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Description
TCI Cesium Carbonate, catalog code C2160, is an inorganic salt of the alkali metal cesium that has become one of the most popular bases in modern organic synthesis. In the laboratory this compound is used primarily as a proton-scavenging base in alkylation reactions, transition-metal-catalyzed cross-coupling reactions, and nucleophilic aromatic substitution reactions. Its presence on the reagent shelf of a synthesis laboratory means that many transformations that previously proceeded only with difficulty under conventional bases can now be carried out under considerably milder conditions.
The property that most often leads chemists to select cesium carbonate is its relatively good solubility in polar aprotic organic solvents such as DMF, DMSO, and acetonitrile, far exceeding that of the corresponding potassium or sodium carbonate salts. The cesium cation is large and has low polarizing power, so its ion pairing is loose; this leaves the accompanying nucleophilic anion more reactive, an effect widely known as the cesium effect. Its basicity is moderate, strong enough to deprotonate phenols, thiols, amides, or dicarbonyl compounds, yet mild enough to leave sensitive functional groups intact. The compound is also hygroscopic, which must be taken into account during handling.
In Indonesian laboratories, this reagent is typically found in university organic synthesis and medicinal chemistry groups, in research institute laboratories, and in pharmaceutical and fine chemical development units where coupling and alkylation reactions are run routinely. Because the local climate is humid throughout the year, laboratories here pay particular attention to keeping the container tightly closed and limiting exposure to open air, so that the reagent retains its performance from one experiment to the next.
Laboratory Applications
- Alkylation of phenols and thiols — the moderate basicity deprotonates these substrates cleanly while the loose cesium ion pair keeps the resulting anion highly nucleophilic toward the alkylating agent.
- Transition-metal-catalyzed cross-coupling reactions — serves as the proton-scavenging base that keeps the catalytic cycle turning over without attacking sensitive functional groups elsewhere in the substrate.
- Nucleophilic aromatic substitution — good solubility in DMF, DMSO, and acetonitrile allows the base to work in the homogeneous polar aprotic media these substitutions normally require.
- N-alkylation of amides and related nitrogen nucleophiles — basicity sufficient to deprotonate the amide nitrogen while remaining mild enough to preserve other functionality in the molecule.
- Deprotonation and functionalization of dicarbonyl compounds — generates the stabilized enolate under milder conditions than conventional carbonate bases permit, which is useful for multi-step synthetic sequences.
Specifications
- Brand: TCI
- CAS number: 534-17-8
- Catalog code: C2160
- Category: Chemistry > Catalysis and Inorganic Chemistry > Main-group Elements [Catalysis and Inorganic Chemistry]
- Chemical class: inorganic alkali metal salt (cesium carbonate)
- Storage note: hygroscopic material; keep the container tightly closed and protected from moisture. Pack sizes available on request.
Handling and Storage
Store cesium carbonate in its original tightly closed container, in a dry place away from direct exposure to humid air, since the material is hygroscopic and readily takes up atmospheric moisture. Chemically resistant containers with well-sealed caps are appropriate, and transferring the reagent inside a glove box or under a dry inert atmosphere is advisable when reaction results are sensitive to water content. Weigh out only the quantity needed and close the container immediately afterwards. Handle the material in a fume hood using safety glasses, gloves, and a laboratory coat, avoid contact with skin and eyes and inhalation of the dust, and consult the manufacturer's safety data sheet before use.
