Orthoformic Acid
   HOME
*





Orthoformic Acid
Orthoformic acid or methanetriol is a hypothetical chemical compound with the formula . In this molecule, the central carbon atom 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.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 esters, 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 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 ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


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 turn out to be highly unstable, decomposing, isomerizing, polymerizing, rearranging, or disproportionating. Some are thought to exist only briefly as reactive intermediates, or in vacuum (e.g. helium hydride ion). Some cannot hold together due to steric hindrance (e.g. tetra-''tert''-butylmethane) or bond stress (e.g. tetrahedrane). Some have no known pathway for synthesis (e.g. hypercubane). Some compounds of radioactive elements have never been synthesized due to their radioactive decay and short half-lives (e.g. francium hydroxide) Some "parent compounds" have not been or cannot be isolated, even though stable structural analogs with substituents have been discovered or synthesized (e.g. borole). Hypothetical compounds are often p ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


picture info

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, and highly combustible. Hydrogen is the most abundant chemical substance in the universe, constituting roughly 75% of all normal matter.However, most of the universe's mass is not in the form of baryons or chemical elements. See dark matter and dark energy. Stars such as the Sun are mainly composed of hydrogen in the plasma state. Most of the hydrogen on Earth exists in molecular forms such as water and organic compounds. For the most common isotope of hydrogen (symbol 1H) each atom has one proton, one electron, and no neutrons. In the early universe, the formation of protons, the nuclei of hydrogen, occurred during the first second after the Big Bang. The emergence of neutral hydrogen atoms throughout the universe occurred about 370,000 ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


picture info

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. Both the negatively charged anion , called hydroxide, and the neutral radical , known as the hydroxyl radical, consist of an unbonded hydroxy group. According to IUPAC definitions, the term ''hydroxyl'' refers to the hydroxyl radical () only, while the functional group is called a ''hydroxy group''. Properties Water, alcohols, carboxylic acids, and many other hydroxy-containing compounds can be readily deprotonated due to a large difference between the electronegativity of oxygen (3.5) and that of hydrogen (2.1). Hydroxy-containing compounds engage in intermolecular hydrogen bonding increasing the electrostatic attraction between molecules and thus to higher boiling and melting points than found for compounds that lack this f ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


picture info

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 solvent). It is vital for all known forms of life, despite not providing food, energy or organic micronutrients. Its chemical formula, H2O, indicates that each of its molecules contains one oxygen and two hydrogen atoms, connected by covalent bonds. The hydrogen atoms are attached to the oxygen atom at an angle of 104.45°. "Water" is also the name of the liquid state of H2O at standard temperature and pressure. A number of natural states of water exist. It forms precipitation in the form of rain and aerosols in the form of fog. Clouds consist of suspended droplets of water and ice, its solid state. When finely divided, crystalline ice may precipitate in the form of snow. The gaseous state of water is steam or water vapor. Water co ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


picture info

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. Esters, salts and the anion derived from formic acid are called formates. Industrially, formic acid is produced from methanol. Natural occurrence In nature, formic acid is found in most ants and in stingless bees of the genus ''Oxytrigona''. Wood ants from the genus ''Formica'' can spray formic acid on their prey or to defend the nest. The puss moth caterpillar (''Cerura vinula'') will spray it as well when threatened by predators. It is also found in the trichomes of stinging nettle (''Urtica dioica''). Apart from that, this acid is incorporated in many fruits such as pineapple (0.21mg per 100g), apple (2mg per 100g) and kiwi (1mg per 100g), as well as in many vegetables, namely onion (45mg per 100g), eggplant (1.34 mg per 100g) and, in ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


picture info

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 are fatty acid esters of glycerol; they are important in biology, being one of the main classes of lipids and comprising the bulk of animal fats and vegetable oils. Esters typically have a pleasant smell; those of low molecular weight are commonly used as fragrances and are found in essential oils and pheromones. They perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Polyesters are important plastics, with monomers linked by ester moieties. Phosphoesters form the backbone of DNA molecules. Nitrate esters, such as nitroglycerin, are known for their explosive properties. '' Nomenclature Etymology Th ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


