Highly-toxic fluorine compounds

Fluoroalkene chemistry

“…4 The result is useful from a synthetic viewpoint, vinyl sulfide 7 (1674 cm À1 ) made by treating HFCB with 2,6-dimethoxybenzenethiol is isomeric with allyl sulfide 9 (1784 cm À1 ) which displays a C¼C stretch close to that for HFCB (1798 cm À1 ) and for 3-Cl (1795 cm À1 ) confirming that the arylthio group is not attached to the double bond.…”

“…Further evidence that biological activity correlates with fluorocycloalkene reactivity was provided by a study of the effect of ring size on toxicity. It was found that inhalation toxicity to mice decreased in the order perfluorocyclopropene > HFCB > perfluorocyclopentene [4]. Perfluorocyclopropene is the most toxic cycloalkene examined to date, its toxicity approaching that of PFIB.…”

“…Propanethiol and N-acetylcysteine isopropyl ester, with accessible SH groups, have reactivities comparable to those of the lung thiols cysteine and glutathione. 2 Steric hindrance of the thiol Table 1 Inhalation toxicities of fluorobutene analogues in mice and rats [4,25] Fluorobutene Designation LCt 50 mice a (mg min m À3 ) LCt 50 rats a (mg min m À3 ) The LCt 50 is the lethal concentration that kills 50% of a group of animals and is expressed in milligrams of fluoroalkene per metre cubed multiplied by the exposure time t in minutes (mg min m À3 ). It is based on deaths occurring up to 14 days following exposures of 10 min duration.…”

“…Many monofluorinated compounds are highly toxic by metabolism to 2R,3R-2-fluorocitrate or by inhibition of the enzyme acetylcholinesterase, but some polyfluorinated materials such as highly fluorinated alkenes are also poisonous [1][2][3][4]. One of the most toxic is perfluoroisobutene (PFIB), 1 a by-product of Teflon TM manufacture whose toxicity is legendary [8][9][10][11][12][13][14].…”

Evidence of VX nerve agent use from contaminated white mustard plants

“…Combining GC and LC-MS methods extends the range of analytes detectable in a single sample. Besides sarin (isopropyl methylphosphonofluoridate) and soman (pinacolyl methylphosphonofluoridate) [9], one of the most hazardous nerve agents is VX (O-ethyl S-2-diisopropylaminoethyl methylphosphonothiolate) [10]. These agents react with moisture to give respectively the alkyl methylphosphonic acids: isopropyl methylphosphonic acid (iPMPA), pinacolyl methylphosphonic acid (PMPA) and ethyl methylphosphonic acid (EMPA) [11][12][13] and more slowly, methylphosphonic acid (MPA) [14,15] (figure 1).…”