Benzamidine

Benzamidine
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
Benzenecarboximidamide
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.009.589 Edit this at Wikidata
KEGG
UNII
  • 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
  • [NH]=C(N)c1ccccc1
Properties
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)[1]
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 ?)

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. ^ 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.
  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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