Benzamidine
Benzamidine is the organic compound with the formula C6H5CNH2. It is the simplest aryl amidine. The compound is a white solid that is slightly soluble in water. It is usually handled as the hydrochloride salt, a white, water-soluble salt.
In terms of its molecular structure, Benzamidine features one short C=NH bond and one longer C-NH2 bond, respectively 129 and 135 picometers.Applications
Benzamidine is a reversible competitive inhibitor of trypsin, trypsin-like enzymes and serine proteases.
It is often used as a ligand in protein crystallography to prevent proteases from degrading a protein of interest; the triangular diamine group at the bottom gives it a very obvious 'stick-man' shape which shows up in difference density maps. The benzamidine moiety is also found in some pharmaceuticals, like dabigatran.
Condensation with α-haloketones provides the imidazole.
