Orthoformic acid

Last updated
Orthoformic acid
Methanetriol.svg
Names
Preferred IUPAC name
Methanetriol [1]
Other names
Orthoformic acid
Trihydroxymethane
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/CH4O3/c2-1(3)4/h1-4H Yes check.svgY
    Key: RLAHWVDQYNDAGG-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/CH4O3/c2-1(3)4/h1-4H
    Key: RLAHWVDQYNDAGG-UHFFFAOYAS
  • OC(O)O
Properties
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).
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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.

Contents

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.

See also

Related Research Articles

<span class="mw-page-title-main">Ester</span> Compound derived from an acid

In chemistry, an ester is a compound derived from an acid in which the hydrogen atom (H) of at least one acidic hydroxyl group of that acid is replaced by an organyl group. Analogues derived from oxygen replaced by other chalcogens belong to the ester category as well. According to some authors, organyl derivatives of acidic hydrogen of other acids are esters as well, but not according to the IUPAC.

<span class="mw-page-title-main">Formic acid</span> Simplest carboxylic acid (HCOOH)

Formic acid, systematically named methanoic acid, is the simplest carboxylic acid, and has the chemical formula HCOOH and structure H−C(=O)−O−H. It is an important intermediate in chemical synthesis and occurs naturally, most notably in some ants. Esters, salts and the anion derived from formic acid are called formates. Industrially, formic acid is produced from methanol.

<span class="mw-page-title-main">Dinitrogen pentoxide</span> Chemical compound

Dinitrogen pentoxide is the chemical compound with the formula N2O5. It is one of the binary nitrogen oxides, a family of compounds that only contain nitrogen and oxygen. It exists as colourless crystals that sublime slightly above room temperature, yielding a colorless gas.

<span class="mw-page-title-main">Formate</span> Salt or ester of formic acid

Formate is the conjugate base of formic acid. Formate is an anion or its derivatives such as ester of formic acid. The salts and esters are generally colorless.

<span class="mw-page-title-main">Organic peroxides</span> Organic compounds of the form R–O–O–R’

In organic chemistry, organic peroxides are organic compounds containing the peroxide functional group. If the R′ is hydrogen, the compounds are called hydroperoxides, which are discussed in that article. The O−O bond of peroxides easily breaks, producing free radicals of the form RO. Thus, organic peroxides are useful as initiators for some types of polymerization, such as the acrylic, unsaturated polyester, and vinyl ester resins used in glass-reinforced plastics. MEKP and benzoyl peroxide are commonly used for this purpose. However, the same property also means that organic peroxides can explosively combust. Organic peroxides, like their inorganic counterparts, are often powerful bleaching agents.

<span class="mw-page-title-main">Meldrum's acid</span> Chemical compound

Meldrum's acid or 2,2-dimethyl-1,3-dioxane-4,6-dione is an organic compound with formula C6H8O4. Its molecule has a heterocyclic core with four carbon and two oxygen atoms; the formula can also be written as [−O−(C 2)−O−(C=O)−(CH2)−(C=O)−].

<span class="mw-page-title-main">Polyyne</span> Any organic compound with alternating C–C and C≡C bonds

A polyyne is any organic compound with alternating single and triple bonds; that is, a series of consecutive alkynes, (−C≡C−)n with n greater than 1. These compounds are also called polyacetylenes, especially in the natural products and chemical ecology literature, even though this nomenclature more properly refers to acetylene polymers composed of alternating single and double bonds (−CR=CR′−)n with n greater than 1. They are also sometimes referred to as oligoynes, or carbinoids after "carbyne" (−C≡C−), the hypothetical allotrope of carbon that would be the ultimate member of the series. The synthesis of this substance has been claimed several times since the 1960s, but those reports have been disputed. Indeed, the substances identified as short chains of "carbyne" in many early organic synthesis attempts would be called polyynes today.

