Diglyme
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| Names | |
|---|---|
| Preferred IUPAC name
Diglyme | |
| Systematic IUPAC name
1-Methoxy-2-(2-methoxyethoxy)ethane | |
| Other names
2-Methoxyethyl ether; Di(2-methoxyethyl) ether; Diethylene glycol dimethyl ether | |
| Identifiers | |
111-96-6  | |
| 3D model (Jmol) | Interactive image |
| ChEBI | CHEBI:46784 |
| ChemSpider | 13839575 |
| DrugBank | DB02935 |
| ECHA InfoCard | 100.003.568 |
| EC Number | 203-924-4 |
| PubChem | 8150 |
| UNII | M4BH3X0MVZ |
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| 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) |
Toxic (T) Flammable (F) |
| R-phrases | R60 R61 R10 R19 |
| S-phrases | 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). | |
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| 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.
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.
Its stability, even at high pH values, makes it an excellent solvent for reactions with strong bases or reactions that require high temperatures.
References
- Merck Index, 11th Edition, 3148.