Tetramethylguanidine is an organic compound with the formula HNC(N(CH3)2)2.
This colourless liquid is a strong base, as judged by the high pKa of its' conjugate acid.
[2] It was originally prepared from tetramethylthiourea via S-methylation and amination, but alternative methods start from cyanogen iodide.
[3] Tetramethylguanidine is mainly used as a strong, non-nucleophilic base for alkylations, often as a substitute for the more expensive DBU and DBN.
[3] Since it is highly water-soluble, it is easily removed from mixtures in organic solvents.