Surf Wiki
Save to docs
general/acetic-acids

From Surf Wiki (app.surf) — the open knowledge base

Trichloroacetic acid

| NFPA-F = 1 | NFPA-H = 3 | NFPA-R = 0 | NFPA-S = Dichloroacetic acid Trifluoroacetic acid Tribromoacetic acid

Trichloroacetic acid (TCA; TCAA; 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as trichloroethanoic acid) is an analogue of acetic acid in which the three hydrogen atoms of the methyl group have all been replaced by chlorine atoms. Salts and esters of trichloroacetic acid are called trichloroacetates.

Synthesis

Trichloroacetic acid was discovered by Jean-Baptiste Dumas in 1830.

It is prepared by the reaction of chlorine with acetic acid in the presence of a suitable catalyst such as red phosphorus. This reaction is Hell–Volhard–Zelinsky halogenation. : + 3 → + 3 Another route to trichloroacetic acid is the oxidation of trichloroacetaldehyde.

Use

Trichloroacetic acid is widely used in biochemistry for the precipitation of macromolecules, such as proteins, DNA, and RNA. TCA is used during oligonucleotide synthesis during the "deblocking" step to remove the dimethoxytrityl protecting group from the growing DNA/RNA strand for the next nucleotide incorporation. TCA and DCA are both used in cosmetic treatments (such as chemical peels and tattoo removal) and as topical medication for chemoablation of warts, including genital warts. It can kill normal cells as well. It is considered safe for use for this purpose during pregnancy.

The sodium salt (sodium trichloroacetate) was used as an herbicide starting in the 1950s but regulators removed it from the market in the late 1980s and early 1990s.

Environmental and health concerns

According to the European Chemicals Agency, "This substance causes severe skin burns and eye damage, is very toxic to aquatic life and has long lasting toxic effects."

History

The discovery of trichloroacetic acid by Jean-Baptiste Dumas in 1839 delivered a striking example to the slowly evolving theory of organic radicals and valences.{{cite journal

References

References

  1. [https://www.cdc.gov/niosh/npg/npgd0626.html NIOSH Pocket Guide to Chemical Hazards #0626] [[National Institute for Occupational Safety and Health]] (NIOSH)
  2. {{Merck12th
  3. Databog fysik kemi, F&K Forlaget 11. udgave 2009
  4. ''Terchloracetic Acid'' in Gmelin, L., Hand-book of Chemistry: Organic chemistry
  5. Jones, Kirtly. (June 21, 2012). "Trichloroacetic Acid or Bichloroacetic Acid for Genital Warts (Human Papillomavirus)". HealthWise.
  6. (2002). "External genital warts: Diagnosis, treatment, and prevention". Clinical Infectious Diseases.
  7. {{PPDB. 609
  8. G. S. Rai and C. L. Hamner. "Persistence of Sodium Trichloroacetate in Different Soil Types." ''Weeds'' 2(4) Oct. 1953: 271-279. [[JSTOR]] [https://www.jstor.org/stable/4040104 4040104]. [[Digital Object Identifier. DOI]] 10.2307/4040104.
  9. United Nations Environment Programme. "[https://web.archive.org/web/20180815164222/http://www.inchem.org/documents/sids/sids/76039.pdf Trichloroacetic Acid CAS N°: 76-03-9]" ([[OECD SIDS]]). Accessed June 20, 2014. Archived from [http://www.inchem.org/documents/sids/sids/76039.pdf the original] on 15 August 2018.
  10. Heier, Al (December 1991). "[https://web.archive.org/web/20200815134410/https://pmep.cce.cornell.edu/profiles/herb-growthreg/sethoxydim-vernolate/tca/tca-12-91-rer.html Trichloroacetic Acid (TCA)]". EPA. Accessed June 20, 2014 — via [[Cornell]] PMEP Pesticide Active Ingredient Information database. Archived from [https://pmep.cce.cornell.edu/profiles/herb-growthreg/sethoxydim-vernolate/tca/tca-12-91-rer.html the original] on 15 Aug 2020.
  11. "Trichloroacetic acid". [[European Chemical Agency]].
Info: Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

acetic-acids iarc-group-2b-carcinogens trichloromethyl-compounds organic-compounds-with-2-carbon-atoms recreational-drug-metabolites
Want to explore this topic further?

Ask Mako anything about Trichloroacetic acid — get instant answers, deeper analysis, and related topics.

Research with Mako

Free with your Surf account

Content sourced from Wikipedia, available under CC BY-SA 4.0.

This content may have been generated or modified by AI. CloudSurf Software LLC is not responsible for the accuracy, completeness, or reliability of AI-generated content. Always verify important information from primary sources.

Report