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{{chembox |
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{{chembox |
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|Watchedfields = changed |
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| verifiedrevid = 443684548 |
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|verifiedrevid = 443685984 |
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| ImageFile = Diglyme.png |
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| PIN = Diglyme |
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|ImageFile = Diglyme.png |
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|ImageAlt = Skeletal formula of diglyme |
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| SystematicName = 1-methoxy-2-(2-methoxyethoxy)ethane |
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|ImageFile1 = Diglyme 3D spacefill.png |
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| OtherNames = 2-Methoxyethyl ether; Di(2-methoxyethyl) ether; Diethylene glycol dimethyl ether |
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|ImageAlt1 = Space-filling model of the diglyme molecule |
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| Section1 = {{Chembox Identifiers |
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|PIN = 1-Methoxy-2-(2-methoxyethoxy)ethane<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 704 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}</ref> |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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|OtherNames = Diglyme<br />2-Methoxyethyl ether<br />Di(2-methoxyethyl) ether<br />Diethylene glycol dimethyl ether |
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| UNII = M4BH3X0MVZ |
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|Section1={{Chembox Identifiers |
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| InChI = 1/C6H14O3/c1-7-3-5-9-6-4-8-2/h3-6H2,1-2H3 |
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| InChIKey = SBZXBUIDTXKZTM-UHFFFAOYAG |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C6H14O3/c1-7-3-5-9-6-4-8-2/h3-6H2,1-2H3 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = SBZXBUIDTXKZTM-UHFFFAOYSA-N |
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| CASNo = 111-96-6 |
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| CASNo = 111-96-6 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| PubChem = 8150 |
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| Beilstein = 1736101 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 13839575 |
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| EINECS = 203-924-4 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB02935 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 46784 |
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| ChEBI = 46784 |
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| ChEMBL = 1234162 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 13839575 |
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| EINECS = 203-924-4 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB02935 |
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| Gmelin = 26843 |
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| PubChem = 8150 |
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| RTECS = KN3339000 |
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| UNNumber = 2252 1993 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = M4BH3X0MVZ |
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| SMILES = COCCOCCOC |
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| SMILES = COCCOCCOC |
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|InChI = 1/C6H14O3/c1-7-3-5-9-6-4-8-2/h3-6H2,1-2H3 |
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}} |
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|InChIKey = SBZXBUIDTXKZTM-UHFFFAOYAG |
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| Section2 = {{Chembox Properties |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| Formula = C<sub>6</sub>H<sub>14</sub>O<sub>3</sub> |
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|StdInChI = 1S/C6H14O3/c1-7-3-5-9-6-4-8-2/h3-6H2,1-2H3 |
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| MolarMass = 134.18 g/mol |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| Appearance = |
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|StdInChIKey = SBZXBUIDTXKZTM-UHFFFAOYSA-N |
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| Density = 0.937 g/mL |
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}} |
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| MeltingPt = -64 °C |
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|Section2={{Chembox Properties |
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| BoilingPt = 162 °C |
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|Formula = {{chem2|(CH3OCH2CH2)2O}} |
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| Solubility = miscible |
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|C=6|H=14|O=3 |
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}} |
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|Density = 0.937 g/mL |
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| Section3 = {{Chembox Hazards |
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|MeltingPtC = -64 |
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| FlashPt = 57°C |
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|BoilingPtC = 162 |
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| EUClass = Toxic ('''T''') </br>Flammable ('''F''') |
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|Solubility = Miscible |
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| RPhrases = {{R60}}, {{R61}}, {{R10}}, {{R19}} |
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}} |
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| SPhrases = {{S53}}, {{S45}} |
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| Hazards = |
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|Section7={{Chembox Hazards |
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|FlashPtC = 57 |
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}} |
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| GHSPictograms = {{GHS02}}{{GHS08}} |
