Trichloroacetic acid 1111806 224721150 2008-07-10T03:13:35Z Puppy8800 5404759 iw {{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acid''') is an analogue of [[acetic acid]] in which the three [[hydrogen]] atoms of the [[methyl]] group have all been replaced by [[chlorine]] atoms.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]]