Dimethoxyethane

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Dimethoxyethane
Dimethoxyethane
style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers
CAS number 110-71-4 YesY
ChemSpider 7780
RTECS number KI1451000
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style="background: #F8EABA; text-align: center;" colspan="2" | 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
style="background: #F8EABA; text-align: center;" colspan="2" | Hazards
EU classification Flammable (F)
Toxic (T)
Repr. Cat. 2
R-phrases R60, R61, R11, R19, R20
S-phrases S53, S45
NFPA 704
3
2
2
Flash point −2 °C
style="background: #F8EABA; text-align: center;" colspan="2" | Related compounds
Related Ethers Dimethoxymethane
Related compounds Ethylene glycol
1,4-Dioxane
 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

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 miscible with water.

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 dimethoxyethane in the gas phase is the gauche, rather than the anti conformer.

Production

Monoglyme may 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

External links

es:1,2-dimetoxietano nl:1,2-dimethoxyethaan ja:1,2-ジメトキシエタン fi:Dimetoksietaani