tert-Butoxybis(dimethylamino)methane is an organic compound with the formula (CH3)3COCH(N(CH3)2)2. The compound is classified as an aminal ester, i.e. the tert-butyl alcohol derivative of the aminal bis(dimethylamino)methane. It is a colorless liquid with a amine odor.
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]