Trichloroacetic acid Information & Trichloroacetic acid Links at HealthHaven.com

Trichloroacetic acid
IUPAC name	Trichloroacetic acid
Identifiers
CAS number	76-03-9
RTECS number	AJ7875000
SMILES	ClC(Cl)(Cl)C(O)=O
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
Acidity (pKa)	0.77
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
	(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as trichloroethanoic acid) is an analogue of acetic acid in which the three hydrogen atoms of the methyl group have all been replaced by chlorine atoms.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].

[edit] 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]

[edit] See also

Chloroacetic acids

[edit] References

^ Solubility of trichloroacetic acid in methanol
^ Ionization Constants of Heteroatom Organic Acids
^ Wiley DJ, et al. (2002). External genital warts: Diagnosis, treatment, and prevention. Clinical Infectious Diseases, 35(Suppl 2): S210–S224
^ The Carcinogenic Potency Database (CPDB)
^ Dumas (1840). "Trichloroacetic acid". Annalen der Chemie XXXII: 101.
^ 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.

[edit] External links

International Chemical Safety Card 0586

[0] Solubility of trichloroacetic acid in methanol

[1] Ionization Constants of Heteroatom Organic Acids

[2] Wiley DJ, et al. (2002). External genital warts: Diagnosis, treatment, and prevention. Clinical Infectious Diseases, 35(Suppl 2): S210–S224

[3] The Carcinogenic Potency Database (CPDB)

[4] Dumas (1840). "Trichloroacetic acid". Annalen der Chemie XXXII: 101.

[5] 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.

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Contents

[edit] History

[edit] See also

[edit] References

[edit] External links