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Orthoformic acid

Hypothetical molecule with the formula HC(OH)3

Summary

Hypothetical molecule with the formula HC(OH)3

Trihydroxymethane

Orthoformic acid or methanetriol is a chemical compound with the formula . In this molecule, the central carbon atom is bound to one hydrogen and three hydroxyl groups.

Orthoformic acid was long held to be a hypothetical chemical compound, as it was expected to decompose instantly into formic acid and water, making it too unstable to isolate or observe. However, observation was shown to be possible in 2024, when it was identified by mass spectrometry. This involved the electron-irradiation of a frozen mixture of methanol and oxygen, and also carbon dioxide and water.

Esters

Main article: Ortho ester

Methanetriol esters, known as orthoformates or ortho esters, are well known and commercially available. Like acetals, they are stable towards bases but easily hydrolyzed in acidic conditions to the alcohol and an ester of formic acid. They are used as mild dehydrating agents. Especially well known are trimethyl orthoformate, triethyl orthoformate, and triisopropyl orthoformate.

References

References

  1. "Methanetriol - PubChem". NCBI.
  2. (15 October 1996). "Study of methanetriol decomposition mechanisms". International Journal of Quantum Chemistry.
  3. (17 April 2024). "Methanetriol─Formation of an Impossible Molecule". Journal of the American Chemical Society.
  4. (14 July 2025). "Methanetetrol and the final frontier in ortho acids". Nature Communications.
  5. (July 1932). "ESTERS OF ORTHOFORMIC ACID". Journal of the American Chemical Society.
  6. H. W. Post (1943), "The Chemistry of the Aliphatic Orthoesters", Reinhold, 188 pages
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.

organic-acids dehydrating-agents
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