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Sodium trichloroacetate
Chemical compound From Wikipedia, the free encyclopedia
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Sodium trichloroacetate is a chemical compound with a formula of CCl3CO2Na. It is used to increase sensitivity and precision during transcript mapping.[1] It was previously used as an herbicide starting in the 1950s but regulators removed it from the market in the late 1980s and early 1990s.[2][3][4][5]
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Preparation
Sodium trichloroacetate is made by reaction trichloroacetic acid with sodium hydroxide:
- CCl3CO2H + NaOH → CCl3CO2Na + H2O
Reactions
Basicity
Sodium trichloroacetate is a weaker base than sodium acetate because of the electron-withdrawing nature of the trichloromethyl group. Sodium trifluoroacetate is likewise a weaker base. However, it can easily be protonated in the presence of suitably strong acids:
- CCl3CO−2 + H2SO4 → CCl3CO2H + HSO−4
Trichloromethyl-anion precursor
This reagent is useful for introducing the trichloromethyl group into other molecules. Decarboxylation produces the trichloromethyl anion, which is a sufficiently strong nucleophile to attack various carbonyl functional groups, such as aldehydes, carboxylic acid anhydrides,[6] ketones (making a precursor for the Jocic–Reeve reaction), and acyl halides.
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See also
References
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