Fluoro-acetic acid

It will readily be seen in our series of w-fluorocarboxylic acids, that when n is odd, / -oxidation would yield the toxic fluoro-acetic acid, whereas when n is even, the compound would presumably be oxidized only as far as the non-toxic yff-fluoro-propionic acid.1 The pharmacological results obtained are in complete accord with this hypothesis, and provide verification, of a kind not hitherto achieved, of the process of / -oxidation in the living animal body. However, Weinhouse, Medes and Floyd2 have inoculated rat-liver slices with one or two fatty acids containing isotopic carbon, and have obtained some evidence for a process of /7-oxidation. 

The toxicity of the acaricide 2-fluoro-A-methyl-A-(naphth-l-yl)acet-amide (MNFA) (4.152) to mammals is related to its hydrolysis. In this case, however, toxicity was mainly due to the acid formed. Indeed, the 2-fluoro-acetic acid (4.153) liberated by hydrolysis was further metabolized to fluoro-citrate, which inhibits the tricarboxylic acid cycle [101]. 

Oxidation of primary amino group in aromatic compounds by peroxytri-fluoro acetic acid has been reported by Clarke and Steele [69]. The yield was... 

The very high toxicity of ethyl 5-fluoropentanecarboxylate and its derivatives and the fluoroacetate-like symptoms produced seemed to us to be of particular interest, since by a process of ) -oxidation in the animal body 5-fluoropentanecarboxyhc acid would readily give rise to the toxic fluoroacetic acid. Similar remarks apply to y-fluorobutyric acid and its derivatives prepared independently by American workers. The non-toxicity of y -fluoropropionic acid and its derivatives may, on the other hand, be due to the inability of this acid to give the toxic fluoro-acetic acid by a process of yff-oxidation. 

Fig. 9 36. Hydrogen bonding patterns in the crystal structures of acetic acid and its halo derivatives, (a) acetic acid, (b)fluoro acetic acid, (c) chloro acetic acid, (d) bronw acetic acid...

The quantitative and qualitative response among different species to fluoro-acetic acid is unique [115]. Lethal doses range from 50 [xg/kg in dogs to 50 mg/kg in some monkeys, while some data indicate that man is intermediate. The mouse responds like the monkey, while the cat and rabbit are nearly as sensitive as the dog. Fluoroacetate is biochemically converted into fluorocitrate, a lethal synthesis, which results in the inhibition of a step in the tricarboxylic acid cycle. Various species may die from central nervous system stimulation, others from cardiac irregularities, and others from a combination of central and cardiac effects. A simple explanation for these variations is not available. 

C3H4C1F02 chloro-fluoro-acetic acid methyl ester 433-52-3... 

C4H6C1F02 1661 C4H6C1F02 1662 C4H6C1F30 chloro-acetic acid 2-fluoro-ethyl ester chloro-fluoro-acetic acid ethyl ester 2-chloro-l-ethoxy-l,l 2-trifluoro-ethane 589-84-4 401-56-9 310-71-4... 

C4H6F2O2 fluoro-acetic acid 2-fluoro-ethyl ester 459-99-4... 

C4H7FO2 fluoro-acetic acid ethyl ester 459-72-3... 

CsHsClFOa chloro-fluoro-acetic acid propyl ester 348-70-9... 

C6H10CIFO2 chloro-fluoro-acetic acid butyl ester 368-34-3... 

C4 H6 Cl F 02 chloro-fluoro-acetic acid ethyl ester 401-56-9 RI Temp/C Lambda/nm Ref. 

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