Tris(dimethylamino)methane

Tris(dimethylamino)methane is formed in the reaction of N,N,N′,N′-Tetramethylformamidinium chloride (TMF-Cl) or bis(dimethylamino)acetonitrile with lithium dimethylamide or sodium dimethylamide with yields between 55 and 84%. : The reaction of the dimethylformamide (DMF) dimethylacetal, HC(OCH3)2N(CH3)2, (from the DMF–dimethyl sulfatecomplex and sodium methoxide) with dimethylamine in the presence of the acidic catalyst 2,4,6-tri-tert-butylphenol (which is largely stable to the alkylating agent) produces tris(dimethylamino)methane. : Tris(dimethylamino)methane is formed in good yield (83%) in the reaction of DMF with tetrakis(dimethylamino)titanium(IV). : N,N,N,N,N″,N″-Hexamethylguanidinium chloride (readily obtainable by dimethylamine and N,N,N,N-tetramethylchloroformamidinium chloride derived from tetramethylurea and phosgene) forms tris(dimethylamino)methane in 53% yield under the exposure of the reducing agent sodium bis(2-methoxyethoxy)aluminium hydride (Red-Al). Sodium hydride and trimethyl borate reduce N,N,N,N,N″,N″-hexamethylguanidinium chloride in 80% yield to tris(dimethylamino)methane. : == Properties ==

Tris(dimethylamino)methane is a clear, colorless or pale yellow liquid with a strong ammoniacal odor. The compound is freely miscible with many non-polar aprotic and water-free solvents. However, when heated tris(dimethylamino)methane reacts with protic solvents (such as water or alcohols) but also with weak CH-acidic substances, such as acetone or acetonitrile. a strong electron donor. : == Applications ==

Tris(dimethylamino)methane dissociates into N,N,N,N-tetramethylformamidinium cations and dimethylamide anions, which abstract protons from CH- and NH-acidic compounds. The anions thus formed add to the formamidinium cations which in turn eliminate dimethylamine and react to form dimethylaminomethylene compounds (= CH−N(CH3)2) or amidines by aminomethyleneation. : ==Related reagent==

• Bis(dimethylamino)methane == References ==