Tris(dimethylamino)methane
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Tris(dimethylamino)methane
Tris(dimethylamino)methane (TDAM) is the simplest representative of the tris(dialkylamino)methanes of the general formula (R2N)3CH in which three of the four of methane's hydrogen atoms are replaced by dimethylamino groups (−N(CH3)2). Tris(dimethylamino)methane can be regarded as both an amine and an orthoamide. Tris(dimethylamino)methane is a strong base and can be used as a Formylation, formylation agent, as Aminomethylenation, aminomethylenation reagent and as a source for the basic bis(dimethylamino)carbene of the formula (R2N)2C:. Preparation 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%. :: From dimethylamine and trimethoxyborane sodium dimethylamide is formed ''in situ'' in the presence of sodium hydride which reacts with ''N'',''N'',''N'',''N''-tetramethylformamidinium chloride in 84% yi ...
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Amine
In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group (these may respectively be called alkylamines and arylamines; amines in which both types of substituent are attached to one nitrogen atom may be called alkylarylamines). Important amines include amino acids, biogenic amines, trimethylamine, and aniline; Inorganic derivatives of ammonia are also called amines, such as monochloramine (). The substituent is called an amino group. Compounds with a nitrogen atom attached to a carbonyl group, thus having the structure , are called amides and have different chemical properties from amines. Classification of amines Amines can be classified according to the nature and number of substituents on nitrogen. Aliphatic amines contain only H and alkyl substituents. A ...
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