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441902 Sigma-Aldrich

Cesium carbonate

ReagentPlus®, 99%

Synonym: Carbonic acid dicesium

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Properties

Related Categories Acids & Bases, Bases, Cesium Salts, Chemical Synthesis, Essential Chemicals,
grade   ReagentPlus®
InChI Key   FJDQFPXHSGXQBY-UHFFFAOYSA-L
assay   99%
form   powder and chunks
mp   610 °C (dec.) (lit.)

Description

General description

Cesium carbonate is a powerful inorganic base widely used in organic synthesis. It is a potential chemoselective catalyst for the reduction of aldehydes and ketones to alcohols. It is employed as base for the Heck coupling reaction of 4-trifluoromethyl-1-chlorobenzene and aryl chlorides.

Application

Cesium carbonate is an attractive base that finds more and more applications in coupling chemistry.

Cesium carbonate has been employed as catalyst for:
• Aerobic oxidation of primary alcohols.
• 1,4-addition.

Cesium carbonate has been used as reagent for the following studies:
• Synthesis of phosphazene derivatives.
• Constrictive binding interactions.
• Intramolecular C-N cross coupling reactions.
• Dehydohalogenative polycondensation.

Promotes the efficient O-alkylation of alcohols to form mixed alkyl carbonates.

Packaging

5, 50, 100, 250, 500 g in poly bottle

Legal Information

ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
2
RTECS 
FK9400000

Documents

Certificate of Analysis

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Certificate of Origin

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Frequently Asked Questions

Which document(s) contains shelf-life or expiration date information for a given product?
If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.
How do I get lot-specific information or a Certificate of Analysis?
The lot specific COA document can be found by entering the lot number above under the "Documents" section.
What is Product 441902, Cesium Carbonate, soluble in?
According to the Merck Index:13th Edition this product is extremely soluble in water and alcohol. It is also soluble in ether.
What are the impurities present in Product 441902, Cesium Carbonate?
We have performed any impurity profiling or testing on this product. However, it has been noted that some of the trace metallic impurities could include, but are not limited to, the following: Lithium, Sodium, Potassium, Rubidium, Aluminum, Barium, Calcium, Chromium, Iron, Magnesium, Nickel, and Silicon.
Product 441902, Cesium Carbonate, is very hygroscopic, how should it be handled in order to preserve the compound?
When we package this product, it is packaged and sealed under a total nitrogen atmosphere to avoid any absorption of water from the atmosphere. It would be optimal to do the same. If you do not have a glove box or glove bagwe do offer Aldrich Atmosbags that can used to help provide an inert atmosphere for compounds such as Cesium Carbonate.One could also flush the head space of the bottle before sealing it to help prevent the material from absorbing moisture during storage.
How do I find price and availability?
There are several ways to find pricing and availability for our products.Once you log onto our website, you will find the price and availability displayed on the product detail page.You can contact any of our Customer Sales and Service offices to receive a quote. USA customers: 1-800-325-3010 orview local office numbers.
What is the Department of Transportation shipping information for this product?
Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.
My question is not addressed here, how can I contact Technical Service for assistance?
Ask a Scientist here.
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Protocols & Articles

Articles

A Bulky Biaryl Phosphine Ligand Allows for Palladium-Catalyzed Amidation of Five-Membered Heterocycles as Electrophiles

The palladium-catalyzed cascade reaction of 2-chloroaryl sulfonates with arylamine and amide nucleophiles provides direct access to�N-arylbenzimidazoles. This strategy selectively produces the hetero...
Keywords: Catalysis, Chromatography, Column chromatography, Mass spectrometry, Oxidative additions

A Convenient and Expeditious Synthesis of 3-(N-Substituted) Aminocoumarins via Palladium-Catalyzed Buchwald-Hartwig Coupling Reaction

Decarboxylative coupling of sp-sp2 carbons is possible by palladium catalyst. Employing propiolic acid as a difunctional alkyne, and using the consecutive reactions of the Sonogashira reaction and th...
Keywords: Chromatography, Flash chromatography

A Single Phosphine Ligand Allows Palladium-Catalyzed Intermolecular C-O Bond Formation with Secondary and Primary Alcohols-

The substrate scope of the copper-free Sonogashira coupling has been successfully extended to cyclopropyl iodides, allowing an efficient access to a wide variety of functionalized alkynyl cyclopropan...
Keywords: Chromatography, Flash chromatography, Nuclear magnetic resonance spectroscopy, Purification, Sonogashira Coupling, Spectroscopy

AISF: A Stable, Solid Alternative to Sulfuryl Fluoride Gas

Fluorosulfates and sulfamoyl fluorides have applications ranging from chemical biology to polymer chemistry in addition to being valuable synthetic precursors to diaryl sulfates, sulfamides and sulfa...
Keywords: Chemical biology, Chromatography, Flash chromatography, Polymer science

BrettPhos Ligand Supported Palladium-Catalyzed C-O Bond Formation through an Electronic Pathway of Reductive Elimination: Fluoroalkoxylation of Activated Aryl Halides

