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1,2-dimethoxyethane

Dimethoxyethane
Skeletal formula of dimethoxyethane
Ball-and-stick model of the dimethoxyethane molecule
Names
IUPAC name
1,2-Dimethoxyethane
Other names
DME, glyme, Ethylene glycol dimethyl ether, monoglyme,
dimethyl glycol,
dimethyl cellosolve
Identifiers
110-71-4 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:42263 N
ChemSpider 13854808 YesY
ECHA InfoCard 100.003.451
RTECS number KI1451000
Properties
C4H10O2
Molar mass 90.12 g·mol−1
Appearance Colorless liquid
Density 0.8683 g/cm3
Melting point −58 °C (−72 °F; 215 K)
Boiling point 85 °C (185 °F; 358 K)
miscible
Hazards
Flammable (F)
Toxic (T)
Repr. Cat. 2
R-phrases R60, R61, R11, R19, R20
S-phrases S53, S45
NFPA 704
Flammability code 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g., diesel fuel Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point −2 °C (28 °F; 271 K)
Related compounds
Related Ethers
Dimethoxymethane
Related compounds
 Ethylene glycol
1,4-Dioxane
Diethylene glycol dimethyl ether
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YesYN ?)
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, especially in batteries. Dimethoxyethane is miscible with water.


Monoglyme may be manufactured by a number of methods:

Together with a high-permittivity solvent (e.g. propylene carbonate), dimethoxyethane is used as the low-viscosity component of the solvent for electrolytes of lithium batteries. In the laboratory, DME is used as a coordinating solvent.

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 couplings. Dimethoxyethane is also a good solvent for oligo- and polysaccharides.


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Wikipedia

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