tert-Butoxybis(dimethylamino)methane

tert-Butoxybis(dimethylamino)methane is an organic compound with the formula (CH3)3COCH(N(CH3)2)2.

Also known as Bredereck's reagent, it is used for formylation (introduction of the CHO group).

[1] Protonation releases tert-butyl alcohol, giving tetramethylformamidinium, which displaces active C-H bonds: The resulting bis(dimethylamino)methyl derivative in turn releases dimethylamine to give an enamine, which hydrolyzes.

Tert-Butoxybis(dimethylamino)methane is obtained from tetramethylformamidinium chloride by reaction with tert-butoxide.

Tetramethylformamidinium salts are obtained by the reaction of dimethylformamide (DMF) with dimethylcarbamoyl chloride[2]