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;
Beilstein Reference	1736101
ChEBI	CHEBI:46784 ;
ChEMBL	ChEMBL1234162;
ChemSpider	13839575 ;
DrugBank	DB02935 ;
ECHA InfoCard	100.003.568
EC Number	203-924-4;
Gmelin Reference	26843
PubChem CID	8150;
RTECS number	KN3339000;
UNII	M4BH3X0MVZ ;
UN number	2252 1993
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	(CH3OCH2CH2)2O
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
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H226, H360
Precautionary statements	P201, P202, P210, P233, P240, P241, P242, P243, P280, P281, P303+P361+P353, P308+P313, P370+P378, P403+P235, P405, P501
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 an organic compound with the chemical formula (CH₃OCH₂CH₂)₂O. It is a colorless liquid with a slight ether-like odor. It is a solvent with a high boiling point. It is the dimethyl ether of diethylene glycol. The name diglyme is a portmanteau of diglycol methyl ether. It is miscible with water as well as organic solvents.

It is prepared by a reaction of dimethyl ether and ethylene oxide over an acid catalyst.^[2]

^ 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.

[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.

[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.

[1]

[2]

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
CAS Number	111-96-6^Y
3D model (JSmol)	Interactive image
Beilstein Reference	1736101
ChEBI	CHEBI:46784^Y
ChEMBL	ChEMBL1234162
ChemSpider	13839575^Y
DrugBank	DB02935^Y
ECHA InfoCard	100.003.568
EC Number	203-924-4
Gmelin Reference	26843
PubChem CID	8150
RTECS number	KN3339000
UNII	M4BH3X0MVZ^Y
UN number	2252 1993
CompTox Dashboard (EPA)	DTXSID1024621
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
SMILES COCCOCCOC
Properties
Chemical formula	(CH₃OCH₂CH₂)₂O
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
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H226, H360
Precautionary statements	P201, P202, P210, P233, P240, P241, P242, P243, P280, P281, P303+P361+P353, P308+P313, P370+P378, P403+P235, P405, P501
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). Y verify (what is ^YN ?) Infobox references

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Diglyme

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