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Trichloroacetic acid

Trichloroacetic acid



IUPAC name	Trichloroacetic acid
Identifiers
CAS number	76-03-9
RTECS number	AJ7875000
SMILES	ClC(Cl)(Cl)C(O)=O
Properties
Molecular formula	CCl₃COOH
Molar mass	163.4 g/mol
Appearance	white solid
Density	1.63 g/cm³, solid
Melting point	57 °C
Boiling point	196 °C
Solubility in water	very good
Acidity (pK_a)	0.77
Structure
Dipole moment	3.23 D
Hazards
EU classification	Corrosive C) Dangerous for the environment (N)
R-phrases	R35, R50/53
S-phrases	(S1/2), S26, S36/37/39, S45, S60, S61
Related Compounds
Related chloroacetic acids	Chloroacetic acid Dichloroacetic acid
Related compounds	Acetic acid Trifluoroacetic acid Tribromoacetic acid
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Trichloroacetic acid (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as trichloroethanoic acid) is an analogue of acetic acid in which the three hydrogen atoms of the methyl group have all been replaced by chlorine atoms. It is a strong acid, comparable to sulfuric acid.

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It is prepared by the reaction of chlorine with acetic acid in the presence of a suitable catalyst.

CH₃COOH + 3Cl₂ → CCl₃COOH + 3HCl

It is widely used in biochemistry for the precipitation of macromolecules such as proteins, DNA and RNA. Its sodium salt is used as a weedkiller. Solutions containing trichloroacetic acid as an ingredient are used for tattoo removal and the treatment of warts, including genital warts. It is considered safe for use for this purpose during pregnancy^[1].

Salts of trichloroacetic acid are called trichloroacetates. Reduction of trichloroacetic acid results in dichloroacetic acid, a pharmacologically active compound that shows promise for the treatment of cancer^[2].

History

The discovery of trichloroacetic acid by Jean-Baptiste Dumas in 1840 delivered a striking example to the slowly evolving theory of organic radicals and valences.^[3] The theory was contrary to the beliefs of Jöns Jakob Berzelius, starting a long dispute between Dumas and Berzelius.^[4]

References

^ Wiley DJ, et al. (2002). External genital warts: Diagnosis, treatment, and prevention. Clinical Infectious Diseases, 35(Suppl 2): S210–S224
^ The Carcinogenic Potency Database (CPDB)
^ Dumas (1840). "Trichloroacetic acid". Annalen der Chemie XXXII: 101.
^ William Albert Noyes (1927). "Valence". Proceedings of the American Philosophical Society 66: 287-308.