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Key Documents

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

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About This Item

Empirical Formula (Hill Notation):
H2O2Pd
CAS Number:
Molecular Weight:
140.43
EC Number:
MDL number:
UNSPSC Code:
12161600
PubChem Substance ID:
NACRES:
NA.22

form

powder

Quality Level

contains

≤50% water

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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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.

Product can be used with our benchtop hydrogen generator, H-Genie Lite (Z744083)

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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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
Synthetic Communications, 36, 925-925 (2006)
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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