Editing Dimethoxyethane

{{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
|PIN = 1,2-Dimethoxyethane<ref name=iupac2013>{{cite book | title =  Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = [[Royal Society of Chemistry|The Royal Society of Chemistry]] | date = 2014 | location = Cambridge | page = 704 | doi = 10.1039/9781849733069-00648 | isbn = 978-0-85404-182-4}}</ref>
|OtherNames = Ethane-1,2-diyl dimethyl ether<ref name=iupac2013/><br />DME<br />Glyme<br />Ethylene glycol dimethyl ether<br />Monoglyme<br />Dimethyl glycol<br />Dimethyl cellosolve
|Section1={{Chembox Identifiers
|CASNo_Ref = {{cascite|correct|CAS}}
|CASNo = 110-71-4
|Abbreviations = DME
|Beilstein = 1209237
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|ChemSpiderID = 13854808
|ChEBI_Ref = {{ebicite|changed|EBI}}
|ChEBI = 42263
|EC_number = 203-794-9
|Gmelin = 1801
|UNII_Ref = {{fdacite|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
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|StdInChI = 1S/C4H10O2/c1-4(5-2)6-3/h4H,1-3H3
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
|StdInChIKey = SPEUIVXLLWOEMJ-UHFFFAOYSA-N
}}
|Section2={{Chembox Properties
|C=4 | H=10 | O=2
|Appearance = Colorless liquid
|Density = 0.8683 g/cm<sup>3</sup>
|Solubility = miscible
|MeltingPtC = -58
|BoilingPtC = 85
}}
|Section7={{Chembox Hazards 
|NFPA-H = 2
|NFPA-F = 2
|NFPA-R = 0
|GHSPictograms = {{GHS02}}{{GHS07}}{{GHS08}}
|GHSSignalWord = Danger
|HPhrases = {{H-phrases|225|332|360FD}}
|PPhrases = {{P-phrases|201|202|210|233|240|241|242|243|261|271|280|281|303+361+353|304+312|304+340|308+313|312|370+378|403+235|405|501}}
|FlashPtC = &minus;2
}}
|Section8={{Chembox Related
|OtherFunction_label = [[Ether]]s
|OtherFunction = [[Dimethoxymethane]]
|OtherCompounds = [[Ethylene glycol]]<br />[[Dioxane|1,4-Dioxane]]<br />[[Diethylene 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.<ref>D. Berndt, D. Spahrbier, "Batteries" in Ullmann's Encyclopedia of Industrial Chemistry 2005, Wiley-VCH, Weinheim. {{doi|10.1002/14356007.a03_343}}</ref> Dimethoxyethane is [[miscible]] with [[Water (molecule)|water]].

==Production==
Monoglyme is produced industrially by the reaction of [[dimethylether]] with [[ethylene oxide]]:<ref>{{cite encyclopedia|author=Siegfried Rebsdat |author2=Dieter Mayer |chapter=Ethylene Glycol|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|year=2000|publisher=Wiley-VCH|place=Weinheim|doi=10.1002/14356007.a10_101|isbn=3-527-30673-0}}</ref><ref>[http://chemindustry.ru/Dimethoxyethane.php Dimethoxyethane]</ref>
:CH<sub>3</sub>OCH<sub>3</sub> + CH<sub>2</sub>CH<sub>2</sub>O → CH<sub>3</sub>OCH<sub>2</sub>CH<sub>2</sub>OCH<sub>3</sub>

==Applications as solvent and ligand==
[[file:NbCl3(dme)(hexyne).png|thumb|left|144px|Structure of the [[coordination complex]] NbCl<sub>3</sub>(dimethoxyethane)(3-hexyne).<ref>{{cite journal |doi=10.1021/ja8100837|title=New Tantalum Ligand-Free Catalyst System for Highly Selective Trimerization of Ethylene Affording 1-Hexene: New Evidence of a Metallacycle Mechanism|year=2009|last1=Arteaga-Müller|first1=Rocío|last2=Tsurugi|first2=Hayato|last3=Saito|first3=Teruhiko|last4=Yanagawa|first4=Masao|last5=Oda|first5=Seiji|last6=Mashima|first6=Kazushi|journal=Journal of the American Chemical Society|volume=131|issue=15|pages=5370–5371|pmid=20560633}}</ref>]]
Together with a high-[[permittivity]] solvent (e.g. [[propylene carbonate]]), dimethoxyethane is used as the low-[[viscosity]] component of the solvent for [[electrolyte]]s of [[lithium battery|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 reaction]]s and [[Reductions with metal alkoxyaluminium hydrides|hydride reduction]]s are typical application. It is also suitable for [[palladium-catalyzed reactions]] including [[Suzuki reaction]]s and [[Stille coupling]]s.  Dimethoxyethane is also a good solvent for [[oligosaccharides|oligo]]- and [[polysaccharide]]s.

[[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.<ref>{{cite web |title=Tetra-Etch FAQ |url=https://weiserindustries.com/tetra-etch-faq |website=Weiser Industries USA Inc. |access-date=29 March 2023}}</ref>

==References==
<references/>

==External links==
* [https://web.archive.org/web/20070210004803/http://www.glymes.com/ Clariant Glymes Homepage www.glymes.com]
* [http://chemindustry.ru/Dimethoxyethane.php 1,2-Dimethoxyethane - chemical product info: properties, production, applications.]
* [http://www.inchem.org/documents/icsc/icsc/eics1568.htm International Chemical Safety Card 1568]
* [https://archive.today/20130417072001/http://www.evol.nw.ru/labs/lab38/spirov/hazard/1_2-dimethoxyethane.html Chemical hazard links]

[[Category:Glycol ethers]]
[[Category:Ether solvents]]
[[Category:Ligands]]