Names | |
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Preferred IUPAC name Tetramethoxymethane | |
Other names Tetramethyl orthocarbonate | |
Identifiers | |
3D model (JSmol) | |
ChemSpider | |
ECHA InfoCard | 100.015.853 |
EC Number |
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PubChem CID | |
UNII | |
UN number | 3272 |
CompTox Dashboard (EPA) | |
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Properties | |
C5H12O4 | |
Molar mass | 136.15 g·mol −1 |
Appearance | colourless liquid [1] |
Density | 1.023 g/cm3 (25 °C) |
Melting point | −5.5 °C [1] |
Boiling point | 114 °C [1] |
Hazards | |
GHS labelling: | |
Danger | |
H225, H315, H319, H335 | |
P210, P261, P305+P351+P338 | |
Related compounds | |
Other cations | Tetramethoxysilane |
Related compounds | Tetraethoxymethane |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Tetramethoxymethane is a chemical compound which is formally formed by complete methylation of the hypothetical orthocarbonic acid C(OH)4.
The obvious synthetic route from the tetrahalomethanes does not yield the desired product, instead giving orthoformates and a halohydrin byproduct. [2] : 13 The original preparation of the tetramethoxymethane was therefore based on chloropicrin: [1]
Because of the unpleasant properties of the chloropicrin, other tetrasubstituted reactive methane derivatives were investigated as starting material for tetramethoxymethane. For example, trichloromethanesulfenyl chloride (also used as a chemical warfare agent and easily accessible from carbon bisulfide and chlorine) was used: [3] [4]
A less problematic synthesis is based on trichloroacetonitrile: [5] [6]
Thallium methoxide reacts with carbon disulfide to give tetramethoxymethane and thallium sulfide; [7] likewise dimethyl dibutylstannate gives tetramethoxymethane and dibutyltin sulfide. [8] Further preparative methods are described in the literature. [7]
Synthesis from chloropicrin only yields about 50% product. Syntheses from trichloromethanesulfenyl chloride or trichloroacetonitrile or the thallium-sulfide route yield about 70-80% product, [3] [7] but the tin-sulfide synthesis has a 95% yield. [8]
Tetramethoxymethane is water-clear, aromatic-smelling, low-viscosity liquid which is stable against peroxide formation. [9]
In addition to the use as a solvent, tetramethoxymethane is used as a fuel in polymer fuel cells, [10] as an alkylating agent at elevated temperatures (180-200 °C) [11] as a transesterification reagent (but showing less reactivity than trimethoxymethane [2] ) and as a reagent for the synthesis of 2-aminobenzoxazoles, which are used as molecular building blocks in pharmaceutical active ingredients used in neuroleptics, sedatives, antiemetics, muscle relaxants, fungicides and others. [12]
Depending on the substituents, the one pot reaction proceeds in "modest to excellent" yields.
Hydrogen peroxide–urea is a white crystalline solid chemical compound composed of equal amounts of hydrogen peroxide and urea. It contains solid and water-free hydrogen peroxide, which offers a higher stability and better controllability than liquid hydrogen peroxide when used as an oxidizing agent. Often called carbamide peroxide in dentistry, it is used as a source of hydrogen peroxide when dissolved in water for bleaching, disinfection and oxidation.
Organosulfur chemistry is the study of the properties and synthesis of organosulfur compounds, which are organic compounds that contain sulfur. They are often associated with foul odors, but many of the sweetest compounds known are organosulfur derivatives, e.g., saccharin. Nature is abound with organosulfur compounds—sulfur is vital for life. Of the 20 common amino acids, two are organosulfur compounds, and the antibiotics penicillin and sulfa drugs both contain sulfur. While sulfur-containing antibiotics save many lives, sulfur mustard is a deadly chemical warfare agent. Fossil fuels, coal, petroleum, and natural gas, which are derived from ancient organisms, necessarily contain organosulfur compounds, the removal of which is a major focus of oil refineries.
A xanthate is a salt or ester of a xanthic acid. The formula of the salt of xanthic acid is [R−O−CS2]−M+. Xanthate also refers to the anion [R−O−CS2]−. The formula of a xanthic acid is R−O−C(=S)−S−H, such as ethyl xanthic acid, while the formula of an ester of a xanthic acid is R−O−C(=S)−S−R', where R and R' are organyl groups. The salts of xanthates are also called O-organyl dithioates. The esters of xanthic acid are also called O,S-diorganyl esters of dithiocarbonic acid. The name xanthate is derived from Ancient Greek ξανθός (xanthos) meaning 'yellowish' or 'golden', and indeed most xanthate salts are yellow. They were discovered and named in 1823 by Danish chemist William Christopher Zeise. These organosulfur compounds are important in two areas: the production of cellophane and related polymers from cellulose and for extraction of certain sulphide bearing ores. They are also versatile intermediates in organic synthesis.
