Tetramethoxymethane is a

chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...

which is formally formed by complete

methylation Methylation, in the chemistry, chemical sciences, is the addition of a methyl group on a substrate (chemistry), substrate, or the substitution of an atom (or group) by a methyl group. Methylation is a form of alkylation, with a methyl group replac ...

of the hypothetical

orthocarbonic acid Orthocarbonic acid, carbon hydroxide, or 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 hydroxyl groups. It would be therefore a ...

Preparation

The obvious synthetic route from the tetrahalomethanes does not yield the desired product, instead giving orthoformates and a halohydrin byproduct.R. H. De Wolfe, ''Carboxylic ortho acid derivatives: preparation and synthetic applications'', Organic Chemistry, Vol. 14, Academic Press, Inc. New York – London, 1970, . The original preparation of the tetramethoxymethane was therefore based on

chloropicrin Chloropicrin, also known as PS (from Port Sunlight) and nitrochloroform, is a chemical compound currently used as a broad-spectrum antimicrobial, fungicide, herbicide, insecticide, and nematicide. It was used as a poison gas in World War I and the ...

: :

Because of the extreme toxicity of chloropicrin, other tetrasubstituted reactive methane derivatives were investigated as starting material for tetramethoxymethane. For example,

trichloromethanesulfenyl chloride Trichloromethane sulfenyl chloride or perchloromethyl mercaptan is the organosulfur compound with the formula . It is mainly used as an intermediate for the synthesis of dyes and fungicides (captan, folpet). It is a colorless oil, although commerc ...

(also used as a

chemical warfare agent A chemical weapon (CW) is a specialized munition that uses chemicals formulated to inflict death or harm on humans. According to the Organisation for the Prohibition of Chemical Weapons (OPCW), this can be any chemical compound intended as a ...

and easily accessible from

carbon disulfide Carbon disulfide (also spelled as carbon disulphide) is an inorganic compound with the chemical formula and structure . It is also considered as the anhydride of thiocarbonic acid. It is a colorless, flammable, neurotoxic liquid that is used as ...

and

chlorine Chlorine is a chemical element; it has Symbol (chemistry), symbol Cl and atomic number 17. The second-lightest of the halogens, it appears between fluorine and bromine in the periodic table and its properties are mostly intermediate between ...

) was used:H. Tieckelmann, H. W. Post, ''The preparation of methyl, ethyl, propyl, and butyl orthocarbonates'', J. Org. Chem., 13 (2), 265-267 (1948), . : TMOC from trichlorsulfenylchloride

A less problematic synthesis is based on

trichloroacetonitrile Trichloroacetonitrile is an organic compound with the formula CCl3CN. It is a colourless liquid, although commercial samples often are brownish. It is used commercially as a precursor to the fungicide etridiazole. It is prepared by dehydration of ...

: :

Thallium Thallium is a chemical element; it has Symbol (chemistry), symbol Tl and atomic number 81. It is a silvery-white post-transition metal that is not found free in nature. When isolated, thallium resembles tin, but discolors when exposed to air. Che ...

methoxide reacts with

to give tetramethoxymethane and

thallium sulfide Thallium(I) sulfide, Tl2S, is a chemical compound of thallium and sulfur. Occurrence Tl2S is found in nature as the mineral carlinite which has the distinction of being the only sulfide mineral of thallium that does not contain at least two met ...

; likewise dimethyl dibutylstannate gives tetramethoxymethane and dibutyltin sulfide. Further preparative methods are described in the literature.W. Kantlehner et al., ''Die präparative Chemie der O- und N-funktionellen Orthokohlensäure-Derivate'',

Synthesis Synthesis or synthesize may refer to: Science Chemistry and biochemistry *Chemical synthesis, the execution of chemical reactions to form a more complex molecule from chemical precursors **Organic synthesis, the chemical synthesis of organi ...

; 1977(2): 73-90, . Synthesis from chloropicrin only yields about 50% product. Syntheses from trichloromethanesulfenyl chloride or trichloroacetonitrile or the thallium-sulfide route yield about 70-80% product, but the tin-sulfide synthesis has a 95% yield.

Properties

Tetramethoxymethane is a clear, colorless, aromatic-smelling, low-viscosity liquid which is stable against peroxide formation.

Use

In addition to its use as a

solvent A solvent (from the Latin language, Latin ''wikt:solvo#Latin, solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a Solution (chemistry), solution. A solvent is usually a liquid but can also be a solid, a gas ...

, tetramethoxymethane is also used as a fuel in

polymer fuel cell Proton-exchange membrane fuel cells (PEMFC), also known as polymer electrolyte membrane (PEM) fuel cells, are a type of fuel cell being developed mainly for transport applications, as well as for stationary fuel-cell applications and portable fu ...

s, as an

alkylating agent Alkylation is a chemical reaction that entails transfer of an alkyl group. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effecting ...

at elevated temperatures (180-200 °C), as a transesterification reagent (but showing less reactivity than trimethoxymethane), and as a reagent for the synthesis of 2-aminobenzoxazoles, which are used as molecular building blocks in pharmaceutical active ingredients used in

neuroleptics Antipsychotics, previously known as neuroleptics and major tranquilizers, are a class of psychotropic medication primarily used to manage psychosis (including delusions, hallucinations, paranoia or disordered thought), principally in schizoph ...

sedative A sedative or tranquilliser is a substance that induces sedation by reducing irritability or Psychomotor agitation, excitement. They are central nervous system (CNS) Depressant, depressants and interact with brain activity, causing its decelera ...

antiemetic An antiemetic is a drug that is effective against vomiting and nausea. Antiemetics are typically used to treat motion sickness and the side effects of opioid analgesics, general anaesthetics, and chemotherapy directed against cancer. They may ...

muscle relaxant A muscle relaxant is a drug that affects skeletal muscle function and decreases the muscle tone. It may be used to alleviate symptoms such as muscle spasms, pain, and hyperreflexia. The term "muscle relaxant" is used to refer to two major therapeu ...

fungicide Fungicides are pesticides used to kill parasitic fungi or their spores. Fungi can cause serious damage in agriculture, resulting in losses of yield and quality. Fungicides are used both in agriculture and to fight fungal infections in animals, ...

s and others.C. L. Cioffi et al., ''Synthesis of 2-Aminobenzoxazoles Using Tetramethyl Orthocarbonate or 1,1-Dichloro-diphenoxymethane'', J. Org. Chem., 75 (2), 7942-7945 (2010), {{doi, 10.1021/jo1017052. Depending on the substituents, the one pot reaction proceeds in "modest to excellent" yields.

References

Orthocarbonates Methoxy compounds