Benzamidine

Benzamidine

Skeletal formula Skeletal formula
Ball-and-stick model Ball-and-stick model
File:BenzamidineHydrochloride.jpg
Names
Preferred IUPAC name Benzenecarboximidamide
Identifiers
CAS Number	618-39-3 checkY
3D model (JSmol)	Interactive image
ChEBI	CHEBI:41033 checkY
ChEMBL	ChEMBL20936 checkY
ChemSpider	2242 checkY
ECHA InfoCard
E number
IUPHAR/BPS	7566
KEGG	C01784 checkY
PubChem CID	2332
UNII	KUE3ZY3J1F checkY
CompTox Dashboard (EPA)	{{#property:P3117}}
InChI InChI=1S/C7H8N2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H3,8,9) checkY Key: PXXJHWLDUBFPOL-UHFFFAOYSA-N checkY 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). checkY verify (what is checkY☒N ?) 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.

Structure

Benzamidine has one short C=NH bond and one longer C-NH₂ bond, which are respectively 129 and 135 pm in length, respectively.

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.

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.

File:Disubstituted-imidazole-synthesis OrgSyn.png