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| GHSSignalWord = Danger |
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| HPhrases = {{H-phrases|226|360}} |
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| PPhrases = {{P-phrases|201|202|210|233|240|241|242|243|280|281|303+361+353|308+313|370+378|403+235|405|501}} |
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}} |
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|Section9={{Chembox Related |
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|OtherCompounds = ], ]}} |
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}} |
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}} |
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'''Diglyme''', or bis(2-methoxyethyl) ether, is a ] with a high ]. It is an ] which is the dimethyl ] of ]. (The name "diglyme" is a ] of "'''digly'''col '''me'''thyl ether.") It is a clear, colorless liquid with a slight ether-like odor. It is miscible with water, ]s, ], and ] solvents. |
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'''Diglyme''', or bis(2-methoxyethyl) ether, is an ] with the ] {{chem2|(CH3OCH2CH2)2O}}. It is a colorless liquid with a slight ether-like odor. It is a ] with a high ]. It is the dimethyl ] of ]. The name ''diglyme'' is a ] of ''diglycol methyl ether''. It is miscible with water as well as organic solvents. |
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It is prepared by a reaction of ] and ] over an acid catalyst.<ref>{{Ullmann | author1 = Siegfried Rebsdat | author2 = Dieter Mayer | title = Ethylene Glycol | doi = 10.1002/14356007.a10_101}}</ref> |
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] ] being chelated by a diglyme molecule]] |
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==Solvent== |
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Diglyme is mainly used as a solvent in organic reactions. It has the ability to ] small ]s, leaving ]s more ]. Therefore, reactions involving ] reagents, such as ]s or metal hydride reductions, may have significantly enhanced reaction rates. |
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<sup>+</sup> as found in its salt with the ] anion.<ref>{{cite journal|title=Novel Fluorenyl Alkali Metal DIGLYME Complexes: Synthesis and Solid State Structures|author=S. Neander |author2=J. Kornich |author3=F. Olbrich |journal=J. Organomet. Chem.|year=2002|volume=656|issue=1–2|page=89|doi=10.1016/S0022-328X(02)01563-2}}</ref>]] |
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Because of its resistance to strong bases, diglyme is favored as a solvent for reactions of alkali metal reagents even at high temperatures. Rate enhancements in reactions involving ] reagents, such as ]s or metal hydride reductions, have been observed when using diglyme as a solvent.<ref>{{cite book |author=J. E. Ellis |author2=A. Davison |author3=G. W. Parshall |author4=E. R. Wonchoba |chapter=TrisPotassium and Tetraphenylarsonium Hexacarbonylmetallates(1–) of Niobium and Tantalum |editor=Fred Basolo |title=Inorganic Syntheses |volume=16 |pages=68–73 |year=1976|doi=10.1002/9780470132470.ch21 |isbn=978-0-470-13247-0}}</ref><ref>{{cite journal |doi=10.15227/orgsyn.053.0052|title=3,5-Dinitrobenzaldehyde|journal=Organic Syntheses|year=1973|volume=53|page=52|author=J. E. Siggins |author2=A. A. Larsen |author3=J. H. Ackerman |author4=C. D. Carabateas}}</ref> |
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Diglyme is also used as a solvent in ] reactions with ].<ref>{{cite journal |doi=10.15227/orgsyn.058.0032|title=Boranes in Functionalization of Olefins to Amines: 3-Pinanamine|journal=Organic Syntheses|year=1978|volume=58|page=32|author=Michael W. Rathke |author2=Alan A. Millard}}</ref><ref>{{cite journal |doi=10.15227/orgsyn.061.0103|title=Perhydro-9b-Boraphenalene and Perhydro-9b-Phenalenol|journal=Organic Syntheses|year=1983|volume=61|page=103|author=Ei-ichi Negishi |author2=Herbert C. Brown}}</ref> |
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Diglyme is also used as a solvent in ] reactions with ]. |
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It serves as a ] for alkali metal ]s, leaving ]s more ]. |
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Its stability, even at high ] values, makes it an excellent solvent for reactions with strong ] or reactions that require high temperatures. |
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==Safety== |
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The ] lists diglyme as a substance of very high concern (SVHC) as a reproductive toxin.<ref>{{Cite web|url=https://www.echa.europa.eu/documents/10162/ee023359-daa8-43a2-8c82-242f0a7588f7|title=Inclusion of Substances of Very High Concern in the Candidate List (Decision of the European Chemicals Agency)|date=19 Dec 2011}}</ref> |
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At higher temperatures and in the presence of active metals diglyme is known to decompose, which can produce large amounts of gas and heat.<ref>{{Cite web|last=Pitt|first=Martin J.|date=July 12, 2010|title=Chemical Safety: Dangers Of Diglyme|url=https://cen.acs.org/articles/88/i28/Chemical-Safety-Dangers-Diglyme.html|url-status=live|access-date=2021-09-01|website=cen.acs.org|archive-url=https://web.archive.org/web/20120511210410/http://cen.acs.org/articles/88/i28/Chemical-Safety-Dangers-Diglyme.html |archive-date=2012-05-11 }}</ref> This decomposition led to the ] in 2007.<ref>{{Cite journal|last1=Willey|first1=Ronald J.|last2=Fogler|first2=H. Scott|last3=Cutlip|first3=Michael B.|date=March 2011|title=The integration of process safety into a chemical reaction engineering course: Kinetic modeling of the T2 incident|url=https://onlinelibrary.wiley.com/doi/10.1002/prs.10431|journal=Process Safety Progress|language=en|volume=30|issue=1|pages=39–44|doi=10.1002/prs.10431|hdl=2027.42/83180|s2cid=109207593|hdl-access=free}}</ref> |
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==References== |
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==References== |
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<references /> |
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*''Merck Index'', 11th Edition, '''3148'''. |
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