Diglyme

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Diglyme
File:Diglyme.png
style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers
CAS number 111-96-6 YesY
PubChem 8150
ChemSpider 7858, 13839575
EC number 203-924-4
SMILES Script error: No such module "collapsible list".
style="background: #F8EABA; text-align: center;" colspan="2" | 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
style="background: #F8EABA; text-align: center;" colspan="2" | Hazards
Main hazards Flammable
 YesY (what is this?)  (verify)
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.

File:LiDiDiglyme PM3.png
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.

References

fr:Diglyme lv:Diglims nl:Diglyme ja:ジグリム pt:Diglima