Diglyme

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Diglyme

Preferred IUPAC name Diglyme
Systematic 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^Y
PubChem	8150
ChemSpider	13839575^Y
UNII	M4BH3X0MVZ^Y
EC number	203-924-4
DrugBank	DB02935
ChEBI	CHEBI:46784^Y
Jmol-3D images	Image 1
SMILES COCCOCCOC
InChI InChI=1S/C6H14O3/c1-7-3-5-9-6-4-8-2/h3-6H2,1-2H3^Y Key: SBZXBUIDTXKZTM-UHFFFAOYSA-N^Y InChI=1/C6H14O3/c1-7-3-5-9-6-4-8-2/h3-6H2,1-2H3 Key: SBZXBUIDTXKZTM-UHFFFAOYAG
Properties
Molecular formula	C₆H₁₄O₃
Molar mass	134.17 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
EU classification	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
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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.

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