Benzamidine

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title: "Benzamidine" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["phenyl-compounds", "amidines"] topic_path: "general/phenyl-compounds" source: "https://en.wikipedia.org/wiki/Benzamidine" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Watchedfields = changed | verifiedrevid = 443415204 | ImageFile = Benzamidine.svg | ImageSize = 160px | ImageName = Skeletal formula | ImageFile1 = Benzamidine-3D-balls.png | ImageSize1 = 160px | ImageName1 = Ball-and-stick model | ImageFile2 = BenzamidineHydrochloride.jpg | ImageSize2 = 270px | PIN=Benzenecarboximidamide | OtherNames= |Section1={{Chembox Identifiers | IUPHAR_ligand = 7566 | ChemSpiderID_Ref = | ChemSpiderID = 2242 | KEGG_Ref = | KEGG = C01784 | InChI = 1/C7H8N2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H3,8,9) | InChIKey = PXXJHWLDUBFPOL-UHFFFAOYAU | ChEMBL_Ref = | ChEMBL = 20936 | StdInChI_Ref = | StdInChI = 1S/C7H8N2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H3,8,9) | StdInChIKey_Ref = | StdInChIKey = PXXJHWLDUBFPOL-UHFFFAOYSA-N | CASNo_Ref = | CASNo=618-39-3 | UNII_Ref = | UNII = KUE3ZY3J1F | PubChem=2332 | ChEBI_Ref = | ChEBI = 41033 | SMILES = [NH]=C(N)c1ccccc1 |Section2={{Chembox Properties | C=7 | H=8 | N=2 | Appearance= White solid | Density= 1.22 g/cm3 | MeltingPtC= 64-66 |MeltingPt_ref= | BoilingPt= | Solubility= |Section3={{Chembox Hazards | MainHazards= | FlashPt= | AutoignitionPt =

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|400px]]

References

References

  1. Armarego, W. L. F.. (2003). "Purification of Laboratory Chemicals". Butterworth-Heinemann.
  2. (2005). "Preparation of 2,4-Disubstituted Imidazoles: 4-(4-Methoxyphenyl)-2-Phenyl-1''H''-Imidazole". Organic Syntheses.
  3. (1996). "Benzamidine". Acta Crystallographica Section C Crystal Structure Communications.
  4. Tanizawa, Kazutaka. (1971-05-01). "Proteolytic Enzymes. VI. Aromatic Amidines as Competitive Inhibitors of Trypsin". The Journal of Biochemistry.

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phenyl-compoundsamidines