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205737

Sigma-Aldrich

Palladium on calcium carbonate

greener alternative

extent of labeling: 5 wt. % loading, poisoned with lead

Synonym(s):
Pd
Linear Formula:
Pd
MDL number:
eCl@ss:
38191001
PubChem Substance ID:
NACRES:
NA.22

Quality Level

form

powder

autoignition temp.

>1120 °F

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

greener alternative product characteristics

Design for Energy Efficiency
Learn more about the Principles of Green Chemistry.

extent of labeling

5 wt. % loading

greener alternative category

SMILES string

[Ca++].[Pd++].[O-]C([O-])=O.[O-]C([O-])=O

InChI

1S/2CH2O3.Ca.Pd/c2*2-1(3)4;;/h2*(H2,2,3,4);;/q;;2*+2/p-4

InChI key

XGLHAVVVUOEGIO-UHFFFAOYSA-J

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This Item
205680205672407305
Palladium on carbon extent of labeling: 5 wt. % loading (dry basis), matrix activated carbon support

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Palladium on carbon extent of labeling: 30 wt. % loading, matrix activated carbon support

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Palladium on carbon

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

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

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

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

autoignition temp.

>1120 °F

autoignition temp.

-

autoignition temp.

-

autoignition temp.

-

greener alternative product characteristics

Design for Energy Efficiency
Learn more about the Principles of Green Chemistry.

greener alternative product characteristics

Design for Energy Efficiency
Learn more about the Principles of Green Chemistry.

greener alternative product characteristics

Design for Energy Efficiency
Learn more about the Principles of Green Chemistry.

greener alternative product characteristics

Design for Energy Efficiency
Learn more about the Principles of Green Chemistry.

extent of labeling

5 wt. % loading

extent of labeling

5 wt. % loading (dry basis)

extent of labeling

1 wt. % loading

extent of labeling

30 wt. % loading

greener alternative category

Enabling

greener alternative category

Enabling

greener alternative category

Enabling

greener alternative category

Enabling

General description

We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for energy efficiency. Find details here.

Application

Catalyst for:
  • Aqueous Heck coupling and hydroarylation
  • Reduction reactions
  • Hydrogenation reactions
Palladium on calcium carbonate (Pd/CaCO3) can be used as a green catalyst for a variety of applications such as:
  • formation of an efficient catalytic system for Heck coupling reaction and hydroarylation reaction
  • synthesis of Lindlar catalyst for selective hydrogenation of alkynes
  • a catalytic reservoir in Miyaura-Suzuki cross-coupling reactions
  • Stille cross-coupling reactions

Signal Word

Danger

Hazard Classifications

Aquatic Chronic 1 - Flam. Sol. 1 - Lact. - Repr. 1A - STOT RE 2

Storage Class Code

4.1B - Flammable solid hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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Ligand-free Stille cross-coupling reaction using Pd/CaCO3 as catalyst reservoir
Coelho AV, et al.
Tetrahedron Letters, 48(43), 7671-7674 (2007)
Miyaura-Suzuki cross-coupling reactions: the role of Pd/CaCO3 as catalyst reservoir
Oliveira BL and Antunes OAC
Letters in Organic Chemistry, 4(1), 13-15 (2007)
Palladium on Calcium Carbonate Combined to 2-Hydroxypropyl-alpha/beta-cyclodextrins: A Selective Catalytic System for Aqueous Heck Coupling and Hydroarylation
Senra JD, et al.
advanced synthesis and catalysis, 350(16), 2551-2558 (2008)
Palladium on Calcium Carbonate Combined to 2-Hydroxypropyl-alpha/beta-cyclodextrins: A Selective Catalytic System for Aqueous Heck Coupling and Hydroarylation
Senra JD, et al.
Advanced Synthesis & Catalysis, 350(16), 2551-2558 (2008)
Chun Wong Aaron Chan et al.
Nature communications, 5, 5787-5787 (2014-12-20)
Lindlar catalysts comprising of palladium/calcium carbonate modified with lead acetate and quinoline are widely employed industrially for the partial hydrogenation of alkynes. However, their use is restricted, particularly for food, cosmetic and drug manufacture, due to the extremely toxic nature

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