Tetramethylguanidine is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

with the formula HNC(N(CH)). This colourless liquid is a strong base, as judged by the high pK of its' conjugate acid. It was originally prepared from tetramethyl

thiourea Thiourea () is an organosulfur compound with the formula and the structure . It is structurally similar to urea (), with the oxygen atom replaced by sulfur atom (as implied by the '' thio-'' prefix). The properties of urea and thiourea differ s ...

via ''S''-

methylation Methylation, in the chemistry, chemical sciences, is the addition of a methyl group on a substrate (chemistry), substrate, or the substitution of an atom (or group) by a methyl group. Methylation is a form of alkylation, with a methyl group replac ...

and amination, but alternative methods start from cyanogen iodide.

Uses

Tetramethylguanidine is mainly used as a strong, non-nucleophilic base for

alkylation Alkylation is a chemical reaction that entails transfer of an alkyl group. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effecting al ...

s, 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 Polyurethane (; often abbreviated PUR and PU) is a class of polymers composed of organic chemistry, organic units joined by carbamate (urethane) links. In contrast to other common polymers such as polyethylene and polystyrene, polyurethane term ...

References

{{DEFAULTSORT:Tetramethylguanidine, 1, 1, 3, 3- Guanidines Reagents for organic chemistry Non-nucleophilic bases