Benzamidine

Benzamidine

Names
Preferred IUPAC name Benzenecarboximidamide
Identifiers
CAS Number	618-39-3^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:41033^Y
ChEMBL	ChEMBL20936^Y
ChemSpider	2242^Y
ECHA InfoCard	100.009.589
IUPHAR/BPS	7566
KEGG	C01784^Y
PubChem CID	2332
UNII	KUE3ZY3J1F^Y
CompTox Dashboard (EPA)	DTXSID8045012
InChI InChI=1S/C7H8N2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H3,8,9)^Y Key: PXXJHWLDUBFPOL-UHFFFAOYSA-N^Y 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/cm^3
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). Y verify (what is ^YN ?) 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.^[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]

References

1. Armarego, W. L. F.; Chai, Christina Li Lin (2003). Purification of Laboratory Chemicals. Amsterdam ; Boston: Butterworth-Heinemann. p. 119. ISBN 978-0-7506-7571-0. OCLC 52733960.
2. 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.
3. 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.
4. 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.