3224. 1,2-Dimethoxyethane

Nomenclature

CAS number: 110-71-4
Ethylene glycol dimethyl ether; monoglyme; α,β-dimethoxyethane; glyme; Dimethyl Cellosolve.
C4H10O2; mol wt 90.12.
C 53.31%, H 11.18%, O 35.51%.

Description and references

Prepd from ethylene glycol monomethyl ether, methyl sulfate and metallic sodium: Kranzfelder, Vogt, J. Am. Chem. Soc. 60, 1714 (1938); from ethylene glycol monomethyl ether, methyl chloride and sodium: Capinjola, ibid. 67, 1615 (1945); from chloromethyl methyl ether in the presence of sodium by Wurtz reaction: Geist, Mason, ibid. 76, 3728 (1954). Series of articles on toxicology: Environ. Health Perspect. 57, 1-275 (1984).

Chemical structure

Properties

Liquid. Sharp ethereal odor. d415 0.86877; d420 0.86285; d433 0.8602; d2020 0.8692. mp -58° (also reported as mp -71°). bp760 82-83°; bp61.2 20°; bp50 16°; bp10 -14°. nD24 1.3739; nD20 1.3813. Flash pt 4.5°C (40°F). Miscible with water, alcohol. Sol in hydrocarbon solvents.

Use

Solvent, to facilitate the formation of alkali metal-hydrocarbon adducts; in the Reformatsky reaction with methyl γ-bromocrotonate.