Orthoformic acid

Orthoformic acid
Names
	Preferred IUPAC name Methanetriol
	Other names Orthoformic acid; Trihydroxymethane
Identifiers
CAS Number	463-78-5 ;
3D model (JSmol)	Interactive image;
ChemSpider	4401409 ;
PubChem CID	5231666;
UNII	WIU6G972U6 ;
CompTox Dashboard (EPA)	DTXSID50894118 ;
	InChI InChI=1S/CH4O3/c2-1(3)4/h1-4H Key: RLAHWVDQYNDAGG-UHFFFAOYSA-N ; InChI=1/CH4O3/c2-1(3)4/h1-4H Key: RLAHWVDQYNDAGG-UHFFFAOYAS;
	SMILES OC(O)O;
Properties
Chemical formula	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). verify (what is ?) Infobox references

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.

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]

Esters

Methanetriol esters, known as orthoformates or ortho esters, 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.

References

^ "Methanetriol - PubChem". NCBI. Retrieved 22 April 2013.
^ 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.
^ >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.
^ 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.
^ H. W. Post (1943), "The Chemistry of the Aliphatic Orthoesters", Reinhold, 188 pages

[pubchem.ncbi.nlm.nih.gov-1] "Methanetriol - PubChem". NCBI. Retrieved 22 April 2013.

[Bohm-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.

[Marks-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.

[Sah37-4] 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.

[Post43-5] H. W. Post (1943), "The Chemistry of the Aliphatic Orthoesters", Reinhold, 188 pages

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[2]

[3]

[4]

[5]

Esters

See also

References