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Trichloroacetic acid
From Wikipedia, the free encyclopedia
| Trichloroacetic acid | |
|---|---|
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| General | |
| IUPAC name | Trichloroacetic acid |
| Systematic name | Trichloroethanoic acid |
| Molecular formula | CCl3COOH |
| SMILES | ClC(Cl)(Cl)C(O)=O |
| Molar mass | 163.4 g/mol |
| Appearance | white solid |
| CAS number | [76-03-9] |
| Properties | |
| Density and phase | 1.63 g/cm3, solid |
| Solubility in water | very good |
| Melting point | 57 °C |
| Boiling point | 196 °C |
| Acidity (pKa) | 0.77 |
| Dipole moment | ? D |
| Hazards | |
| MSDS | External MSDS |
| EU classification | Corrosive C) Dangerous for the environment (N) |
| NFPA 704 | |
| R-phrases | R35, R50/53 |
| S-phrases | S1/2, S26, S36/37/39, S45, S60, S61 |
| Flash point | ? °C |
| RTECS number | AJ7875000 |
| Supplementary data page | |
| Structure and properties |
n, εr, etc. |
| Thermodynamic data |
Phase behaviour Solid, liquid, gas |
| Spectral data | UV, IR, NMR, MS |
| 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as trichloroethanoic acid) is an analogue of acetic acid in which the three hydrogen atoms of the methyl group have all been replaced by chlorine atoms.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 a strong acid, comparable to sulfuric acid.
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.
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.
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The discovery of trichloracetic acid by Jean-Baptiste Dumas in 1840 delivered a striking example to the slowly evolving theory of organic radicals and valences.[1] The theory was contrary to the beliefs of Jöns Jakob Berzelius, starting a long dispute between Dumas and Berzelius.[2]
- ^ Dumas (1840). "Trichloroacetic acid". Annalen der Chemie XXXII: 101.
- ^ William Albert Noyes (1927). "Valence". Proceedings of the American Philosophical Society 66: 287-308.