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<span class="mw-page-title-main">Ortho ester</span> Chemical group with the structure RC(OR)3

In organic chemistry, an ortho ester is a functional group containing three alkoxy groups attached to one carbon atom, i.e. with the general formula RC(OR′)3. Orthoesters may be considered as products of exhaustive alkylation of unstable orthocarboxylic acids and it is from these that the name 'ortho ester' is derived. An example is ethyl orthoacetate, CH3C(OCH2CH3)3, more correctly known as 1,1,1-triethoxyethane.

<span class="mw-page-title-main">Triethyl orthoformate</span> Chemical compound

Triethyl orthoformate is an organic compound with the formula HC(OC2H5)3. This colorless volatile liquid, the ortho ester of formic acid, is commercially available. The industrial synthesis is from hydrogen cyanide and ethanol.

<span class="mw-page-title-main">Sodium methoxide</span> Ionic organic compound (CH3ONa)

Sodium methoxide is the simplest sodium alkoxide. With the formula CH3ONa, it is a white solid, which is formed by the deprotonation of methanol. It is a widely used reagent in industry and the laboratory. It is also a dangerously caustic base.

<span class="mw-page-title-main">Boronic acid</span> Organic compound of the form R–B(OH)2

A boronic acid is an organic compound related to boric acid in which one of the three hydroxyl groups is replaced by an alkyl or aryl group. As a compound containing a carbon–boron bond, members of this class thus belong to the larger class of organoboranes.

<span class="mw-page-title-main">Sulfenic acid</span> Organosulfur compound of the form R–SOH

In chemistry, a sulfenic acid is an organosulfur compound and oxoacid with the general formula R−S−OH. It is the first member of the family of organosulfur oxoacids, which also include sulfinic acids and sulfonic acids, respectively. The base member of the sulfenic acid series with R = H is hydrogen thioperoxide.

Selenoxide elimination is a method for the chemical synthesis of alkenes from selenoxides. It is most commonly used to synthesize α,β-unsaturated carbonyl compounds from the corresponding saturated analogues. It is mechanistically related to the Cope reaction.

<span class="mw-page-title-main">Achmatowicz reaction</span> Organic synthesis

The Achmatowicz reaction, also known as the Achmatowicz rearrangement, is an organic synthesis in which a furan is converted to a dihydropyran. In the original publication by the Polish Chemist Osman Achmatowicz Jr. in 1971 furfuryl alcohol is reacted with bromine in methanol to 2,5-dimethoxy-2,5-dihydrofuran which rearranges to the dihydropyran with dilute sulfuric acid. Additional reaction steps, alcohol protection with methyl orthoformate and boron trifluoride) and then ketone reduction with sodium borohydride produce an intermediate from which many monosaccharides can be synthesised.

<span class="mw-page-title-main">Acetic acid</span> Colorless and faint organic acid found in vinegar

Acetic acid, systematically named ethanoic acid, is an acidic, colourless liquid and organic compound with the chemical formula CH3COOH. Vinegar is at least 4% acetic acid by volume, making acetic acid the main component of vinegar apart from water. It has been used, as a component of vinegar, throughout history from at least the third century BC.

<span class="mw-page-title-main">Methyl chloroformate</span> Chemical compound

Methyl chloroformate is a chemical compound with the chemical formula Cl−C(=O)−O−CH3. It is the methyl ester of chloroformic acid. It is an oily colorless liquid, although aged samples appear yellow. It is also known for its pungent odor.

<span class="mw-page-title-main">Trimethyl orthoformate</span> Chemical compound

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 aldehyde with trimethyl orthoformate is an acetal. In general cases, these acetals can be deprotected back to the aldehyde by using hydrochloric acid.

<span class="mw-page-title-main">Nitrate ester</span> Chemical group (–ONO2)

In organic chemistry, a nitrate ester is an organic functional group with the formula R−ONO2, where R stands for any organyl group. They are the esters of nitric acid and alcohols. A well-known example is nitroglycerin, which is not a nitro compound, despite its name.

<span class="mw-page-title-main">Borinic acid</span> Chemical compound

Borinic acid, also known as boronous acid, is an oxyacid of boron with formula H
2
BOH
. Borinate is the associated anion of borinic acid with formula H
2
BO
; however, being a Lewis acid, the form in basic solution is H
2
B(OH)
2
.

References

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