Dimethoxymethane

Dimethoxymethane, also called methylal, is a clear colorless flammable liquid with a low boiling point, low viscosity and an excellent dissolving power. It has a chloroform-like odor and a pungent taste. It is the dimethyl acetal of formaldehyde. Dimethoxymethane is soluble in three parts water and miscible with most common organic solvents.

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It can be manufactured by oxidation of methanol or by the reaction of formaldehyde with methanol. In aqueous acid, it is hydrolyzed back to formaldehyde and methanol.

It is primarily used as a solvent and in the manufacture of perfumes, resins, adhesives, paint strippers and protective coatings.

Due to the anomeric effect, dimethoxymethane has a preference toward the gauche conformation around the C–O bonds, instead of the anti conformation. Since it is one of the smallest molecules exhibiting this effect, which has great interest in carbohydrate chemistry, dimethoxymethane is often used for theoretical studies of the anomeric effect.

References

• Merck Index, 11th Edition, 5936