Diglyme
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| Names | |
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| Preferred IUPAC name
1-Methoxy-2-(2-methoxyethoxy)ethane[1] | |
| Other names
Diglyme
2-Methoxyethyl ether Di(2-methoxyethyl) ether Diethylene glycol dimethyl ether | |
| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
| DrugBank | |
| ECHA InfoCard | 100.003.568 |
| EC Number |
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PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C6H14O3 | |
| Molar mass | 134.175 g·mol−1 |
| Density | 0.937 g/mL |
| Melting point | −64 °C (−83 °F; 209 K) |
| Boiling point | 162 °C (324 °F; 435 K) |
| miscible | |
| Hazards | |
| Flash point | 57 °C (135 °F; 330 K) |
| Related compounds | |
Related compounds
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Diethylene glycol diethyl ether, ethylene glycol dimethyl ether |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Diglyme, or bis(2-methoxyethyl) ether, is a solvent with a high boiling point. It is an organic compound which is the dimethyl ether of diethylene glycol. (The name "diglyme" is a portmanteau of "diglycol methyl ether.") It is a colorless liquid with a slight ether-like odor. It is miscible with water as well as organic solvents.
It is prepared by a reaction of dimethyl ether and ethylene oxide over an acid catalyst.[2]
Solvent
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Because of its resiliance to strong bases, diglyme is favored as a solvent for reactions of alkali metal reagents even at high temperatures. Therefore, reactions involving organometallic reagents, such as Grignard reactions or metal hydride reductions, may have significantly enhanced reaction rates.[4][5]
Diglyme is also used as a solvent in hydroboration reactions with diborane.[6][7]
It serves as a chelate for alkali metal cations, leaving anions more active.
Safety
The European Chemicals Agency lists diglyme as a Substances of Very High Concern (SVHC) as a Reproductive Toxin.[8]
References
- ^ 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-FP001. ISBN 978-0-85404-182-4.
- ^ Siegfried Rebsdat; Dieter Mayer. "Ethylene Glycol". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_101. ISBN 978-3527306732.
- ^ "Novel Fluorenyl Alkali Metal DIGLYME Complexes: Synthesis and Solid State Structures". J. Organomet. Chem. 656 (1–2): 89. 2002. doi:10.1016/S0022-328X(02)01563-2.
{{cite journal}}: Cite uses deprecated parameter|authors=(help) - ^ Tris[Bis(2-Methoxyethyl)Ether]Potassium and Tetraphenylarsonium Hexacarbonylmetallates(1–) of Niobium and Tantalum. Inorganic Syntheses. Vol. 16. 1976. pp. 68–73. doi:10.1002/9780470132470.ch21. ISBN 9780470132470.
{{cite book}}:|journal=ignored (help); Cite uses deprecated parameter|authors=(help) - ^ "3,5-Dinitrobenzaldehyde". Organic Syntheses. 53: 52. 1973. doi:10.15227/orgsyn.053.0052.
{{cite journal}}: Cite uses deprecated parameter|authors=(help) - ^ "Boranes in Functionalization of Olefins to Amines: 3-Pinanamine". Organic Syntheses. 58: 32. 1978. doi:10.15227/orgsyn.058.0032.
{{cite journal}}: Cite uses deprecated parameter|authors=(help) - ^ "Perhydro-9b-Boraphenalene and Perhydro-9b-Phenalenol". Organic Syntheses. 61: 103. 1983. doi:10.15227/orgsyn.061.0103.
{{cite journal}}: Cite uses deprecated parameter|authors=(help) - ^ "Inclusion of Substances of Very High Concern in the Candidate List (Decision of the European Chemicals Agency)". 19 Dec 2011.