Monofluoroacetic acid

Health and Safety Factors. Completely fluorinated alkanes are essentially nontoxic (16). Rats exposed for four hours to 80% perfluorocyclobutane and 20% oxygen showed only slight effects on respiration, but no pathological changes in organs. However, some fluorochemicals, especially functionalized derivatives and fluoroolefins, can be lethal. Monofluoroacetic acid and perfluoroisobutylene [382-21-8] are notoriously toxic (16). 

Hydrofluorocarbons generally are less toxic than HGFGs, with the notable exception of HFG-152, GH2FGH2F, which apparently can be metabohcaHy converted to monofluoroacetic acid and is therefore quite toxic (44). 

Monofluoroacetic acid offers little promise as a mosquito larvicide, but 2-ethylhexyl monofluoroacetate is a very powerful aphicide. The high toxicity of the fluorinated lower aliphatic acids and their esters to vertebrates probably precludes their use as insecticides except under highly controlled conditions. The toxicity of the fluorinated acids to the vertebrates is attributed to their interference with an enzyme system, but the possibility of finding one with a high specificity for insects is not excluded. 

Chenoweth, M.B. 1949. Monofluoroacetic acid and related compounds. Pharmacol. Rev. 1 383424. 

Kun, E. 1982. Monofluoroacetic acid (compound 1080), its pharmacology and toxicology. Pages 34-41 in R.E. Marsh (ed.). Proceedings Tenth Vertebrate Pest Conference. Univ. California, Davis, CA. 

The only monofluorinated synthons that are available are monofluoroacetic acid and its derivatives (esters, thioacetate, bromofluoroacetate) and halogenofluoromethanes (CHCI2F). 

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

Esters of chlorodifluoroacetic acids, like the esters of monofluoroacetic acid, can acylate anions (e.g., organometallic derivatives, enolates, lithiated sulfones). They lead to chlorodifluoromethylketones and to S-ketosulfones and jS-ketoesters which have the —CFj motif (Figure 2.16). ... 

Monofluoroacetic acid (fluoroacetate) (Fig. 7.61) is a compound found naturally in certain South African plants, which causes severe toxicity in animals eating such plants. The compound has also been used as a rodenticide. The toxicity of fluoroacetate was one of the first to be studied at a basic biochemical level, and Peters coined the term "lethal synthesis" to describe this biochemical lesion. 

CH2FCOOH (c). Swarts4 (see Kharasch1) measured the heat of combustion of monofluoroacetic acid. 

Carboxylic acids contain the -C(0)0H functional group bound to an aliphatic, olefinic, or aromatic hydrocarbon moiety. This section deals with those carboxylic acids that contain only C, H, and O. Carboxylic acids that contain other elements, such as trichloroacetic acid (a strong acid) or deadly poisonous monofluoroacetic acid, are discussed in later chapters. Some of the more significant carboxylic acids are shown in Figure 14.6. 

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. 

PROP The potassium salt of monofluoroacetic acid was once designated as potassium cymonate. 

Monofluoroacetic acid is even more toxic than MCA, being fatal after ingested doses of 2 mg/kg whereas MCA is fatal after doses of 50 mg/kg. ... 

Fluoroacetate (3), the sodium salt of monofluoroacetic acid, is also a substance of vegetable origin, reported to poison sheep and cattle repeatedly. It is the toxic substance of a South African plant called gifblaar (Dichapetalum cymostm) and of the Australian plant Acacia georginae (Marais, 1944). The compound is readily soluble in water and is very toxic. Its acute oral lDj for rats is 0.2-2 mg/kg. The compound is converted via the citrate cycle into fluorocitrate and this blocks the citrate cycle. 

Chbnowbth, M. B. (1949). Review of Monofluoroacetic Acid and Related Compounda, in Pharmacol. 97, 383. 

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