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Orthoformic acid

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Orthoformic acid
Stereo skeletal formula of orthoformic acid Methanetriol.svg
Stereo skeletal formula of orthoformic acid
Names
Preferred IUPAC name
Methanetriol [1]
Other names
Orthoformic acid
Trihydroxymethane
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/CH4O3/c2-1(3)4/h1-4H Yes check.svgY
    Key: RLAHWVDQYNDAGG-UHFFFAOYSA-N Yes check.svgY
  • 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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Orthoformic acid or methanetriol is a chemical compound with the formula H C(OH)3. In this molecule, the central carbon atom is bound to one hydrogen and three hydroxyl groups.

Contents

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. [2] 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, [3] and also carbon dioxide and water. [4]

Esters

Methanetriol esters, known as orthoformates or ortho esters, are well known and commercially available. [5] [6] 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. ↑ Marks, Joshua H.; Bai, Xilin; Nikolayev, Anatoliy A.; Gong, Qi’ang; McAnally, Mason; Wang, Jia; Pan, Yang; Fortenberry, Ryan C.; Mebel, Alexander M.; Yang, Yao; Kaiser, Ralf I. (14 July 2025). "Methanetetrol and the final frontier in ortho acids". Nature Communications. doi:10.1038/s41467-025-61561-z.
  5. ↑ Sah, Peter P. T.; Ma, Tsu Sheng (July 1932). "ESTERS OF ORTHOFORMIC ACID". Journal of the American Chemical Society. 54 (7): 2964–2966. doi:10.1021/ja01346a048.
  6. ↑ H. W. Post (1943), "The Chemistry of the Aliphatic Orthoesters", Reinhold, 188 pages
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