Cesium carbonate

• Catalog No.: 12887
• CAS Number: 534-17-8
• M. F.: CCs2O3
• M. W.: 325.8198
• Purity: 99% (metals basis)

SYNONYMS

• Title: 碳酸铯
• IUPAC name: dicaesium(1+) ion carbonate
• IUPAC Traditional name: dicaesium(1+) ion carbonate

DATABASE IDS

• Beilstein Number: 4546405
• EC Number: 208-591-9
• MDL Number: MFCD00010957
• CAS Number: 534-17-8
• Merck Index: 142010

PROPERTIES

• Purity: 99% (metals basis)
• Apperance: Powder/Granules
• Density: 4.072
• Melting Point: 610°C dec.
• Solubility: Very soluble in water and alcohol. Soluble in ether
• GHS Hazard statements: H315-H319-H335-H303
• European Hazard Symbols: Irritant (Xi)
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Risk Statements: 36/37/38
• RTECS: FK9400000
• Safety Statements: 26-37
• Storage Warning: Hygroscopic
• TSCA Listed: 是

REFERENCES

• Can be used to prepare Cs salts of N-protected amino acids or peptides, which can then be cleanly esterified by treatment with an alkyl halide in DMF: Helv. Chim. Acta, 56, 1476 (1973); J. Org. Chem., 42, 1286 (1977). Carboxylic acids can be esterified in high yield with an alkyl halide and Cs₂CO₃ at ambient temperature in DMF: Synth. Commun., 30, 2687 (2000). Benzoic acids can be esterified by refluxing with an alcohol in acetonitrile: Org. Prep. Proced. Int., 28, 480 (1996).
• The di-Cs salts of catechol and resorcinol are superior to other alkali metal salts in the reaction with dibromoethers in DMF to give crown ethers: J. Chem. Soc., Chem. Commun., 285 (1979). Also used in the facile synthesis of alkyl phenyl ethers from phenols and alkyl halides in acetonitrile: Synth. Commun., 25, 1367 (1995), and catalytically in the O-methylation of phenols by heating in excess dimethyl carbonate: Synlett, 1063 (1998); K₂CO₃ was found to be less effective. Indoles undergo N-alkylation in DMPU: Synlett, 2394 (2004).
• For use in formation of macrocyclic sulfides from dithiols and dibromoalkanes, see: J. Org. Chem., 46, 4481 (1981); Org. Synth. Coll., 8, 592 (1993). Salts of other metals are ineffective.
• For a review of the 'cesium ion effect' and macrocyclization, see: Org. Prep. Proced. Int., 24, 285 (1992).
• Superior base for Horner-Wadsworth-Emmons olefination reaction of phosphonates: Chem. Lett., 335 (1989); Bull. Soc. Chim. Belg., 100, 267 (1991).
• For cleavage of 2-oxazolidinones to give amino alcohols, see: Tetrahedron Lett., 28, 4185 (1987).
• For a brief feature on uses of the reagent in synthesis, see: Synlett, 2447 (2004).