Chlorothioformic acid chloride

Graubaum et al. studied the reaction of 5-aminothiatriazole (10) with chloroformates in the presence of base and isolated 1,2,4-thiadiazoles (104 R = OR) <89M997, 90JPR208). In the reaction between 5-aminothiatriazole and chlorothioformates in the presence of base the main products were trithiapentalenes (116) (Scheme 21). However, in the absence of base the intermediary 5-alkoxy-and 5-aryloxy-3-imino-A -1,2,4-dithiazoline (115) hydrochlorides are isolated. These reactions are analogous to those of (10) and acid chlorides (Section 4.19.6.1.2). 

Graubaum and co-workers described the reactions of chlorothioformates 102 with 5-aminothiatriazole 90. Depending on the reaction conditions different products are formed. In the presence of a base, the main product is the trithiadiazapentalene 101, but in the absence of a base the dithiazolinimine hydrochlorides 100 are obtained (Scheme 23) <1989M997, 1990JPR208>. Thus, the reactivity of chlorothioformates is intermediate between that of acid chlorides and imidoyl chlorides. 

Carbonoohloridothioic acid, S-ethyl ester CCRIS 4642 EINECS 220-928-1 Ethyl chlorothioformate Ethyl thiochloroformate Ethylthiooarbonyl chloride Ethylthiol chloroformate Formic acid, chlorothio-, S-ethyl ester HSDB 5906 S-(Ethyl)chlorothioformic acid S-Ethyl carbonochloridothioate S-Ethyl chlorothiocarbonate UN2826,... 

ETHYL CHLOROTHIOFORMATE (2941-64-2) Forms explosive mixture with air (flash point 86°F/19°C). Reacts with moisture in air, forming hydrogen chloride fumes. Reacts slowly with water or steam, forming hydrochloric acid, carbon dioxide gas, and ethanol. Violent reaction with alkali metals, dialkylzincs, dimethyl formamide, dimethyl sulfoxide, ethers, ethylene glycol diethyl ether, strong oxidizers. Incompatible with strong bases. Corrodes metals in the presence of moisture. Attacks some plastics, rubber, and coatings. 

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