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744220

Sigma-Aldrich

Dichlorobis(dicyclohexyl-1-piperidinylphosphine)palladium(II)

≥97.0% (CHN)

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About This Item

Empirical Formula (Hill Notation):
C34H64Cl2N2P2Pd
CAS Number:
1227935-55-8
Molecular Weight:
740.16
MDL number:
MFCD22417201
UNSPSC Code:
12352300
PubChem Substance ID:
329765681

Assay

≥97.0% (CHN)

form

powder

composition

carbon, 53.5-56.8%

reaction suitability

core: palladium
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

suitability

conforms to structure for Infrared spectrum

SMILES string

Cl[Pd]Cl.C1CCC(CC1)P(C2CCCCC2)N3CCCCC3.C4CCC(CC4)P(C5CCCCC5)N6CCCCC6

InChI

1S/2C17H32NP.2ClH.Pd/c2*1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;;;/h2*16-17H,1-15H2;2*1H;/q;;;;+2/p-2

InChI key

DGAATSPGVXMFKV-UHFFFAOYSA-L

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
BCBH4023V
BCBH4023

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Roman Gerber et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 18(29), 8901-8905 (2012-06-16)
Cis all round: Dichlorobis[1-(dicyclohexylphosphanyl)piperidine]palladium, [(P{(NC(5)H(10))(C(6)H(11))(2)})(2)Pd(Cl)(2)], is a highly efficient alkyne hydrothiolation catalyst and the first generally applicable system that selectively generates cis-configured anti-Markovnikov adducts in excellent yields within only a few minutes at 120 °C in the presence of only 0.05 mol %
Access to 2-Aminopyridines - Compounds of Great Biological and Chemical Significance
Bolliger, J. L.; et al.
Advanced Synthesis & Catalysis, 353, 945-945 (2011)
Mizoroki-Heck reactions catalyzed by dichloro{bis[1-(dicyclohexylphosphanyl)piperidine]}palladium. Palladium nanoparticle formation promoted by (water induced) ligand degradation.
Oberholzer, M., et al.
Advanced Synthesis & Catalysis, 354, 627-627 (2012)
Jeanne L Bolliger et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 16(36), 11072-11081 (2010-08-18)
[Pd(Cl)(2){P(NC(5)H(10))(C(6)H(11))(2)}(2)] (1) has been prepared in quantitative yield by reacting commercially available [Pd(cod)(Cl)(2)] (cod=cyclooctadiene) with readily prepared 1-(dicyclohexylphosphanyl)piperidine in toluene under N(2) within a few minutes at room temperature. Complex 1 has proved to be an excellent Negishi catalyst, capable
Roman Gerber et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 18(10), 2978-2986 (2012-02-03)
Dichloro[bis{1-(dicyclohexylphosphanyl)piperidine}]palladium [(P{(NC(5)H(10))(C(6)H(11))(2)})(2)PdCl(2)] (1) is a highly active and generally applicable C-C cross-coupling catalyst. Apart from its high catalytic activity in Suzuki, Heck, and Negishi reactions, compound 1 also efficiently converted various electronically activated, nonactivated, and deactivated aryl bromides, which may
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