Orthoformic acid

Orthoformic acid
IUPAC name

Orthoformic acid
Systematic name

Methanetriol[1]
Other names

Trihydroxymethane
Identifiers
CAS number 463-78-5 N
PubChem 5231666
ChemSpider 4401409 Y
Jmol-3D images Image 1
Properties
Molecular formula CH4O3
Molar mass 64.04 g mol−1
Exact mass 64.016043994 g mol-1
 Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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.

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

Esters

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

References

  1. ^ http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=5231666&loc=ec_rcs
  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