Sodium fluoroacetamide

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). 

Fluoroacetyl chloride, CH2FCOCl, was prepared by the action of phosphorus pentachloride on the free fluoroacetic acid (p. 121).1 It is extremely useful as fluoroacetylating agent in synthetic work. Because of its importance we have recently reinvestigated other methods of preparation.2 These may be summarized as follows (1) direct from fluoroacetamide (p. 125) by the action of phosphorus oxychloride and water (2) the action of phosphorus oxychloride on either sodium fluoroacetate (p. 121) or on barium fluoroacetate (p. 121). Good yields are obtained in both (1) and (2), and in each case the starting materials are more easily available than fluoroacetic acid itself. 

Class B Fluoroacetic acid and salts, e.g. sodium fluoroacetate, triethyl-lead fluoroacetate all simple esters of fluoroacetic acid fluoroacetamide and substituted amides fluoroacetamidine hydrochloride fluoroacetyl chloride and fluoride fluoro-ethanol and its simple esters fluoroacetaldehyde. 

Standardization, of the sodium peroxide bomb method with pure fluoroacetamide... 

Toxicity. Fluoroacetamide is extremely toxic to animals and man but its lethal action is slower than sodium fluoroacetate. 

Egyed, M.N., Shlosherg, A. (1973). Diagnosis of field cases of sodium fiuoroacetate and fluoroacetamide poisoning in animals. Ref. Vet. 30 112-15. 

Under certain conditions the reduction of amides leads to primary alcohols (cf. method 428). Thus, phenylethylacetamide is reduced by sodium and absolute ethanol to 2-phenyl-1-butanol (75%). a-Naphthylacetamide is reduced by sodium amalgam and hydrochloric acid to a-naphthylcarbinol (63%). Trifluoroethanol is obtained by catalytic hydrogenation of tri-fluoroacetamide over a platinum catalyst. Hydrogenation of the corresponding ester over copper-chromium oxide failed. ... 

The amide of fluoroacetate, fluoroacetamide (4) is a rodenticide with similar properties (Chapman and Phillips, 1955). Its toxicity to mammals is somewhat lower than that of sodium fluoroacetate, and it is probably safer to handle. 

Red squill (Drimia maritime, Asparagaceae), strychnine Fluoroacetamide, sodium fluoroacetate, zinc phosphide, sodium norbormide... 

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

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