Diglyme

Diglyme
Preferred IUPAC name

Diglyme
Systematic name

1-methoxy-2-(2-methoxyethoxy)ethane
Other names

2-Methoxyethyl ether; Di(2-methoxyethyl) ether; Diethylene glycol dimethyl ether
Identifiers
CAS number 111-96-6 Y
PubChem 8150
ChemSpider 13839575 Y
UNII M4BH3X0MVZ Y
EC number 203-924-4
DrugBank DB02935
ChEBI CHEBI:46784 Y
Jmol-3D images Image 1
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
EU classification Toxic (T)
Flammable (F)
R-phrases R60, R61, R10, R19
S-phrases S53, S45
Flash point 57 °C
Related compounds
Related compounds Diethylene glycol diethyl ether, ethylene glycol dimethyl ether
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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.

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.

References