Diglyme


Diglyme, or bis ether, is a solvent with a high boiling point. It is an organic compound which is the dimethyl ether of diethylene glycol. It is a colorless liquid with a slight ether-like odor. It is miscible with water as well as organic solvents.
It is prepared by a reaction of dimethyl ether and ethylene oxide over an acid catalyst.

Solvent

Because of its resiliance to strong bases, diglyme is favored as a solvent for reactions of alkali metal reagents even at high temperatures. Therefore, reactions involving organometallic reagents, such as Grignard reactions or metal hydride reductions, may have significantly enhanced reaction rates.
Diglyme is also used as a solvent in hydroboration reactions with diborane.
It serves as a chelate for alkali metal cations, leaving anions more active.

Safety

The European Chemicals Agency lists diglyme as a Substances of Very High Concern as a Reproductive Toxin.