Trichloroacetic acid
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| Names | |||
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| IUPAC name
Trichloroacetic acid
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| Identifiers | |||
76-03-9  |
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| ChEMBL | ChEMBL14053 | ||
| Jmol 3D model | Interactive image | ||
| KEGG | C11150  |
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| PubChem | 6421 | ||
| RTECS number | AJ7875000 | ||
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| Properties | |||
| C2HCl3O2 | |||
| Molar mass | 163.38 g·mol−1 | ||
| Appearance | Colorless to white, crystalline solid | ||
| Odor | sharp, pungent [1] | ||
| Density | 1.63 g/cm3 | ||
| Melting point | 57 to 58 °C (135 to 136 °F; 330 to 331 K)[2] | ||
| Boiling point | 196 to 197 °C (385 to 387 °F; 469 to 470 K)[2] | ||
| Soluble in 0.1 parts[2] | |||
| Vapor pressure | 1 mmHg (51.1°C)[1] | ||
| Acidity (pKa) | 0.66[3] | ||
| Structure | |||
| 3.23 D | |||
| Vapor pressure | {{{value}}} | ||
| Related compounds | |||
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Related chloroacetic acids
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Chloroacetic acid Dichloroacetic acid |
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Related compounds
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Acetic acid Trifluoroacetic acid Tribromoacetic acid |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 verify (what is ?) |
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| Infobox references | |||
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as trichloroethanoic acid) is an analogue of acetic acid in which the three hydrogen atoms of the methyl group have all been replaced by chlorine atoms.
Synthesis
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
Use
It is widely used in biochemistry for the precipitation of macromolecules, such as proteins, DNA, and RNA. Solutions containing trichloroacetic acid as an ingredient are used for cosmetic treatments, such as chemical peels, 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.[4][5]
Salts and esters of trichloroacetic acid are called trichloroacetates.
Its sodium salt was used as an herbicide starting in the 1950s but regulators removed it from the market in the late 1980s and early 1990s.[6][7][8][9][10]
History
The discovery of trichloroacetic acid by Jean-Baptiste Dumas in 1839 delivered a striking example to the slowly evolving theory of organic radicals and valences.[11] The theory was contrary to the beliefs of Jöns Jakob Berzelius, starting a long dispute between Dumas and Berzelius.[12]
See also
References
- ↑ 1.0 1.1 NIOSH Pocket Guide to Chemical Hazards #0626National Institute for Occupational Safety and Health (NIOSH)
- ↑ 2.0 2.1 2.2 Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Databog fysik kemi, F&K Forlaget 11. udgave 2009
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ TCA-sodium in the Pesticide Properties DataBase (PPDB), accessed June 20, 2014
- ↑ G. S. Rai and C. L. Hamner Persistence of Sodium Trichloroacetate in Different Soil Types Weeds 2(4) Oct. 1953: 271-279
- ↑ OECD Trichloroacetic Acid CAS N°: 76-03-9 Accessed June 20, 2014
- ↑ EPA December 1991. trichloroacetic acid (TCA) EPA Cancellation 12/91 Accessed June 20, 2014
- ↑ PAN Trichloroacetic acid, sodium salt
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
