Benzamidine

Benzamidine
Names
	Preferred 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	64–66 °C (147–151 °F; 337–339 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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

^ 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.
^ ^a ^b 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.

[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.

[OS1-2] 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.

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