My watch list
my.chemeurope.com  
Login  

Dimethoxyethane



Dimethoxyethane
IUPAC name 1,2-Dimethoxyethane
Other names DME, glyme, monoglyme,
dimethyl glycol,
ethylene glycol dimethyl ether,
dimethyl cellosolve
Identifiers
CAS number 110-71-4
RTECS number KI1451000
SMILES COCCOC
Properties
Molecular formula C4H10O2
Molar mass 90.12 g/mol
Appearance colorless liquid
Density 0.8683 g/cm3, liquid
Melting point

-58 °C

Boiling point

85 °C

Solubility in water miscible
Hazards
EU classification Flammable (F)
Toxic (T)
Repr. Cat. 2
R-phrases R60, R61, R11, R19, R20
S-phrases S53, S45
Flash point −2 °C
Related Compounds
Related Ethers Dimethoxymethane
Related compounds Ethylene glycol
1,4-Dioxane
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Dimethoxyethane, also known as glyme, monoglyme, dimethyl glycol, ethylene glycol dimethyl ether, dimethyl cellosolve, and DME, is a clear, colorless, aprotic, and liquid ether that is used as a solvent. Dimethoxyethane is highly soluble in water.

Additional recommended knowledge

Dimethoxyethane is often used as a higher boiling alternative to diethyl ether and THF. Dimethoxyethane forms chelate complexes with cations and acts as a bidentate ligand. It is therefore often used in organometallic chemistry like Grignard reactions, hydride reductions, and palladium catalyzed reactions like Suzuki reactions and Stille coupling. Dimethoxyethane is also a good solvent for oligo- and polysaccharides.

The lowest energy form of dimethoxy ethane in the gas phase is the gauche, rather than the anti conformer

Production

Monoglyme be manufactured by a number of methods:[1]

2 CH3OCH2CH2OH + 2 Na → 2 CH3OCH2CH2ONa + H2
CH3OCH2CH2ONa + CH3Cl → CH3OCH2CH2OCH3 + NaCl
CH3OCH3 + CH2CH2O → CH3OCH2CH2OCH3

Uses

Together with a high-permittivity chemical (eg. propylene carbonate), dimethoxyethane is used as the low-viscosity component of the solvent for electrolytes of lithium batteries.

References

  1. ^ Dimethoxyethane
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Dimethoxyethane". A list of authors is available in Wikipedia.
Your browser is not current. Microsoft Internet Explorer 6.0 does not support some functions on Chemie.DE