What is 1,2-dimethyloxyethane?

1,2-dimethyloxyethane, also known as glyme, monoglyme, dimethyl glycol, ethylene glycol dimethyl ether, dimethyl cellosolve, and DME, is a colorless, aprotic, and liquid ether that is used as a solvent, especially in batteries.1,2-dimethyloxyethane is miscible with water.

Solubility

Miscible with water, methanol, ethanol, diethyl ether, acetone, tetrahydrofuran, benzene and toluene. 

Production

Monoglyme is produced industrially by the reaction of dimethylether with ethylene oxide:

CH3OCH3 + CH2CH2O → CH3OCH2CH2OCH3

Applications

Applications as solvent and ligand

Together with a high-permittivity solvent (e.g. propylene carbonate), 1,2-dimethyloxyethane is used as the low-viscosity component of the solvent for electrolytes of lithium batteries. In the laboratory, DME is used as a coordinating solvent.

1,2-dimethyloxyethane is often used as a higher boiling alternative to diethyl ether and THF. 1,2-dimethyloxyethane acts as a bidentate ligand for some metal cations. It is therefore often used in organometallic chemistry. Grignard reactions and hydride reductions are typical application. It is also suitable for palladium-catalyzed reactions including Suzuki reactions and Stille couplings. 1,2-dimethyloxyethane is also a good solvent for oligo- and polysaccharides.