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;
Abbreviations	DME
Beilstein Reference	1209237
ChEBI	CHEBI:42263 ;
ChemSpider	13854808 ;
ECHA InfoCard	100.003.451
EC Number	203-794-9;
Gmelin Reference	1801
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
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H332, H360FD
Precautionary statements	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)	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 is produced industrially by the reaction of dimethylether with ethylene oxide:^[3]^[4]

CH₃OCH₃ + CH₂CH₂O → CH₃OCH₂CH₂OCH₃

Applications as solvent and ligand

Structure of the coordination complex NbCl₃(dimethoxyethane)(3-hexyne).^[5]

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-point alternative to diethyl ether and tetrahydrofuran. Dimethoxyethane acts as a bidentate ligand for some metal cations. It is therefore often used in organometallic chemistry. Grignard reactions and hydride reductions are typical application. It is also suitable for palladium-catalyzed reactions including Suzuki reactions and Stille couplings. Dimethoxyethane is also a good solvent for oligo- and polysaccharides.

Sodium naphthalide dissolved in dimethoxyethane is used as a PTFE 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]

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
^ Siegfried Rebsdat; Dieter Mayer (2000). "Ethylene Glycol". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_101. ISBN 3-527-30673-0.
^ Dimethoxyethane
^ Arteaga-Müller, Rocío; Tsurugi, Hayato; Saito, Teruhiko; Yanagawa, Masao; Oda, Seiji; Mashima, Kazushi (2009). "New Tantalum Ligand-Free Catalyst System for Highly Selective Trimerization of Ethylene Affording 1-Hexene: New Evidence of a Metallacycle Mechanism". Journal of the American Chemical Society. 131 (15): 5370–5371. doi:10.1021/ja8100837. PMID 20560633.
^ "Tetra-Etch FAQ". Weiser Industries USA Inc. Retrieved 29 March 2023.

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] Siegfried Rebsdat; Dieter Mayer (2000). "Ethylene Glycol". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_101. ISBN 3-527-30673-0.

[4] Dimethoxyethane

[5] Arteaga-Müller, Rocío; Tsurugi, Hayato; Saito, Teruhiko; Yanagawa, Masao; Oda, Seiji; Mashima, Kazushi (2009). "New Tantalum Ligand-Free Catalyst System for Highly Selective Trimerization of Ethylene Affording 1-Hexene: New Evidence of a Metallacycle Mechanism". Journal of the American Chemical Society. 131 (15): 5370–5371. doi:10.1021/ja8100837. PMID 20560633.

[6] "Tetra-Etch FAQ". Weiser Industries USA Inc. Retrieved 29 March 2023.

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