Trichloroacetic acid
From Wikipedia, the free encyclopedia
| Trichloroacetic acid | |
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| 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 (pKa) | 0.77[1] |
| 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 |
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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as trichloroethanoic acid) is an analogue of acetic acid in which the three hydrogen atoms of the methyl group have all been replaced by chlorine atoms.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 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 can kill normal cells as well. It is considered safe for use for this purpose during pregnancy[2].
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[3].
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[edit] 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.[4] The theory was contrary to the beliefs of Jöns Jakob Berzelius, starting a long dispute between Dumas and Berzelius.[5]
[edit] See also
[edit] References
- ^ Ionization Constants of Heteroatom Organic Acids
- ^ 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.
