Orthoformic acid

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Orthoformic acid
Stereo skeletal formula of orthoformic acid
Identifiers
CAS number 463-78-5 YesY
PubChem 5231666
ChemSpider 4401409 YesY
Jmol-3D images Image 1
Properties
Molecular formula CH4O3
Molar mass 64.04 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

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

Orthoformic acid has not been isolated to date, and is believed to be unstable, decomposing into water and formic acid.[2]

Esters[edit]

Methanetriol esters, known as orthoformates, are well known and commercially available.[3][4] 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 are as mild dehydrating agent. Especially well known are trimethyl orthoformate, triethyl orthoformate, and triisopropyl orthoformate.

See also[edit]

References[edit]

  1. ^ "Methanetriol - PubChem". NCBI. Retrieved 22 April 2013. 
  2. ^ Böhm, S., Antipova, D. and Kuthan, J. (1996), "Study of methanetriol decomposition mechanisms". International Journal of Quantum Chemistry, volume 60, pages 649–655. doi:10.1002/(SICI)1097-461X(1996)60:2<649::AID-QUA3>3.0.CO;2-X
  3. ^ 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
  4. ^ H. W. Post (1943), "The Chemistry of the Aliphatic Orthoesters", Reinhold, 188 pages