Diglyme

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 colorless liquid with a slight ether-like odor. It is miscible with water as well as organic solvents.

Diglyme
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
3D model (JSmol)
ChEBI
ChemSpider
DrugBank
ECHA InfoCard 100.003.568
EC Number
  • 203-924-4
UNII
Properties
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)
miscible
Hazards
Toxic (T)
Flammable (F)
R-phrases (outdated) R60 R61 R10 R19
S-phrases (outdated) S53 S45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

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

Solvent
Structure of [Na(diglyme)2]+ as found in its salt with the fluorenyl anion.[3]

Because of its resiliance to strong bases, diglyme is favored as a solvent for reactions of alkali metal reagents even at high temperatures. Therefore, reactions involving organometallic reagents, such as Grignard reactions or metal hydride reductions, may have significantly enhanced reaction rates.[4][5]

Diglyme is also used as a solvent in hydroboration reactions with diborane.[6][7]

It serves as a chelate for alkali metal cations, leaving anions more active.

Safety

The European Chemicals Agency lists diglyme as a Substances of Very High Concern (SVHC) as a Reproductive Toxin.[8]


References
  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.
  3. S. Neander, J. Kornich, F. Olbrich (2002). "Novel Fluorenyl Alkali Metal DIGLYME Complexes: Synthesis and Solid State Structures". J. Organomet. Chem. 656 (1–2): 89. doi:10.1016/S0022-328X(02)01563-2.CS1 maint: uses authors parameter (link)
  4. J. E. Ellis, A. Davison (1976). "Tris[Bis(2-Methoxyethyl)Ether]Potassium and Tetraphenylarsonium Hexacarbonylmetallates(1-) of Niobium and Tantalum". Tris[Bis(2-Methoxyethyl)Ether]Potassium and Tetraphenylarsonium Hexacarbonylmetallates(1–) of Niobium and Tantalum. Inorg. Synth. Inorganic Syntheses. 16. pp. 68–73. doi:10.1002/9780470132470.ch21. ISBN 9780470132470.CS1 maint: uses authors parameter (link)
  5. J. E. Siggins, A. A. Larsen, J. H. Ackerman, C. D. Carabateasr=J. E. Siggins, A. A. Larsen, J. H. Ackerman, and C. D. Carabateas (1973). "3,5-Dinitrobenzaldehyde". Organic Syntheses. 53: 52. doi:10.15227/orgsyn.053.0052.CS1 maint: uses authors parameter (link)
  6. Michael W. Rathke, Alan A. Millard (1978). "Boranes in Functionalization of Olefins to Amines: 3-Pinanamine". Organic Syntheses. 58: 32. doi:10.15227/orgsyn.058.0032.CS1 maint: uses authors parameter (link)
  7. Ei-ichi Negishi, Herbert C. Brown (1983). "Perhydro-9b-Boraphenalene and Perhydro-9b-Phenalenol". Organic Syntheses. 61: 103. doi:10.15227/orgsyn.061.0103.CS1 maint: uses authors parameter (link)
  8. "Inclusion of Substances of Very High Concern in the Candidate List (Decision of the European Chemicals Agency)". 19 Dec 2011.
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