Diglyme
IUPAC name	Di(2-methoxyethyl) ether
Other names	Diglyme; 2-methoxyethyl ether; diethylene glycol dimethyl ether
Identifiers
CAS number	111-96-6
SMILES	COCCOCCOC
Properties
Molecular formula	C6H14O3
Molar mass	134.18 g/mol
Density	0.937 g/mL
Melting point	-64 °C
Boiling point	162 °C
Solubility in water	miscible
Hazards
Main hazards	Flammable
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Diglyme, or bis(2-methoxyethyl) ether, is a solvent with a high boiling point. It is an organic compound which is the dimethyl ether of diethylene glycol. (The name "diglyme" is a portmanteau of "diglycol methyl ether.") It is a clear, colorless liquid with a slight ether-like odor. It is miscible with water, alcohols, diethyl ether, and hydrocarbon solvents.

Diglyme is mainly used as a solvent in organic reactions. It has the ability to chelate small cations, leaving anions more active. Therefore, reactions involving organometallic reagents, such as Grignard reactions or metal hydride reductions, may have significantly enhanced reaction rates.

A lithium cation being chelated by a diglyme molecule

Diglyme is also used as a solvent in hydroboration reactions with diborane.

Its stability, even at high pH values, makes it an excellent solvent for reactions with strong bases or reactions that require high temperatures.

[edit] References

• Merck Index, 11th Edition, 3148.