Tetramethylguanidine is an organic compound with the formula HNC(N(CH)). This colourless liquid, while technically a "weak base," is a relatively strong base, as judged by the high pK of its conjugate acid.
It was originally prepared from tetramethylthiourea via S-methylation and amination, but alternative methods start from cyanogen iodide.
Uses Tetramethylguanidine is mainly used as a strong, non-nucleophilic base for alkylations, often as a substitute for the more expensive DBU and DBN. Since it is highly water-soluble, it is easily removed from mixtures in organic solvents. It is also used as a base-catalyst in the production of polyurethane.
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