Trichloroacetic acid
Trichloroacetic acid (TCA; TCAA; also known as trichloroethanoic acid) is an analogue of acetic acid in which the three hydrogen atoms of the methyl group have all been replaced by chlorine atoms. Salts and esters of trichloroacetic acid are called trichloroacetates.
Trichloroacetic acid
C2HCl3O2
Molar mass 163.38 g·mol−1
Appearance Colorless to white, crystalline solid Odorsharp, pungent
Density 1.63 g/cm3
Melting point 57 to 58 °C (135 to 136 °F; 330 to 331 K)
Boiling point 196 to 197 °C (385 to 387 °F; 469 to 470 K)
Soluble in 0.1 parts[2]Vapor pressure1 mmHg (51.1°C)
Acidity (pKa)
0.66
It is prepared by the reaction of chlorine with acetic acid in the presence of a suitable catalyst.
CH
3COOH + 3Cl
2 → CCl
3COOH +3HCl
Another route to trichloroacetic acid is the oxidation of trichloroacetaldehyde.
It is widely used in biochemistry for the precipitation of macromolecules, such as proteins, DNA, and RNA. TCA and DCA are both used in cosmetic treatments (such as chemical peels and tattoo removal) and as topical medication for chemoablation of warts, including genital warts. It can kill normal cells as well. It is considered safe for use for this purpose during pregnancy.
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