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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

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About This Item

Linear Formula:
Pd
MDL number:
MFCD03427452
UNSPSC Code:
12141733
eCl@ss:
38191001
PubChem Substance ID:
24852343
NACRES:
NA.22

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.

sustainability

Greener Alternative Product

extent of labeling

5 wt. % loading

greener alternative category

Enabling,

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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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

pictograms

Health hazardEnvironment
GHS08,GHS09

signalword

Danger

Hazard Classifications

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

target_organs

Central nervous system,Blood,Immune system,Kidney

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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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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 & 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 and 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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