Trichloroacetic acid
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{{Chembox new
| Name = Trichloroacetic acid
| ImageFileL1 = Trichloroacetic-acid-2D-skeletal.png
| ImageSizeL1 =100px
| ImageFileR1 = Trichloroacetic-acid-3D-vdW.png
| ImageSizeR1 =120px
| ImageFile2 = Trichloroacetic-acid-elpot.png
| ImageSize2 =150px
| IUPACName = Trichloroacetic acid
| Section1 = {{Chembox Identifiers
| SMILES = ClC(Cl)(Cl)C(O)=O
| CASNo = 76-03-9
| RTECS = AJ7875000
}}
| Section2 = {{Chembox Properties
| Formula = CCl<sub>3</sub>COOH
| MolarMass = 163.4 g/mol
| Appearance = white solid
| Density = 1.63 g/cm³, solid
| Solubility = very good
| MeltingPt = 57 °C
| BoilingPt = 196 °C
| pKa = 0.77<ref>[http://www.cem.msu.edu/~reusch/VirtTxtJml/acidity2.htm Ionization Constants of Heteroatom Organic Acids]</ref>
}}
| Section3 = {{Chembox Structure
| Dipole = 3.23 [[Debye|D]]
}}
| Section7 = {{Chembox Hazards
| ExternalMSDS =
| EUClass = Corrosive '''C''')<br />Dangerous for<br />the environment ('''N''')
| RPhrases = {{R35}}, {{R50/53}}
| SPhrases = {{S1/2}}, {{S26}}, {{S36/37/39}},<br />{{S45}}, {{S60}}, {{S61}}
| FlashPt =
}}
| Section8 = {{Chembox Related
| Function = [[chloroacetic acids]]
| OtherFunctn = [[Chloroacetic acid]]<br />[[Dichloroacetic acid]]
| OtherCpds = [[Acetic acid]]<br />[[Trifluoroacetic acid]]<br />[[Tribromoacetic acid]]
}}
}}
'''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acid''') is an analogue of [[acetic acid]] in which the three [[hydrogen]] atoms of the [[methyl]] group have all been replaced by [[chlorine]] atoms.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]].
:CH<sub>3</sub>COOH + 3Cl<sub>2</sub> → CCl<sub>3</sub>COOH + 3HCl
It is widely used in [[biochemistry]] for the precipitation of macromolecules such as [[protein]]s, [[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 [[wart]]s, including [[genital wart]]s. It can kill normal cells as well. It is considered safe for use for this purpose during pregnancy<ref>[http://www.webmd.com/sexual-conditions/hpv-genital-warts/trichloroacetic-acid-or-bichloroacetic-acid-for-genital-warts-human-papillomavirus Wiley DJ, et al. (2002). External genital warts: Diagnosis, treatment, and prevention. Clinical Infectious Diseases, 35(Suppl 2): S210–S224]</ref>.
[[Salt]]s 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]]<ref>[http://potency.lbl.gov/chempages/TRICHLOROACETIC%20ACID.html The Carcinogenic Potency Database (CPDB)]</ref>.
==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.<ref>{{cite journal
| author = Dumas
| year = 1840
| title = Trichloroacetic acid
| journal = [[Annalen der Chemie]]
| volume = XXXII
| pages = 101
}}</ref> The theory was contrary to the beliefs of [[Jöns Jakob Berzelius]], starting a long dispute between Dumas and Berzelius.<ref>{{cite journal
| author = William Albert Noyes
| year = 1927
| title = Valence
| journal = [[Proceedings of the American Philosophical Society]]
| volume = 66
| pages = 287–308
| url = http://links.jstor.org/sici?sici=0003-049X%281927%2966%3C287%3AV%3E2.0.CO%3B2-K
}}</ref>
==See also==
*[[Chloroacetic acids]]
==References==
<div class="references-small"><references/></div>
==External links==
*{{ICSC|0586|05}}
[[Category:Carboxylic acids]]
[[Category:Organochlorides]]
[[de:Trichloressigsäure]]
[[es:Ácido tricloroacético]]
[[fr:Acide trichloroacétique]]
[[id:Asam trikloroasetat]]
[[it:Acido tricloroacetico]]
[[hu:Triklórecetsav]]
[[nl:Trichloorazijnzuur]]
[[ja:トリクロロ酢酸]]
[[pl:Kwas trichlorooctowy]]
[[pt:Ácido tricloroacético]]
[[ru:Трихлоруксусная кислота]]
[[sv:Triklorättiksyra]]
[[zh:三氯乙酸]]