212911

Sigma-Aldrich

Palladium hydroxide on carbon

extent of labeling: 20 wt. % loading (dry basis), matrix carbon, wet support

Synonym(s):
Pd(OH)2/C, Pearlman’s catalyst
Empirical Formula (Hill Notation):
H2O2Pd
CAS Number:
Molecular Weight:
140.43
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

contains

≤50% water

Quality Level

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

extent of labeling

20 wt. % loading (dry basis)

matrix

carbon, wet support

SMILES string

O[Pd]O

InChI

1S/2H2O.Pd/h2*1H2;/q;;+2/p-2

InChI key

NXJCBFBQEVOTOW-UHFFFAOYSA-L

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Packaging

1, 10, 50, 500 g in glass bottle

Application

Addition of Pd/C to Pd(OH)2/C improves the efficiency of N- or O-debenzylation.
Effectively catalyzes the direct arylation reactions of aryl iodides and bromides in both intra- and intermolecular processes.
Particularly active for hydrogenolysis of benzyl-nitrogen bonds, and has proven successful even where other palladium-on-carbon catalysts have failed.

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

Synthetic Communications, 36, 925-925 (2006)
Mathieu Parisien et al.
The Journal of organic chemistry, 70(19), 7578-7584 (2005-09-10)
[reactions: see text] Palladium hydroxide on carbon (Pearlman's catalyst) effectively catalyzes direct arylation reactions of aryl iodides and bromides, providing excellent arylation-to-hydrodehalogenation ratios (>30:1) with broad scope for both intra- and intermolecular arylation processes. Studies aimed at determining the nature...
Hosmane, R. S.; Bhadti, V. S.; Lim, B. B.
Synthesis, 1095-1095 (1990)
Zhao, S.; Freeman, J. P.; Szmuszkovicz, J.
The Journal of Organic Chemistry, 57, 4051-4051 (1992)
Prugh, J. D.; Rooney, C. S. et al.
Tetrahedron Letters, 26, 2947-2947 (1985)

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