Diglyme
 | |
 | |
| Names | |
|---|---|
| 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) |
|
| ChEBI | |
| ChemSpider | |
| DrugBank | |
| ECHA InfoCard | 100.003.568 |
| EC Number | 203-924-4 |
| PubChem CID |
|
| UNII | |
| |
| |
| Properties | |
| C6H14O3 | |
| Molar mass | 134.18 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 | |
| EU classification (DSD) (outdated) |
Toxic (T) Flammable (F) |
| R-phrases (outdated) | R60 R61 R10 R19 |
| S-phrases (outdated) | S53 S45 |
| Flash point | 57 °C (135 °F; 330 K) |
| Related compounds | |
| Related compounds |
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). | |
 verify (what is  ?) | |
| Infobox references | |
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 clear, colorless liquid with a slight ether-like odor. It is miscible with water, alcohols, diethyl ether, and hydrocarbon solvents. It is prepared by a reaction of dimethyl ether and ethylene oxide over a acid catalyst.[2]
Solvent
Its stability, even at high pH values, makes it an excellent solvent for reactions with strong bases or reactions that require high temperatures.
Diglyme is mainly used as a solvent in organic reactions. It has the ability to chelate small cations, leaving anions more active. Therefore, reactions involving organometallic reagents, such as Grignard reactions or metal hydride reductions, may have significantly enhanced reaction rates. Diglyme is also used as a solvent in hydroboration reactions with diborane.
References
- ↑ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 704. ISBN 978-0-85404-182-4. doi:10.1039/9781849733069-FP001.
- ↑ Siegfried Rebsdat; Dieter Mayer (2005), "Ethylene Glycol", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a10_101