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Tetramethoxymethane

Chemical compound From Wikipedia, the free encyclopedia

Tetramethoxymethane
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Tetramethoxymethane is a chemical compound which is formally formed by complete methylation of the hypothetical orthocarbonic acid C(OH)4.

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Preparation

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]

TMOC from chloropicrin corr

Because of the extreme toxicity of 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 disulfide and chlorine) was used:[3][4]

TMOC from trichlorsulfenylchloride

A less problematic synthesis is based on trichloroacetonitrile:[5][6]

TMOC from Trichloracetonitril

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]

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Properties

Tetramethoxymethane is a clear, colorless, aromatic-smelling, low-viscosity liquid which is stable against peroxide formation.[9]

Use

In addition to its use as a solvent, tetramethoxymethane is also 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]

Aminobenzoxazole aus Orthocarbonaten

Depending on the substituents, the one pot reaction proceeds in "modest to excellent" yields.

References

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