orthoformic acid
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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.


See also

*
Methanol Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical and the simplest aliphatic alcohol, with the formula C H3 O H (a methyl group linked to a hydroxyl group, often abbreviated as MeOH). It is a ...
*
Methanediol Methanediol, also known as formaldehyde monohydrate or methylene glycol, is an organic compound with chemical formula . It is the simplest geminal diol, and the simplest sugar alcohol. In aqueous solutions it coexists with oligomers (short polym ...
* Orthoacetic acid *
Orthocarbonic acid Orthocarbonic acid (methanetetrol) is the name given to a hypothetical compound with the chemical formula or . Its molecular structure consists of a single carbon atom bonded to four hydroxy groups. It would be therefore a fourfold alcohol. ...
(methanetetrol)


References

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