Dimethoxyethane

Dimethoxyethane
Names
	Preferred IUPAC name 1,2-Dimethoxyethane
	Other names Ethane-1,2-diyl dimethyl ether; DME; Glyme; Ethylene glycol dimethyl ether; Monoglyme; Dimethyl glycol; Dimethyl cellosolve
Identifiers
CAS Number	110-71-4 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:42263 ;
ChemSpider	13854808 ;
ECHA InfoCard	100.003.451
PubChem CID	8071;
RTECS number	KI1451000;
UNII	GXS24JF5IW ;
CompTox Dashboard (EPA)	DTXSID2027838 DTXSID0025286, DTXSID2027838 ;
	InChI InChI=1S/C4H10O2/c1-4(5-2)6-3/h4H,1-3H3 Key: SPEUIVXLLWOEMJ-UHFFFAOYSA-N ; InChI=1/C4H10O2/c1-4(5-2)6-3/h4H,1-3H3 Key: SPEUIVXLLWOEMJ-UHFFFAOYAV;
	SMILES COCCOC;
Properties
Chemical formula	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)
Solubility in water	miscible
Hazards
NFPA 704 (fire diamond)	2 2 0
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). verify (what is ?) Infobox references

Dimethoxyethane, also known as glyme, monoglyme, dimethyl glycol, ethylene glycol dimethyl ether, dimethyl cellosolve, and DME, is a colorless, aprotic, and liquid ether that is used as a solvent, especially in batteries.^[2] Dimethoxyethane is miscible with water.

Production

Monoglyme can in principle be produced by a number of methods.^[3] In practice it is produced industrially by the reaction of dimethylether with ethylene oxide.^[4] Other methods include:

CH₃OCH₃ + CH₂CH₂O → CH₃OCH₂CH₂OCH₃

via the Williamson ether synthesis — reacting the sodium salt of 2-methoxyethanol (previously prepared by reaction with sodium) with chloromethane:

2 CH₃OCH₂CH₂OH + 2 Na → 2 CH₃OCH₂CH₂ONa + H₂↑

CH₃OCH₂CH₂ONa + CH₃Cl → CH₃OCH₂CH₂OCH₃ + NaCl

via the alkylation of 2-methoxyethanol with dimethyl sulfate

Applications as solvent and ligand

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.

References

^ ^a ^b Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 704. doi:10.1039/9781849733069-00648. ISBN 978-0-85404-182-4.
^ D. Berndt, D. Spahrbier, "Batteries" in Ullmann’s Encyclopedia of Industrial Chemistry 2005, Wiley-VCH, Weinheim. doi:10.1002/14356007.a03_343
^ Dimethoxyethane
^ "Ethylene Glycol". Ullmann’s Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. 2000. doi:10.1002/14356007.a10_101. ISBN 3527306730. {{cite encyclopedia}}: Unknown parameter |authors= ignored (help)

External links

[iupac2013-1] Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 704. doi:10.1039/9781849733069-00648. ISBN 978-0-85404-182-4.

[2] D. Berndt, D. Spahrbier, "Batteries" in Ullmann’s Encyclopedia of Industrial Chemistry 2005, Wiley-VCH, Weinheim. doi:10.1002/14356007.a03_343

[3] Dimethoxyethane

[4] "Ethylene Glycol". Ullmann’s Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. 2000. doi:10.1002/14356007.a10_101. ISBN 3527306730. {{cite encyclopedia}}: Unknown parameter |authors= ignored (help)

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