Diglyme

Diglyme
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
CAS Number	111-96-6 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:46784 ;
ChemSpider	13839575 ;
DrugBank	DB02935 ;
ECHA InfoCard	100.003.568
EC Number	203-924-4;
PubChem CID	8150;
UNII	M4BH3X0MVZ ;
CompTox Dashboard (EPA)	DTXSID1024621 ;
	InChI InChI=1S/C6H14O3/c1-7-3-5-9-6-4-8-2/h3-6H2,1-2H3 Key: SBZXBUIDTXKZTM-UHFFFAOYSA-N ; InChI=1/C6H14O3/c1-7-3-5-9-6-4-8-2/h3-6H2,1-2H3 Key: SBZXBUIDTXKZTM-UHFFFAOYAG;
	SMILES COCCOCCOC;
Properties
Chemical formula	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)
Solubility in water	miscible
Hazards
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.

A lithium cation being chelated by a diglyme molecule

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.