세슘 탄소산

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세슘 탄소산 MSDS

Cesium carbonate

세슘 탄소산 C화학적 특성, 용도, 생산

물성

610℃-dec。

물성

고체(흰색)。

물성

610℃-dec。

개요

Cesium carbonate is a basic carbonate and is used in organic synthesis as a mild inorganic base. It can be used in C, N, O alkylation and arylation reactions. Cesium carbonate not only promotes the carbonylation of alcohols and carbamination of amines but also inhibits side reactions common in other processes. It is also used in six-membered annulation, intramolecular and intermolecular cyclizations, Suzuki coupling, aza-Henry, nucleophilic substitution, cross-coupling and different cycloaddition reactions.

화학적 성질

Colourless crystals or white powder , easily soluble in water, quickly absorbs moisture when placed in the air. The aqueous solution of cesium carbonate is strongly alkaline and can react with acid to produce the corresponding cesium salt and water, and release carbon dioxide.

용도

Cesium carbonate is a versatile reagent for organic synthesis. This inorganic base has been employed in numerous organic applications ranging from N-protection of amino acids to a base in either the Horner- Wadsworth-Emmons reaction or in Suzuki couplings. It has also found use as a catalyst for ethylene oxide polymerization, in coating for spatter-free welding of steel in CO2, as a functional interlayer in photovoltaic devices and in oxide cathodes. Cesium carbonate is also used in the beer-brewing industry to make the "head" of beer foamier.

제조 방법

cesium carbonate can be prepared by thermal decomposition of caesium oxalate. Upon heating, caesium oxalate is converted to caesium carbonate with emission of carbon monoxide.
Cs2C2O4 → Cs2CO3 + CO
It can also be synthesized by reacting caesium hydroxide with carbon dioxide.
2 CsOH + CO2 → Cs2CO3 + H2O

주요 응용

Cesium carbonate is widely utilized as a precursor for other cesium compounds. It acts as a base in sensitive organic reactions. It can be used as a base in C-C and C-N cross-coupling reactions such as SuzukiMiyaura, Heck, and Buchwald-Hartwig amination reactions. It finds use in solar cells as it increases the power conversion efficiency of cells through the transfer of electrons. It is also used in the production of special optical glasses, petroleum catalytic additives, special ceramics and in the sulfuric acid industry. It is useful in the N-alkylation (of sulfonamides, beta-lactams, indoles, heterocycles and several sensitive nitrogen compounds), carbamination of amines, carbonylation of alcohols and aerobic oxidation of alcohols into carbonyl compounds without polymeric by products. Promotes the efficient O-alkylation of alcohols to form mixed alkyl carbonates.

화학 반응

The numerous properties of caesium carbonate in organic synthesis stem from the relatively weak Lewis acidity of the caesium ion, enabling its solubility in organic solvents such as alcohols, DMF, and diethyl ether. Caesium carbonate serves as an effective inorganic base in numerous palladium-catalysed reactions, including the Heck, Suzuki, and Sonogashira reactions. As shown in Equation 1 [1], the Suzuki cross-coupling reaction achieves an 86% yield when facilitated by caesium carbonate. However, the same reaction yields only 29% and 50% when using sodium carbonate or triethylamine, respectively. In the Heck reaction between methacrylates and chlorobenzene, caesium carbonate demonstrates markedly superior performance compared to other inorganic bases (e.g., potassium carbonate, sodium acetate, triethylamine, potassium phosphate) (Equation 2 [2]).

일반 설명

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.

위험도

Cesium carbonate is a danger compound.
H315: Causes skin irritation
H318: Causes serious eye damage
H335: May cause respiratory irritation
H361: Suspected of damaging fertility or the unborn child
H373: May cause damage to organs through prolonged or repeated exposure

Safety Profile

Moderately toxic by ingestion. Mutation data reported. When heated to decomposition it emits acrid smoke and fumes. See also CESIUM.

Purification Methods

Crystallise it from ethanol (10mL/g) by partial evaporation. [D.nges in Handbook of Preparative Inorganic Chemistry (Ed. Brauer) Academic Press Vol I p 988 1963.]

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