecular Weight:
645.50
MDL number:
MFCD17019351
UNSPSC Code:
12352300
PubChem Substance ID:
329764343

Assay

≥98.0% (AT)

form

lumps

reaction suitability

core: palladium
reaction type: Buchwald-Hartwig Cross Coupling Reaction
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

SMILES string

Cl[Pd]c1c(NP(N2CCCCC2)N3CCCCC3)cccc1NP(N4CCCCC4)N5CCCCC5

InChI

1S/C26H45N6P2.ClH.Pd/c1-5-16-29(17-6-1)33(30-18-7-2-8-19-30)27-25-14-13-15-26(24-25)28-34(31-20-9-3-10-21-31)32-22-11-4-12-23-32;;/h13-15,27-28H,1-12,16-23H2;1H;/q;;+1/p-1

InChI key

CSXBAGCRLXPPDX-UHFFFAOYSA-M

Application

Palladium catalyst for CC coupling reactions
  • Performs Suzuki reactions at low loadings
  • High activity at ppm levels for Heck reactions and Sonogashira couplings

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315

Hazard Classifications

Skin Irrit. 2

Storage Class Code

13 - Non 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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Bolliger, J. L. and Frech,C. M.,
Advanced Synthesis & Catalysis, 352, 1075-1080 (2010)
Short, facile, and high-yielding synthesis of extremely efficient pincer-type suzuki catalysts bearing aminophosphine substituents.
Jeanne L Bolliger et al.
Angewandte Chemie (International ed. in English), 46(34), 6514-6517 (2007-07-27)
Bolliger, J. L. and Frech,C. M.
Advanced Synthesis & Catalysis, 351, 891-902 (2009)
Jeanne L Bolliger et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 14(26), 7969-7977 (2008-07-12)
The aminophosphine-based pincer complexes [C6H3-2,6-(XP(piperidinyl)2)2Pd(Cl)] (X=NH 1; X=O 2) are readily prepared from cheap starting materials by sequential addition of 1,1',1''-phosphinetriyltripiperidine and 1,3-diaminobenzene or resorcinol to solutions of [Pd(cod)(Cl)2] (cod=cyclooctadiene) in toluene under N2 in "one pot". Compounds 1 and
Comparative Study of the Frech Catalyst with Two Conventional Catalysts in the Heck Synthesis of 2,4-Diaminopyrimidine-based Antibiotics.
Baskar Nammalwar et al.
Organic preparations and procedures international, 45(1), 66-71 (2013-06-22)
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