From Monofluoroacetic Acid

3 Compounds Derived from Fluoroacetic Acids 11.3.1 From Monofluoroacetic Acid 

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Figure 2.7 Reaction of enolates of esters derived from monofluoroacetic acid. ...

Compounds Derived from Fluoroacetic Adds [5958] p. 1264 11.3.1 From Monofluoroacetic Acid [5958] p. 1264... 

Esters of monofluoroacetic acid, e.g. 1" and 2, are synthesized from the corresponding chloro or bromo derivatives with potassium fluoride." The yield for the synthesis of ethyl fluoroacetaie (1) ranges from 20 to 75%. Similarly, chloroacetamide and chloroacetonitrile... 

De Oliveira, M.M. (1963). Chromatographic isolation of monofluoroacetic acid from Palicourea marcgravii. Experientia 19 586-7. 

Among the most deadly of simple compounds is sodium fluoroacetate. The LD50 (the dose lethal for 50% of animals receiving it) is only 0.2 mg/kg for rats, over tenfold less than that of the nerve poison diisopropylphosphofluoridate (Chapter 12).a b Popular, but controversial, as the rodent poison "1080," fluoroacetate is also found in the leaves of several poisonous plants in Africa, Australia, and South America. Surprisingly, difluoroacetate HCF2-COO is nontoxic and biochemical studies reveal that monofluoroacetate has no toxic effect on cells until it is converted metabolically in a "lethal synthesis" to 2R,3R-2-fluorocitrate, which is a competitive inhibitor of aconitase (aconitate hydratase, Eq. 13-17).b This fact was difficult to understand since citrate formed by the reaction of fluorooxalo-acetate and acetyl-CoA has only weak inhibitory activity toward the same enzyme. Yet, it is the fluorocitrate formed from fluorooxaloacetate that contains a fluorine atom at a site that is attacked by aconitase in the citric acid cycle. 

Monofluoroacetate, a toxin from the poison leaf plant Dichapetalum cymosum, was isolated and analyzed on a specialty organic acid analysis column (2 = 210nm) using an aqueous 20 mM H3PO4 mobile phase [1580]. This compound waS well separated from formic, acetic, and propionic acids. Peak shapes were excellent and elution was complete in 35 min. Linearity was achieved over the range 25-... 

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