Tetramethylguanidine

Chemical properties

N,N,N',N' -Tetramethylguanidine (TMG) [80-70-6], C5H13N3, Mr 115.18, is a stable, unusually strong base, pKa 13.6 (25 ℃), with a free imino group. It is a colorless to light-yellow liquid, miscible with water and common organic solvents: 0.92 g/cm3 (25 ℃), bp 160 ℃, vapor pressure 0.03 kPa (25℃).

The Uses of Tetramethylguanidine

Base employed in the preparation of alkyl nitriles from alkyl halides and 3′-alkylthymidines from 3′-nitrothymidines.

The Uses of Tetramethylguanidine

1,1,3,3-Tetaramethylguanidine is used as a strong, non-nucleophilic base for alkylations in organic synthesis. 1,1,3,3-Tetramethylguanidine is an efficient and selective catalyst for the benzoylation of alcohols.

The Uses of Tetramethylguanidine

Tetramethylguanidine (TMG) is used as polyurethane foam catalyst, as accelerator for the syntheses of polysulfured rubber, as a strong base in the photochemical (e.g. couplers) and in the pharmaceutical (e.g. steroids) industries. Product Data Sheet

Flammability and Explosibility

Flammable

Synthesis

Prepared from cyanogen chloride and dimethylamine in a 1 : 2 molar ratio, TMG is used as a polyurethane foam catalyst, in the preparation of pigments for color photography, and in steroid synthesis. 

Purification Methods

Reflux it over granulated BaO, then fractionally distil it. Protect it from CO2. [Beilstein 4 IV 227.]