Benzamidine
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Names | |
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Preferred IUPAC name
Benzenecarboximidamide | |
Identifiers | |
3D model (JSmol)
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ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.009.589 |
KEGG | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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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).
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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]
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]
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