Cesium carbonate, 99% (metals basis)
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Pricing and Availability
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|Form:||Powder/Granules||Solubility:||Very soluble in water and alcohol. Soluble in ether|
|Melting point:||610° dec.|
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).
|Harmonized Tariff Code:||2836.99|
GHS Hazard and Precautionary Statements
Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation. May be harmful if swallowed.
Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.
Risk & Safety
|Irritating to eyes, respiratory system and skin.|
|In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Wear suitable gloves. This material and/or its container must be disposed of as hazardous waste.|