Tetraethoxymethane is a chemical compound which is formally formed by complete ethylation of the hypothetical orthocarbonic acid C(OH)4 (orthocarbonic acid violates the Erlenmeyer rule and is unstable in free state).
Names | |
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Preferred IUPAC name
(Triethoxymethoxy)ethane | |
Other names
Tetraethyl orthocarbonate
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Identifiers | |
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3D model (JSmol)
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ChemSpider |
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ECHA InfoCard | 100.000.985 |
EC Number |
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PubChem CID
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UNII |
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CompTox Dashboard (EPA)
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Properties | |
C9H20O4 | |
Molar mass | 192.25 g·mol−1 |
Appearance | liquid |
Density | 0.919 |
Boiling point | 159.5 °C (319.1 °F; 432.6 K) |
Hazards | |
GHS labelling: | |
H226, H315, H319, H335 | |
Related compounds | |
Other cations
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Tetraethoxysilane |
Related compounds
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Tetramethoxymethane |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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Tetraethoxymethane was described the first time in 1864.[1]
The preparation of tetraethoxymethane from the highly toxic trichloronitromethane is known in the literature[1][2][3][4] and achieves only yields of 46-49[3] to 58%:[4]
The obvious synthetic route from tetrachloromethane does not provide the desired product, as in the homologous tetramethoxymethane.[5]
Starting from the less toxic trichloroacetonitrile (compared with trichloronitromethane), higher yields can be obtained (up to 85%).[6] An alternative reaction, bypassing problematic reactants, is the reaction of dialkyltin dialkoxides with carbon disulfide at elevated temperature in an autoclave:[7]
A more recent synthesis starts directly from sodium ethoxide, tin(IV)chloride, and carbon disulfide.[8]
Tetraethoxymethane is a water-clear, aromatic or fruity smelling,[9] liquid of low-viscosity which is unstable against strong acids and strong bases.[10]
Tetraethoxymethane can be used as a solvent and for the alkylation of CH-acidic compounds (e.g. phenols and carboxylic acids). In addition, it reacts with amines, enol ethers and sulfonamides,[11] whereby spiro compounds can also be obtained. Spiro orthocarbonates (SOCs)[12] are of some industrial interest, as they are used as additives for reducing shrinkage during the polymerization of epoxides (they are used as expanding monomers).[13]