From Wikipedia, the free encyclopedia
Jump to: navigation, search
Skeletal formula of diglyme
Space-filling model of the diglyme molecule
Preferred IUPAC name
Systematic IUPAC name
Other names
2-Methoxyethyl ether; Di(2-methoxyethyl) ether; Diethylene glycol dimethyl ether
111-96-6 YesY
ChEBI CHEBI:46784 YesY
ChemSpider 13839575 YesY
DrugBank DB02935 YesY
EC number 203-924-4
Jmol-3D images Image
PubChem 8150
Molar mass 134.18 g·mol−1
Density 0.937 g/mL
Melting point −64 °C (−83 °F; 209 K)
Boiling point 162 °C (324 °F; 435 K)
EU classification Toxic (T)
Flammable (F)
R-phrases R60 R61 R10 R19
S-phrases S53 S45
Flash point 57 °C (135 °F; 330 K)
Related compounds
Related compounds
Diethylene glycol diethyl ether, ethylene glycol dimethyl ether
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 YesY verify (what isYesY/N?)
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.

A lithium cation being chelated by a diglyme molecule

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.

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.


  • Merck Index, 11th Edition, 3148.