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| Names | |
|---|---|
| Preferred IUPAC name 1,2-Dimethoxyethane[1] | |
| Other names Ethane-1,2-diyl dimethyl ether[1] DME Glyme Ethylene glycol dimethyl ether Monoglyme Dimethyl glycol Dimethyl cellosolve | |
| Identifiers | |
| |
3D model (JSmol) | |
| Abbreviations | DME |
| 1209237 | |
| ChEBI | |
| ChemSpider |
|
| ECHA InfoCard | 100.003.451 |
| EC Number |
|
| 1801 | |
| RTECS number |
|
| UNII | |
| |
| |
| Properties | |
| C4H10O2 | |
| Molar mass | 90.122 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 | |
| GHS labelling: | |
   | |
| Danger | |
| H225,H332,H360FD | |
| P201,P202,P210,P233,P240,P241,P242,P243,P261,P271,P280,P281,P303+P361+P353,P304+P312,P304+P340,P308+P313,P312,P370+P378,P403+P235,P405,P501 | |
| NFPA 704 (fire diamond) | |
| Flash point | −2 °C (28 °F; 271 K) |
| Related compounds | |
RelatedEthers | Dimethoxymethane |
Related compounds | Ethylene glycol 1,4-Dioxane Diethylene glycol dimethyl ether |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Dimethoxyethane, also known asglyme,monoglyme,dimethyl glycol,ethylene glycol dimethyl ether,dimethyl cellosolve, andDME, is a colorless,aprotic, and liquidether that is used as asolvent, especially in batteries.[2] Dimethoxyethane ismiscible withwater.
Monoglyme is produced industrially by the reaction ofdimethylether withethylene oxide:[3][4]
(hexyne).png)
Together with a high-permittivity solvent (e.g.propylene carbonate), dimethoxyethane is used as the low-viscosity component of the solvent forelectrolytes oflithium batteries. In the laboratory, DME is used as a coordinating solvent.
Dimethoxyethane is often used as a higher-boiling-point alternative todiethyl ether andtetrahydrofuran. Dimethoxyethane acts as a bidentateligand for some metal cations. It is therefore often used inorganometallic chemistry.Grignard reactions andhydride reductions are typical application. It is also suitable forpalladium-catalyzed reactions includingSuzuki reactions andStille couplings. Dimethoxyethane is also a good solvent foroligo- andpolysaccharides.
Sodium naphthalide dissolved in dimethoxyethane is used as aPTFE etching solution that removes fluorine atoms from the surface, which get replaced by oxygen, hydrogen, and water. This physically etches the surface as well to prepare the surface for better adhesion.[6]