In organic chemistry, a sulfoxide, also called a sulphoxide, is an organosulfur compound containing a sulfinyl functional group attached to two carbon atoms. It is a polar functional group. Sulfoxides are oxidized derivatives of sulfides. Examples of important sulfoxides are alliin, a precursor to the compound that gives freshly crushed garlic its aroma, and dimethyl sulfoxide (DMSO), a common solvent.
Orthocarbonic acid, carbon hydroxide, methanetetrol is the name given to a hypothetical compound with the chemical formula H4CO4 or C(OH)4. Its molecular structure consists of a single carbon atom bonded to four hydroxyl groups. It would be therefore a fourfold alcohol. In theory it could lose four protons to give the hypothetical oxocarbon anion orthocarbonateCO4−4, and is therefore considered an oxoacid of carbon.
Tetraacetylethylenediamine, commonly abbreviated as TAED, is an organic compound with the formula (CH3C(O))2NCH2CH2N(C(O)CH3)2. This white solid is commonly used as a bleach activator in laundry detergents and for paper pulp. It is produced by acetylation of ethylenediamine.
The Dakin oxidation (or Dakin reaction) is an organic redox reaction in which an ortho- or para-hydroxylated phenyl aldehyde (2-hydroxybenzaldehyde or 4-hydroxybenzaldehyde) or ketone reacts with hydrogen peroxide (H2O2) in base to form a benzenediol and a carboxylate. Overall, the carbonyl group is oxidised, whereas the H2O2 is reduced.
Thiophosgene is a red liquid with the formula CSCl2. It is a molecule with trigonal planar geometry. There are two reactive C–Cl bonds that allow it to be used in diverse organic syntheses.
The tert-butyloxycarbonyl protecting group or tert-butoxycarbonyl protecting group is an acid-labile protecting group used in organic synthesis.
Methyl acrylate is an organic compound, more accurately the methyl ester of acrylic acid. It is a colourless liquid with a characteristic acrid odor. It is mainly produced to make acrylate fiber, which is used to weave synthetic carpets. It is also a reagent in the synthesis of various pharmaceutical intermediates. Owing to the tendency of methyl acrylate to polymerize, samples typically contain an inhibitor such as hydroquinone.
The Mukaiyama taxol total synthesis published by the group of Teruaki Mukaiyama of the Tokyo University of Science between 1997 and 1999 was the 6th successful taxol total synthesis. The total synthesis of Taxol is considered a hallmark in organic synthesis.
In organosulfur chemistry, thiosulfinate is a functional group consisting of the linkage R-S(O)-S-R. Thiolsulfinates are also named as alkanethiosulfinic acid esters.
DuPhos is a class of organophosphorus compound that are used ligands for asymmetric synthesis. The name DuPhos is derived from (1) the chemical company that sponsored the research leading to this ligand's invention, DuPont and (2) the compound is a diphosphine ligand type. Specifically it is classified as a C2-symmetric ligand, consisting of two phospholanes rings affixed to a benzene ring.
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.
In organic chemistry, a dithiol is a type of organosulfur compound with two thiol functional groups. Their properties are generally similar to those of monothiols in terms of solubility, odor, and volatility. They can be classified according to the relative location of the two thiol groups on the organic backbone.
Sulfinyl halide have the general formula R−S(O)−X, where X is a halogen. They are intermediate in oxidation level between sulfenyl halides, R−S−X, and sulfonyl halides, R−SO2−X. The best known examples are sulfinyl chlorides, thermolabile, moisture-sensitive compounds, which are useful intermediates for preparation of other sufinyl derivatives such as sulfinamides, sulfinates, sulfoxides, and thiosulfinates. Unlike the sulfur atom in sulfonyl halides and sulfenyl halides, the sulfur atom in sulfinyl halides is chiral, as shown for methanesulfinyl chloride.
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 trichloroacetamide. As a bifunctional compound, trichloroacetonitrile can react at both the trichloromethyl and the nitrile group. The electron-withdrawing effect of the trichloromethyl group activates the nitrile group for nucleophilic additions. The high reactivity makes trichloroacetonitrile a versatile reagent, but also causes its susceptibility towards hydrolysis.
N-Hydroxyphthalimide is the organic compound with the formula C6H4(CO)2NOH. A white or yellow solid, it is a derivative of phthalimide. The compound is as a catalyst in the synthesis of other organic compounds. It is soluble in water and organic solvents such as acetic acid, ethyl acetate and acetonitrile.
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