Fluoroacetamide compound

Fluoroacetamide. Fluoroacetamide [640-19-7], FCH2CONH2, is a white water-soluble soHd having mp 108°C (14). It has been used as a rodenticide and has been reported to have a better acceptability to rats than sodium fluoroacetate (29). However, like the latter compound, its misuse has caused deaths to farm animals and pets (20). 

Moreover, the electrochemical fluoroacetamidation of cycloalkenes was carried out in acetonitrile with tetraethylammonium fluoride/hydrofluoric acid, in order to obtain fluoroac-etamides 16 and 17, although in low yield. cw-Compounds are the major components of the reaction mixture, as determined by H NMR. This result was ascribed to the acetonitrile addition to the /1-fluorocarbocation absorbed on the electrode surface185-186. 

CAUTION Monofluoroacetates are intermediates for some literature syntheses of fluorinated heterocycles. Fluoroacetic acid and its derivatives, such as fluoroacetamide and ethyl fluoroacetate, and compounds which could be metabolically converted into fluoroacetate, such as 2-fluoroethanol, are extremely toxic and have no antidote. A lethal dose of the acid in humans may be as low as 100 mg. They should be avoided if at all possible, but if their use is essential, they must only be used under rigorous control. 

In class B are placed all simple esters, CHjF CO i , of fluoro-aoetic acid, where iZ = Me, Et, Pr , Pr , Ph, etc. When substitution takes place in the a-hydrogen atoms, e.g. in methyl a-fluoropropionate or a-fluoroisobutyrate, then the compound is devoid of toxicity. This indicates the importance of the unsubstituted fluoromethyl group. On pp. 125 et seq. it was shown that fluoroacetamide and a variety of substituted amides such as CHjF CO NH CHg CHjCl were, molecule for molecule, equally toxic with fluoroacetic acid and produced the same symptoms. The 2 chloroethyl group therefore contributed nothing appreciable to the toxicity of the molecule. The majority of the esters of fluoroethanol showed the toxicity of the parent alcohol, e.g. 2-fluoroethyl chlorosulphonate, CHgF CHg O SOjCl, di-(2-fluoroethyl) sulphate and 2-fluoroethylglycine hydrochloride. 

VIII. Sodium fluoroacetate (compound 1080) and fluoroacetamide 289 IX. Other rodentiddes 293... 

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