Tris(dimethylamino)methane

[6] The reaction of the dimethylformamide (DMF) dimethylacetal, HC(OCH3)2N(CH3)2, (from the DMF–dimethyl sulfate complex and sodium methoxide[7]) 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.

[6] Tris(dimethylamino)methane is a clear, colorless or pale yellow liquid with a strong ammoniacal odor.

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.

[2] Upon heating to 150–190 °C decomposition occurs with the formation of tetrakis(dimethylamino)ethene,[12] a strong electron donor.

[13] Tris(dimethylamino)methane dissociates into N,N,N′,N′-tetramethylformamidinium cations and dimethylamide anions, which abstract protons from CH- and NH-acidic compounds.

Synthesis of TDAM from TMF-Cl and lithium dimethylamide
Synthesis of TDAM from TMF-Cl and lithium dimethylamide
Synthesis of TDAM from TMF-Cl and sodium dimethylamide with trimethoxyborane
Synthesis of TDAM from TMF-Cl and sodium dimethylamide with trimethoxyborane
Synthesis of TDAM from the dimethylacetal of DMF
Synthesis of TDAM from the dimethylacetal of DMF
Synthesis of TDAM from DMF with tetrakis(dimethylamino)titanium(IV)
Synthesis of TDAM from DMF with tetrakis(dimethylamino)titanium(IV)
Synthesis of TDAM from hexamethylguanidinium chloride
Synthesis of TDAM from hexamethylguanidinium chloride
Synthesis of tetrakis(dimethylamino)ethene
Synthesis of tetrakis(dimethylamino)ethene
Synthesis of methyl α-cyano-β-dimethylaminoacrylate
Synthesis of methyl α-cyano-β-dimethylaminoacrylate
N,N-Dimethyl-N′-p-nitrophenylformamidine synthesis with TDAM
N , N -Dimethyl- N ′ - p -nitrophenylformamidine synthesis with TDAM
Synthesis of tetramethylselenourea with TDAM
Synthesis of tetramethylselenourea with TDAM