Tetramethoxymethane

Description

Tetramethoxymethane can be usede in ?CO2 fixation, formation of orthocarbonates from diols and electrophilic introduction of an ester functionality.

Uses

Tetramethoxymethane has application within an electrolyte solution for the use of rechargeable lithium batteries. It has also been used as a reactant in the synthesis of novel anti-HIV-1 compounds.

Synthesis

Tetramethoxymethane has been prepared by heating a solution of Sodium Methoxide in methanol with chloropicrin, Trichloroacetonitrile, or thiocarbonyl perchlorate; the best yields have been obtained with the perchlorate. Alternatively, disodium hexamethoxystannate (prepared in situ from sodium methoxide and tetrachlorostannane) can be refluxed with Carbon Disulfide in methanol to form the orthocarbonate.

Purification Methods

Tetramethyl orthocarbonate (methyl orthocarbonate, tetramethoxy methane) [1850-14-2] M 136.2, m -5.6o, -5o, -2o, b 113.5o/760mm, 113.5 -114o/755mm, 112-114o/atm, d 4 1.0202, n D 1.3860. Purify it in the same way as for tetraethyl orthocarbonate. [Smith Acta Chem Scand 10 1006 1956, Tiekelmann & Post J Org Chem 13 266 1948, Kantlehner et al. Synthesis 73 1977, Beilstein 3 IV 4.]