Trichloroacetic acid

Trichloroacetic acid

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 = CCl3COOH
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 [ [http://www.cem.msu.edu/~reusch/VirtTxtJml/acidity2.htm Ionization Constants of Heteroatom Organic Acids] ]
Section3 = Chembox Structure
Dipole = 3.23 D
Section7 = Chembox Hazards
ExternalMSDS =
EUClass = Corrosive C)
Dangerous for
the environment (N)
RPhrases = R35, R50/53
SPhrases = S1/2, S26, S36/37/39,
S45, S60, S61
FlashPt =
Section8 = Chembox Related
Function = chloroacetic acids
OtherFunctn = Chloroacetic acid
Dichloroacetic acid
OtherCpds = Acetic acid
Trifluoroacetic acid
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as trichloroethanoic acid) is an analogue of acetic acid in which the three hydrogen atoms of the methyl group have all been replaced by chlorine atoms.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.: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 [ [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] ] .

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 [ [http://potency.lbl.gov/chempages/TRICHLOROACETIC%20ACID.html The Carcinogenic Potency Database (CPDB)] ] .

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. [cite journal
author = Dumas
year = 1840
title = Trichloroacetic acid
journal = Annalen der Chemie
volume = XXXII
pages = 101 ] The theory was contrary to the beliefs of Jöns Jakob Berzelius, starting a long dispute between Dumas and Berzelius. [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 ]

ee also

*Chloroacetic acids

References

External links

*ICSC|0586|05


Wikimedia Foundation. 2010.

Игры ⚽ Поможем написать реферат

Look at other dictionaries:

  • trichloroacetic acid — [trī klôr΄ō ə sēt′ik] n. [ TRI + CHLORO + ACETIC] a colorless, corrosive, deliquescent, crystalline substance, CCl3COOH, with a sharp, pungent odor: it is used as an antiseptic and astringent …   English World dictionary

  • trichloroacetic acid — trichloracto rūgštis statusas T sritis chemija formulė CCl₃COOH atitikmenys: angl. trichloroacetic acid rus. трихлоруксусная кислота ryšiai: sinonimas – trichloretano rūgštis …   Chemijos terminų aiškinamasis žodynas

  • trichloroacetic acid — Used as an astringent antiseptic in 1–5% solution or as an escharotic for venereal and other warts; a widely used protein precipitant. * * * tri·chlo·ro·ace·tic acid .trī .klōr ō ə .sēt ik , .klȯr also tri·chlor·ace·tic acid .klōr ə .sēt ik n a… …   Medical dictionary

  • trichloroacetic acid — noun a strong acid made by chlorinating acetic acid (Freq. 1) • Syn: ↑trichloracetic acid • Hypernyms: ↑acetic acid, ↑ethanoic acid …   Useful english dictionary

  • trichloroacetic acid — also trichloracetic acid noun Etymology: International Scientific Vocabulary Date: 1885 a strong vesicant pungent acid C2Cl3HO2 used in weed control and in medicine as a caustic and astringent …   New Collegiate Dictionary

  • trichloroacetic acid — /truy klawr oh euh see tik, set ik, klohr , klawr , klohr /, Chem. a toxic, deliquescent, and colorless crystalline compound, C2HCl3O2, soluble in water, alcohol, and ether: used in the synthesis of pharmaceuticals, herbicides, and other… …   Universalium

  • trichloroacetic acid — noun The chlorinated derivative of acetic acid CCl COOH used as a herbicide and topical antiseptic …   Wiktionary

  • trichloroacetic acid — /traɪˌklɔroʊəˌsitɪk ˈæsəd/ (say truy.klawrohuh.seetik asuhd) noun a strong poisonous acid, CCl3COOH; used in medicine and pharmacy, and as a herbicide …  

  • trichloroacetic acid — tri•chlo′ro•a•ce′tic ac′id [[t]traɪˈklɔr oʊ əˈsi tɪk, ˈsɛt ɪk, ˈkloʊr , ˌklɔr , ˌkloʊr [/t]] n. chem. a toxic compound, C2HCl3O2, used in the synthesis of pharmaceuticals, herbicides, and other chemicals, and as a reagent for the detection of… …   From formal English to slang

  • trichloroacetic — adjective Of or pertaining to trichloroacetic acid or its derivatives …   Wiktionary

Share the article and excerpts

Direct link
… Do a right-click on the link above
and select “Copy Link”