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Diglyme



Diglyme
IUPAC name Bis(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 disclaimer and 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.

Additional recommended knowledge

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

  • Merck Index, 11th Edition, 3148.
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Diglyme". A list of authors is available in Wikipedia.
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