Cyanoguanidines

Cyanoguanidines are a class of nitrogen-rich organic compounds that derive from the guanidine framework and feature one or more cyano substituents. The guanidine core contributes high basicity and the ability to form multiple hydrogen bonds, while cyano groups bring additional electronic effects and reactivity, enabling diverse transformations. The term encompasses a family of related compounds rather than a single defined structure, with variations in substitution patterns on the guanidine nitrogen atoms or at the central carbon.

In general, cyanoguanidines are prepared by introducing cyano functionality into guanidine or its derivatives, using cyanating agents or condensation reactions. Depending on the method and substrates, a range of monosubstituted or polysubstituted cyanoguanidines can be obtained. Their stability, solubility, and salt-forming properties can vary with substitution and counterions.

Applications of cyanoguanidines lie primarily in organic synthesis and materials chemistry. They serve as intermediates for the preparation of substituted amidines and heterocycles, and some derivatives are used as building blocks in pharmaceutical and agrochemical research. They can also act as ligands or precursors in polymerization processes, where their multiple nitrogen sites enable coordination or crosslinking.

Safety and handling considerations are important when working with cyanoguanidines. They are generally handled as solids or solutions under standard laboratory conditions, with attention to irritant properties and potential toxicity. Cyanoguanidines should be stored away from strong oxidizers and acids, and appropriate personal protective equipment should be used in the laboratory. Further information is found in product-specific safety data sheets.