618-39-3

Basic information

• Product Name: BENZAMIDINE
• Synonyms: BENZAMIDINE;BENZENECARBOXIMIDAMIDE;phenylamidine;EINECS 210-546-3;benzenecarbonamidine;benzylamidine;Phenylmethanamidine;α-Iminobenzenemethanamine
• CAS NO: 618-39-3
• Molecular Formula: C₇H₈N₂
• Molecular Weight: 120.15
• EINECS: 210-546-3
• Product Categories: pharmacetical;Imines/Amidines;Nitrogen Compounds;Organic Building Blocks;B;Bioactive Small Molecules;Building Blocks;Cell Biology;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks
• Mol File: 618-39-3.mol
• Article Data: 33

Chemical Properties

• Melting Point: 65-70 °C
• Boiling Point: 208.5 °C at 760 mmHg
• Flash Point: 79.9 °C
• Appearance: /
• Density: 1.09 g/cm³
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 11.90±0.40(Predicted)
• BRN: 606020
• CAS DataBase Reference: BENZAMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZAMIDINE(618-39-3)
• EPA Substance Registry System: BENZAMIDINE(618-39-3)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 26
• WGK Germany: 3
• F: 9-23
• Hazardous Substances Data: 618-39-3(Hazardous Substances Data)

Usage

Chemical Description

Benzamidine is a molecule with biological and pharmacological relevance.

Uses

Benzamidine was used in the preparation of heparan sulfate-rich proteoglycan from mouse mammary epithelial cells. It has been used to prevent enzymatic degradation during the purification procedure of bovine factor XII (Hageman factor).

Synthesis Reference(s)

The Journal of Organic Chemistry, 27, p. 1255, 1962 DOI: 10.1021/jo01051a033Tetrahedron Letters, 31, p. 1969, 1990 DOI: 10.1016/S0040-4039(00)88891-7

Biochem/physiol Actions

Benzamidine is an inhibitor of plasmin and has been used in the radioimmunoassay of glucagon in human plasma. It prevents the destruction of Thyrotropin-releasing hormone (TRH) added to whole blood in vitro before radioimmunoassay of TRH.

Purification Methods

It is liberated from its hydrochloride chloride (below) by treatment with 5M NaOH, extracted into diethyl ether, dried (Na2SO4) and sublimed in vacuo.[Beilstein 9 H 280, 9 I 123, 9 II 199, 9 1264, 9 IV 898.]

InChI:InChI=1/C7H8N2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H3,8,9)

Upstream product

• 1147550-11-5 ammonium thiocyanate 
• 100-47-0 benzonitrile 
• 930-69-8 sodium thiophenolate 
• 4460-46-2 3-chloro-3-phenyl-3H-diazirine 
• 4222-25-7 3-bromo-3-phenyl-3H-diazirine 
• 7446-70-0 aluminium trichloride 
• 7664-41-7 ammonia 
• 108-88-3 toluene 
• 7647-01-0 hydrogenchloride 
• 613-92-3 N-hydroxybenzenecarboximidamide 
• 100-66-3 methoxybenzene 
• 64-17-5 ethanol 
• 40078-03-3 N-chloro-benzamidine 
• 7732-18-5 water 

Downstream Products

• 1722-18-5 2-phenyl-1,3,5-triazine 
• 1898-74-4 2,4-diphenyl-1,3,5-triazine 
• 22454-72-4 N-ethoxycarbonylbenzamidine 
• 3599-62-0 2-methyl-4,6-diphenyl-1,3,5-triazine 
• 67280-51-7 N-(2,2,2-trichloro-1-hydroxy-ethyl)-benzamidine 
• 79566-38-4 N-methylthiocarbamoyl-benzamidine 
• 1917-44-8 4,6-diphenyl-1H-[1,3,5]triazin-2-one 
• 26196-28-1 N-benzylidene-benzamidine 
• 46180-43-2 2-phenyl-1H-imidazole-4,5-dione 
• 16776-73-1 N-benzoyl-benzamidine 
• 17513-09-6 N-cyanobenzamidine 
• 34771-48-7 4-methyl-2-phenylpyrimidine 
• 27058-47-5 Ethyl 3 benzamidino-2 cyanoacrylate 
• 27058-46-4 4-amino-2-phenyl-pyrimidine-5-carboxylic acid ethyl ester 

Relevant articles and documents

Benzamidine

Benzenecarboximidamide, C7H8N2, has been prepared and its structure shows a planar molecule with distinct C double bond N 1.294 (3) and C - N 1.344 (3) angstroms distances, and a three-dimensional hydrogen-bonding network.

Assembly of 5-Aminoimidazoles via Palladium-Catalysed Double Isocyanide Insertion Reaction

A palladium-catalysed tandem cyclisation reaction of amidoximes, isocyanides and amines to produce 5-aminoimidazoles was developed. Various 5-aminoimidazoles were prepared in good to excellent yields under mild conditions. This elegant domino process involves the effective cleavage of the N?O bond and the formation of new C?C and C?N bonds in a single operation. (Figure presented.).

Novel Allosteric Inhibitors of Deoxyhypusine Synthase against Malignant Melanoma: Design, Synthesis, and Biological Evaluation

Based on the novel allosteric site of deoxyhypusine synthase (DHPS), two series of 30 novel 5-(2-methoxyphenoxy)-2-phenylpyrimidin-4-amine derivatives as DHPS inhibitors were designed and synthesized. Among them, compound8m, with the best DHPS inhibitory potency (IC50= 0.014 μM), exhibited excellent inhibition against melanoma cells, which was superior to that of GC7. Besides, molecular docking and molecular dynamics (MD) simulations further proved that compound8mwas tightly bound to the allosteric site of DHPS. Flow cytometric analysis and enzyme-linked immunosorbent assay (ELISA) showed that compound8mcould inhibit the intracellular reactive oxygen species (ROS) level. Furthermore, by western blot analysis, compound8meffectively activated caspase 3 and decreased the expressions of GP-100, tyrosinase, eIF5A2, MMP2, and MMP9. Moreover, both Transwell analysis and wound healing analysis showed that compound8mcould inhibit the invasion and migration of melanoma cells. In thein vivostudy, the tumor xenograft model showed that compound8meffectively inhibited melanoma development with low toxicity.

Sulfated tungstate catalyzed activation of nitriles: addition of amines to nitriles for synthesis of amidines

An efficient and mild method for the synthesis of amidines by direct nucleophilic addition of amines to nitriles using sulfated tungstate as heterogeneous catalyst is described. Highlight of the method is its applicability for the synthesis of amidines using a wide variety of amines including ammonia as ammonium acetate and nitriles. Catalyst is mildly acidic, stable, easy to prepare and separate from the reaction mass.