Diglyme

Diglyme
Names
	Preferred IUPAC name 1-Methoxy-2-(2-methoxyethoxy)ethane
	Other names Diglyme; 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. It is prepared by a reaction of dimethyl ether and ethylene oxide over an 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. It serves as a chelate for alkali metal cations, leaving anions more active. Therefore, reactions involving organometallic reagents, such as Grignard reactions or metal hydride reductions, may have significantly enhanced reaction rates.^[3] 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. 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.
^ "Tris[Bis(2-Methoxyethyl)Ether]Potassium and Tetraphenylarsonium Hexacarbonylmetallates(1–) of Niobium and Tantalum". Inorg. Synth. 16: 68–73. 1976. doi:10.1002/9780470132470.ch21. {{cite journal}}: Cite uses deprecated parameter |authors= (help)

[iupac2013-1] 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.

[Ullmanns-2] Siegfried Rebsdat; Dieter Mayer. "Ethylene Glycol". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_101. ISBN 978-3527306732.

[3] "Tris[Bis(2-Methoxyethyl)Ether]Potassium and Tetraphenylarsonium Hexacarbonylmetallates(1–) of Niobium and Tantalum". Inorg. Synth. 16: 68–73. 1976. doi:10.1002/9780470132470.ch21. {{cite journal}}: Cite uses deprecated parameter |authors= (help)

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