Orthoformic acid

Orthoformic acid or methanetriol is a chemical compound with the formula HC(OH)3. In this molecule, the central carbon atom is bound to one hydrogen and three hydroxyl groups.

"Methanetriol" redirects here. Not to be confused with Methanethiol.
Orthoformic acid
Stereo skeletal formula of orthoformic acid
Names
Preferred IUPAC name
Methanetriol[1]
Other names
Orthoformic acid
Trihydroxymethane
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/CH4O3/c2-1(3)4/h1-4H checkY
    Key: RLAHWVDQYNDAGG-UHFFFAOYSA-N checkY
  • InChI=1/CH4O3/c2-1(3)4/h1-4H
    Key: RLAHWVDQYNDAGG-UHFFFAOYAS
  • OC(O)O
Properties
HC(OH)3
Molar mass 64.040 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Orthoformic acid was long held to be a hypothetical chemical compound too unstable to isolate or observe, as it was expected to decompose instantly into formic acid and water.[2] The compound was first observed in 2024 by mass spectrometry, which involved the electron-irradiated of a frozen mixture of methanol and oxygen.[3]

Esters

Methanetriol esters, known as orthoformates, are well known and commercially available.[4][5] 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.

See also

References
  1. "Methanetriol - PubChem". NCBI. Retrieved 22 April 2013.
  2. Bohm, Stanislav; Antipova, Diana; Kuthan, Josef (15 October 1996). "Study of methanetriol decomposition mechanisms". International Journal of Quantum Chemistry. 60 (2): 649–655. doi:10.1002/(SICI)1097-461X(1996)60:2<649::AID-QUA3>3.0.CO;2-X.
  3. >Marks, Joshua H.; Bai, Xilin; Nikolayev, Anatoliy A.; Gong, Qi’ang; Zhu, Cheng; Kleimeier, N. Fabian; Turner, Andrew M.; Singh, Santosh K.; Wang, Jia; Yang, Jiuzhong; Pan, Yang; Yang, Tao; Mebel, Alexander M.; Kaiser, Ralf I. (17 April 2024). "Methanetriol─Formation of an Impossible Molecule". Journal of the American Chemical Society. doi:10.1021/jacs.4c02637.
  4. Peter P. T. Sah, Tsu Sheng Ma (1932), ""ESTERS OF ORTHOFORMIC ACID". J. Am. Chem. Soc., volume 54, issue 7, pages 2964–2966 doi:10.1021/ja01346a048
  5. H. W. Post (1943), "The Chemistry of the Aliphatic Orthoesters", Reinhold, 188 pages
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