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2-Fluoroethanol
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2-Fluoroethanol
2-Fluoroethanol is the organic compound with the formula CH2FCH2OH. This colorless liquid is one of the simplest stable fluorinated alcohols. It was once used as a pesticide. The related difluoro- and trifluoroethanols are far less dangerous.
2-Fluoroethanol was originally synthesized by treating 2-chloroethanol with potassium fluoride, in a simple Finkelstein reaction. The product has a lower boiling point that the starting material and may be conveniently isolated by distillation.
Similar procedures start from (1,3)-dioxolan-2-one and from 2-bromoethanol.
Hydrogen bonding stabilizes the gauche conformer.
In a basic solution, 2-fluoroethanol undergoes dehydrofluorination, giving acetaldehyde.
Reaction of 2-fluoroethanol with trifluoromethanesulfonic anhydride in the presence of base gives the triflate ester.
2-[18F]-fluoroethoxy group is a common moiety in the structures of radiotracers used with PET. Such radiotracers include fluoroethyl-l-tyrosine 1-(2-[18F]-fluoroethoxy)-4-nitrobenzene and [18F]-fluoroethyl 4-fluorobenzoate, being a [18F]fluoroalkyl ether and ester respectively.
It was patented as a rodenticide in Germany in 1935. In rats, it was found that fluoroethanol induced a similar toxicity as that of fluoroacetate, known to metabolize to fluorocitrate to exert the toxic effect.
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2-Fluoroethanol
2-Fluoroethanol is the organic compound with the formula CH2FCH2OH. This colorless liquid is one of the simplest stable fluorinated alcohols. It was once used as a pesticide. The related difluoro- and trifluoroethanols are far less dangerous.
2-Fluoroethanol was originally synthesized by treating 2-chloroethanol with potassium fluoride, in a simple Finkelstein reaction. The product has a lower boiling point that the starting material and may be conveniently isolated by distillation.
Similar procedures start from (1,3)-dioxolan-2-one and from 2-bromoethanol.
Hydrogen bonding stabilizes the gauche conformer.
In a basic solution, 2-fluoroethanol undergoes dehydrofluorination, giving acetaldehyde.
Reaction of 2-fluoroethanol with trifluoromethanesulfonic anhydride in the presence of base gives the triflate ester.
2-[18F]-fluoroethoxy group is a common moiety in the structures of radiotracers used with PET. Such radiotracers include fluoroethyl-l-tyrosine 1-(2-[18F]-fluoroethoxy)-4-nitrobenzene and [18F]-fluoroethyl 4-fluorobenzoate, being a [18F]fluoroalkyl ether and ester respectively.
It was patented as a rodenticide in Germany in 1935. In rats, it was found that fluoroethanol induced a similar toxicity as that of fluoroacetate, known to metabolize to fluorocitrate to exert the toxic effect.
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