A Pd/N-heterocyclic carbene-based catalyst achieves the Sonogashira coupling of an array of functionalized, ?-hydrogen-containing alkyl bromides and iodides under mild conditions. By furnishing the f...
Keywords: Chromatography, Cross couplings, Flash chromatography, Ligands, Sonogashira Coupling

C-O Cross-Coupling of Activated Aryl and Heteroaryl Halides with Aliphatic Alcohols-

We report an unprecedented BrettPhos ligand supported Pd-catalyzed C-O bond-forming reaction of activated aryl halides with primary fluoroalkyl alcohols. We demonstrate that the Phosphine ligand (Bre...
Keywords: Catalysis, Eliminations, Ligands, Reductive eliminations, Thin layer chromatography

Cascade Palladium Catalysis: A Predictable and Selectable Regiocontrolled Synthesis of N-Arylbenzimidazoles

A wide-ranging study�of Suzuki reactions which use nitrogen-containing heterocycles is described (see scheme). This method is highly versatile (a single procedure was used for all substrates, includi...
Keywords: Chromatography, Column chromatography, Suzuki reactions

Heck Reaction

The Heck reaction is the palladium catalyzed cross-coupling reaction between alkenes, and aryl or vinyl halides (or triflates) to afford substituted alkenes.1,2 It is a useful carbon–carbon bond form...
Keywords: Asymmetric synthesis, Cancer, Catalysis, Coupling reactions, Cross couplings, Heck Reaction, Herbicides, Ligands, Organic synthesis, Solvents

Palladium-Catalyzed Reaction of Aryl Iodides with ortho- Bromoanilines and Norbornene/Norbornadiene: Unexpected Formation of Dibenzoazepine Derivatives-

The cross-coupling reaction of aryl bromides and iodides with aliphatic and aromatic thiols catalyzed by palladium complexes of the bisphosphine ligand CyPF-tBu (1) is reported. Reactions occur in ex...
Keywords: Catalysis, Chromatography, Column chromatography, Coupling reactions, Cross couplings, Gas chromatography, Ligands, Solvents

Palladium-catalyzed coupling of functionalized primary and secondary amines with aryl and heteroaryl halides: two ligands suffice in most cases

We report our studies on the use of two catalyst systems, based on the ligands BrettPhos and RuPhos, which provide the widest scope for Pd-catalyzed C-N cross-coupling reactions to date. Often low ca...
Keywords: Arylations, Catalysis, Coupling reactions, Cross couplings, Ligands, Pharmaceutical

Properties and Applications of Functionalized Graphene Oxide

1Claremont University, Keck Graduate Institute, School of Applied Life Sciences Claremont, CA 91711, USA 2Keck Science Department, Claremont McKenna College, Claremont, CA, 91711, USA 3Keck Science D...
Keywords: Adsorption, Amidations, Antibiotics, Antimicrobials, Bacterial conjugations, Cancer, Catalysis, Cell culture, Centrifugation, Clinical, Derivatizations, Detection methods, Diagnostic, Environmental, Esterifications, Filtration, Gas chromatography, Nanoelectronics, Nanomaterials, Nucleic acid denaturation, Nucleic acid hybridization, Nucleophilic additions, Oxidations, Polymerization reactions, Purification, Redox Reactions, Reductions, SN2 reaction, Semiconductor, Separation, Solar cells, Solvents, transformation

Suzuki-Miyaura Cross-Coupling of Potassium Dioxolanylethyltrifluoroborate and Aryl/Heteroaryl Chlorides

A robust and general catalyst system�facilitates the alkoxylation of activated heteroaryl halides with primary, secondary, and select tertiary alcohols without the need for an excess of either coupli...
Keywords: High performance liquid chromatography, Liquid chromatography mass spectrometry, Purification

Suzuki-Miyaura Cross-Coupling of Potassium Trifluoro(N-methylheteroaryl)borates with Aryl and Heteroaryl Halides

A new bulky biarylphosphine ligand (L8) has been developed that allows the Pd-catalyzed C-O cross-coupling of a wide range of aryl halides and phenols under milder conditions than previously possible...
Keywords: Catalysis, Chromatography, Cross couplings, Flash chromatography, Ligands

Synthesis and Application of Palladium Precatalysts that Accommodate Extremely Bulky Di-tert-butylphosphino Biaryl Ligands

An umpolung approach to the synthesis of diaryl ketones has been developed based on in situ generation of acyl anion equivalents and their catalytic arylation. This method entails the base-promoted, ...
Keywords: Arylations, Catalysis, Chromatography, Cross couplings, Flash chromatography

The First Applications of Carbene Ligands in Cross-Couplings of Alkyl Electrophiles: Sonogashira Reactions of Unactivated Alkyl Bromides and Iodides

The synthesis of ?,?-alkynyl esters and amides using air-stable potassium alkynyltrifluoroborates as nucleophilic partners in a mild Suzuki-Miyaura cross-coupling reaction has been achieved. Propargy...
Keywords: Chromatography, Column chromatography, Coupling reactions, Cross couplings

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Peer-Reviewed Papers
15

References

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