Orthoformic acid or methanetriol is a

hypothetical chemical compound A hypothetical chemical compound is a chemical compound that has been conceived of, but is not known to have been synthesized, observed, or isolated (identified or shown to exist). Some hypothetical compounds cannot form at all. Others might tur ...

with the formula . In this molecule, the central carbon atom is bound to one

hydrogen Hydrogen is the chemical element with the symbol H and atomic number 1. Hydrogen is the lightest element. At standard conditions hydrogen is a gas of diatomic molecules having the formula . It is colorless, odorless, tasteless, non-toxic, an ...

and three

hydroxyl In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy ...

groups. Orthoformic acid has not been isolated to date, and is believed to be unstable, decomposing into

water Water (chemical formula ) is an inorganic, transparent, tasteless, odorless, and nearly colorless chemical substance, which is the main constituent of Earth's hydrosphere and the fluids of all known living organisms (in which it acts as a ...

and

formic acid Formic acid (), systematically named methanoic acid, is the simplest carboxylic acid, and has the chemical formula HCOOH and structure . It is an important intermediate in chemical synthesis and occurs naturally, most notably in some ants. Es ...

.Böhm, S., Antipova, D. and Kuthan, J. (1996), "Study of methanetriol decomposition mechanisms". ''International Journal of Quantum Chemistry'', volume 60, pages 649–655.

Esters

Methanetriol

ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ar ...

s, known as orthoformates, are well known and commercially available.Peter P. T. Sah, Tsu Sheng Ma (1932), ""ESTERS OF ORTHOFORMIC ACID". ''J. Am. Chem. Soc.'', volume 54, issue 7, pages 2964–2966 H. W. Post (1943), "The Chemistry of the Aliphatic Orthoesters", Reinhold, 188 pages Like

acetal In organic chemistry, an acetal is a functional group with the connectivity . Here, the R groups can be organic fragments (a carbon atom, with arbitrary other atoms attached to that) or hydrogen, while the R' groups must be organic fragments no ...

s, 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 Trimethyl orthoformate (TMOF) is the organic compound with the formula HC(OCH3)3. A colorless liquid, it is the simplest orthoester. It is a reagent used in organic synthesis for the formation of methyl ethers. The product of reaction of an ald ...

triethyl orthoformate Triethyl orthoformate is an organic compound with the formula HC(OC2H5)3. This colorless volatile liquid, the orthoester of formic acid, is commercially available. The industrial synthesis is from hydrogen cyanide and ethanol. It may also be pr ...

, and triisopropyl orthoformate.

References

{{DEFAULTSORT:Orthoformic Acid Organic acids Dehydrating agents Hypothetical chemical compounds

Esters

See also

References