picture info

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 not hydrogen. The two R' groups can be equivalent to each other (a "symmetric acetal") or not (a "mixed acetal"). Acetals are formed from and convertible to aldehydes or ketones and have the same oxidation state at the central carbon, but have substantially different chemical stability and reactivity as compared to the analogous carbonyl compounds. The central carbon atom has four bonds to it, and is therefore saturated and has tetrahedral geometry. The term ketal is sometimes used to identify structures associated with ketones (both R groups organic fragments rather than hydrogen) rather than aldehydes and, historically, the term acetal was used specifically for the aldehyde-related cases (having at least one hydrogen in place of an ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


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 aldehyde with trimethyl orthoformate is an acetal. In general cases, these acetals can be deprotected back to the aldehyde by using hydrochloric acid. Synthesis Trimethyl orthoformate is prepared on an industrial scale by the methanolysis of hydrogen cyanide:Ashford's Dictionary of Industrial Chemicals, Third edition, 2011, , page 9388 :HCN + 3 HOCH3 → HC(OCH3)3 + NH3 Trimethyl orthoformate can also be prepared from the reaction between chloroform and sodium methoxide, an example of the Williamson ether synthesis. Use Trimethyl orthoformate is a useful building block for creating methoxymethylene groups and heterocyclic ring systems. It introduces a formyl group to a nucleophilic substrate, e.g. RNH2 to form R-NH-CHO, which can undergo ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


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 prepared from the reaction of sodium ethoxide, formed in-situ from sodium and absolute ethanol, and chloroform: : CHCl3 + 3 Na + 3 EtOH → HC(OEt)3 + H2 + 3 NaCl Triethyl orthoformate is used in the Bodroux-Chichibabin aldehyde synthesis, for example: : RMgBr + HC(OC2H5)3 → RC(H)(OC2H5)2 + MgBr(OC2H5) : RC(H)(OC2H5)2 + H2O → RCHO + 2 C2H5OH In coordination chemistry, it is used to convert metal aquo complexes to the corresponding ethanol complexes: : i(H2O)6BF4)2 + 6 HC(OC2H5)3 → i(C2H5OH)6BF4)2 + 6 HC(O)(OC2H5) + 6 HOC2H5 Triethyl orthoformate (TEOF) is an excellent reagent for converting compatible carboxylic acids to ethyl esters. Such carboxylic acids, refluxed neat in excess TEOF until low-boiler ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


picture info

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 light, volatile, colourless, flammable liquid with a distinctive alcoholic odour similar to that of ethanol (potable alcohol). A polar solvent, methanol acquired the name wood alcohol because it was once produced chiefly by the destructive distillation of wood. Today, methanol is mainly produced industrially by hydrogenation of carbon monoxide. Methanol consists of a methyl group linked to a polar hydroxyl group. With more than 20 million tons produced annually, it is used as a precursor to other commodity chemicals, including formaldehyde, acetic acid, methyl tert-butyl ether, methyl benzoate, anisole, peroxyacids, as well as a host of more specialised chemicals. Occurrence Small amounts of methanol are present in normal, healthy hu ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


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 polymers). The compound is closely related and convertible to the industrially significant derivatives paraformaldehyde (), formaldehyde (), and 1,3,5-trioxane (). Methanediol is a product of the hydration of formaldehyde. The equilibrium constant for hydration is estimated to be 103, Eric V. Anslyn, Dennis A. Dougherty (2006)''Modern physical organic chemistry'' University Science Books. . 1095 pages predominates in dilute (<0.1%) solution. In more concentrated solutions, it oligomerizes to .


Occurrence

The dianion, methanediolate, is believed to be an intermediate in the crossed