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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

Pricing and availability is not currently available.

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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Show Differences

1 of 4

This Item
61300L037561302
form

powder

form

powder

form

powder

form

powder

biological source

bovine milk

biological source

bovine milk

biological source

-

biological source

bovine milk

storage temp.

15-25°C

storage temp.

-

storage temp.

2-8°C

storage temp.

-

solubility

440 g/L

solubility

H2O: 2%, clear to very faintly turbid (light yellow to yellow and light brown-yellow to brown-yellow and light brown to brown)

solubility

-

solubility

H2O: 2%, clear (light yellow to yellow and light brown-yellow to brown-yellow and light brown to brown)

pH

6.5-7.5 (20 °C, 20 g/L in H2O)

pH

6.8±0.5 (25 °C, 2% in H2O)

pH

-

pH

6.8-8.0 (25 °C, 2% in H2O)

Application

Addition of Pd/C to Pd(OH)2/C improves the efficiency of N- or O-debenzylation.[1]
Effectively catalyzes the direct arylation reactions of aryl iodides and bromides in both intra- and intermolecular processes.[2]
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

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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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