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Trichloroacetic acid

 
Sci-Tech Dictionary: trichloroacetic acid
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(trī¦klör·ō·ə¦sed·ik ′as·əd)

(organic chemistry) CCl3COOH Toxic, deliquescent, colorless crystals with a pungent aroma; soluble in water, alcohol, and ether; boils at 198°C; used as a chemical intermediate and laboratory reagent, and in medicine, pharmacy, and herbicides. Abbreviated TCA.

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Wikipedia: Trichloroacetic acid
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Trichloroacetic acid
IUPAC name
Identifiers
CAS number 76-03-9
RTECS number AJ7875000
SMILES
Properties
Molecular formula C2HCl3O2
Molar mass 163.4 g/mol
Appearance white solid
Density 1.63 g/cm³, solid
Melting point

57 °C
Boiling point

196 °C
Solubility in water very good
Solubility in methanol methanol 9.91 M [1]
Acidity (pKa) 0.77[2]
Structure
Dipole moment 3.23 D
Hazards
EU classification Corrosive C)
Dangerous for
the environment (N)
R-phrases R35, R50/53
S-phrases (S1/2), S26, S36/37/39,
S45, S60, S61
Related compounds
Related chloroacetic acids Chloroacetic acid
Dichloroacetic acid
Related compounds Acetic acid
Trifluoroacetic acid
Tribromoacetic acid
 Y(what is this?)  (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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as trichloroethanoic acid) is an analogue of acetic acid in which the three hydrogen atoms of the methyl group have all been replaced by chlorine atoms.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 cosmetic treatments such as chemical peels and 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[3].

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[4].

Contents

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.[5] The theory was contrary to the beliefs of Jöns Jakob Berzelius, starting a long dispute between Dumas and Berzelius.[6]

See also

References

  1. ^ Solubility of trichloroacetic acid in methanol
  2. ^ Ionization Constants of Heteroatom Organic Acids
  3. ^ Wiley DJ, et al. (2002). External genital warts: Diagnosis, treatment, and prevention. Clinical Infectious Diseases, 35(Suppl 2): S210–S224
  4. ^ The Carcinogenic Potency Database (CPDB)
  5. ^ Dumas (1840). "Trichloroacetic acid". Annalen der Chemie XXXII: 101. 
  6. ^ William Albert Noyes (1927). "Valence". Proceedings of the American Philosophical Society 66: 287–308. http://links.jstor.org/sici?sici=0003-049X%281927%2966%3C287%3AV%3E2.0.CO%3B2-K. 

External links


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