Benzamidine
Chemical compound
From Wikipedia, the free encyclopedia
Benzamidine is an organic compound with the formula C6H5C(NH)NH2. 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 solid.[2]
 | |
 | |
 | |
| Names | |
|---|---|
| Preferred IUPAC name
Benzenecarboximidamide | |
| Identifiers | |
3D model (JSmol) |
|
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.009.589 |
| KEGG | |
PubChem CID |
|
| UNII | |
CompTox Dashboard (EPA) |
|
| |
| |
| Properties | |
| C7H8N2 | |
| Molar mass | 120.155 g·mol−1 |
| Appearance | White solid |
| Density | 1.22 g/cm3 |
| Melting point | 64–66 °C (147–151 °F; 337–339 K)[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
Structure
Benzamidine has one short C=NH bond and one longer C-NH2 bond, which are respectively 129 and 135 pm in length, respectively.[3]
The triangular diamine group gives it a distinctive shape which shows up in difference density maps.
Applications
Benzamidine is a reversible competitive inhibitor of trypsin, trypsin-like enzymes, and serine proteases.[4]
It is often used as a ligand in protein crystallography to prevent proteases from degrading a protein of interest. The benzamidine moiety is also found in some pharmaceuticals, such as dabigatran.
Condensation with various haloketones provides a synthetic route to 2,4-disubstituted imidazoles.[2]
