Benzamidine

Benzamidine
Names
	IUPAC name Benzenecarboximidamide
Identifiers
CAS Number	618-39-3 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:41033 ;
ChEMBL	ChEMBL20936 ;
ChemSpider	2242 ;
ECHA InfoCard	100.009.589
IUPHAR/BPS	7566;
KEGG	C01784 ;
PubChem CID	2332;
UNII	KUE3ZY3J1F ;
CompTox Dashboard (EPA)	DTXSID8045012 ;
	InChI InChI=1S/C7H8N2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H3,8,9) Key: PXXJHWLDUBFPOL-UHFFFAOYSA-N ; InChI=1/C7H8N2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H3,8,9) Key: PXXJHWLDUBFPOL-UHFFFAOYAU;
	SMILES [NH]=C(N)c1ccccc1;
Properties
Chemical formula	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).
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	Infobox references

Benzamidine is the 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 salt.[1]

In terms of its molecular structure, Benzamidine features one short C=NH bond and one longer C-NH₂ bond, respectively 129 and 135 picometers.[2]

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 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.[1]

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References

Bryan Li, Charles K-F Chiu, Richard F. Hank, Jerry Murry, Joshua Roth, Harry Tobiassen (2005). "Preparation of 2,4-Disubstituted Imidazoles: 4-(4-Methoxyphenyl)-2-Phenyl-1H-Imidazole". Organic Syntheses. 81: 105. doi:10.15227/orgsyn.081.0105.CS1 maint: uses authors parameter (link)
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 EnzymesVI. 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.

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[OS1-1] Bryan Li, Charles K-F Chiu, Richard F. Hank, Jerry Murry, Joshua Roth, Harry Tobiassen (2005). "Preparation of 2,4-Disubstituted Imidazoles: 4-(4-Methoxyphenyl)-2-Phenyl-1H-Imidazole". Organic Syntheses. 81: 105. doi:10.15227/orgsyn.081.0105.CS1 maint: uses authors parameter (link)

[2] 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.

[3] Tanizawa, Kazutaka; Ishii, Shin-ichi; Hamaguchi, Kazo; Kanaoka, Yuichi (1971-05-01). "Proteolytic EnzymesVI. 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.