Chemistry:Benzamidine
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| Preferred IUPAC name
Benzenecarboximidamide | |
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| Properties | |
| C7H8N2 | |
| Molar mass | 120.155 g·mol−1 |
| Appearance | White solid |
| Density | 1.22 g/cm3 |
| Melting point | 78–80 °C (172–176 °F; 351–353 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
 verify (what is   ?)
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| Infobox references | |
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.[1]
Structure
In terms of its molecular structure, benzamidine features one short C=NH bond and one longer C-NH2 bond, which are respectively 129 and 135 pm in length, respectively.[2]
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.[3]
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.[1]
References
- ↑ 1.0 1.1 Li, Bryan; Chiu, Charles K-F; Hank, Richard F.; Murry, Jerry; Roth, Joshua; Tobiassen, Harry (2005). "Preparation of 2,4-Disubstituted Imidazoles: 4-(4-Methoxyphenyl)-2-Phenyl-1H-Imidazole". Organic Syntheses 81: 105. doi:10.15227/orgsyn.081.0105.
- ↑ Barker, J.; Phillips, P. R.; Wallbridge, M. G. H.; Powell, H. R. (1996). "Benzamidine". Acta Crystallographica Section C Crystal Structure Communications 52 (10): 2617–2619. doi:10.1107/S0108270196006282.
- ↑ Tanizawa, Kazutaka; Ishii, Shin-ichi; Hamaguchi, Kazo; Kanaoka, Yuichi (1971-05-01). "Proteolytic Enzymes. VI. Aromatic Amidines as Competitive Inhibitors of Trypsin". The Journal of Biochemistry 69 (5): 893–899. doi:10.1093/oxfordjournals.jbchem.a129540. ISSN 0021-924X. PMID 5577153. https://www.jstage.jst.go.jp/article/biochemistry1922/69/5/69_5_893/_pdf/-char/en.
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