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{{distinguish|dimethoxymethane|dimethyl ether}}{{chembox|Verifiedfields = changed|Watchedfields = changed|verifiedrevid = 441023090|Name = Dimethoxyethane|ImageFile = 1,2-Dimethoxyethane.svg|ImageAlt = Skeletal formula of dimethoxyethane|ImageFile1 = Dimethoxyethane 3D ball.png|ImageAlt1 = Ball-and-stick model of the dimethoxyethane molecule

ROYAL SOCIETY OF CHEMISTRY>THE ROYAL SOCIETY OF CHEMISTRY

LOCATION = CAMBRIDGE

DOI = 10.1039/9781849733069-00648, 978-0-85404-182-4, |OtherNames = Ethane-1,2-diyl dimethyl etherDMEGlymeEthylene glycol dimethyl etherMonoglymeDimethyl glycolDimethyl cellosolve|Section1={{Chembox Identifiers

correct|CAS}}|CASNo = 110-71-4|Abbreviations = DME|Beilstein = 1209237

correct|chemspider}}|ChemSpiderID = 13854808

changed|EBI}}|ChEBI = 42263|EC_number = 203-794-9|Gmelin = 1801

correct|FDA}}|UNII = GXS24JF5IW|RTECS = KI1451000|PubChem = 8071|SMILES = COCCOC|InChI = 1/C4H10O2/c1-4(5-2)6-3/h4H,1-3H3|InChIKey = SPEUIVXLLWOEMJ-UHFFFAOYAV

correct|chemspider}}|StdInChI = 1S/C4H10O2/c1-4(5-2)6-3/h4H,1-3H3

correct|chemspider}}|StdInChIKey = SPEUIVXLLWOEMJ-UHFFFAOYSA-N}}|Section2={{Chembox Properties

H=10 | O=2|Appearance = Colorless liquid|Density = 0.8683 g/cm3|Solubility = miscible|MeltingPtC = -58|BoilingPtC = 85}}|Section7={{Chembox Hazards |NFPA-H = 2|NFPA-F = 2|NFPA-R = 0|GHSPictograms = {{GHS02}}{{GHS07}}{{GHS08}}|GHSSignalWord = Danger

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303+361+353

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403+235

501}}|FlashPtC = −2}}|Section8={{Chembox Related|OtherFunction_label = Ethers|OtherFunction = Dimethoxymethane

Ethylene glycolDioxane>1,4-DioxaneDiethylene glycol dimethyl ether}}}}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.D. Berndt, D. Spahrbier, “Batteries” in Ullmann’s Encyclopedia of Industrial Chemistry 2005, Wiley-VCH, Weinheim. {{doi|10.1002/14356007.a03_343}} Dimethoxyethane is miscible with water. Production Monoglyme is produced industrially by the reaction of dimethylether with ethylene oxide:ENCYCLOPEDIA, Siegfried Rebsdat, Dieter Mayer, Ethylene Glycol, Ullmann’s Encyclopedia of Industrial Chemistry, 2000, Wiley-VCH, Weinheim, 10.1002/14356007.a10_101, 3-527-30673-0, Dimethoxyethane CH3OCH3 + CH2CH2O → CH3OCH2CH2OCH3 Applications as solvent and ligand file:NbCl3(dme)(hexyne).png|thumb|left|144px|Structure of the (coordination complex]] NbCl3(dimethoxyethane)(3-hexyne).JOURNAL, 10.1021/ja8100837, New Tantalum Ligand-Free Catalyst System for Highly Selective Trimerization of Ethylene Affording 1-Hexene: New Evidence of a Metallacycle Mechanism, 2009, Arteaga-Müller, Rocío, Tsurugi, Hayato, Saito, Teruhiko, Yanagawa, Masao, Oda, Seiji, Mashima, Kazushi, Journal of the American Chemical Society, 131, 15, 5370–5371, 20560633, )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.WEB, Tetra-Etch FAQ,weiserindustries.com/tetra-etch-faq, Weiser Industries USA Inc., 29 March 2023, References External links www.glymes.com/" title="web.archive.org/web/20070210004803www.glymes.com/">Clariant Glymes Homepage www.glymes.com 1,2-Dimethoxyethane - chemical product info: properties, production, applications. International Chemical Safety Card 1568 www.evol.nw.ru/labs/lab38/spirov/hazard/1_2-dimethoxyethane.html" title="archive.today/20130417072001www.evol.nw.ru/labs/lab38/spirov/hazard/1_2-dimethoxyethane.html">Chemical hazard links