5418-95-1

Basic information

• Product Name: 2-GUANIDINOBENZIMIDAZOLE
• Synonyms: AKOS BC-1905;2-GUANIDINOBENZIMIDAZOLE;OTAVA-BB BB0111070250;TOSLAB-BB TOS-BB-1283;TIMTEC-BB SBB003790;1h-benzimidazol-2-yl-guanidin;1-(benzimidazol-2-yl)guanidine;2-GUANIDINOBENZIMIDAZOLE 95%
• CAS NO: 5418-95-1
• Molecular Formula: C₈H₉N₅
• Molecular Weight: 175.19
• EINECS: 226-527-8
• Product Categories: BENZIMIDAZOLE;Benzimidazoles;Building Blocks;Heterocyclic Building Blocks;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 5418-95-1.mol
• Article Data: 12

Chemical Properties

• Melting Point: 242-244 °C (dec.)(lit.)
• Boiling Point: 296.48°C (rough estimate)
• Flash Point: 233 °C
• Appearance: /
• Density: 1.2954 (rough estimate)
• Vapor Pressure: 1.05E-08mmHg at 25°C
• Refractive Index: 1.6900 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Soluble in DMSO (up to 50 mg/ml) or in Water (up to 4 mg/ml with warming)
• PKA: 13.67±0.30(Predicted)
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20°C for up to 3 months.
• CAS DataBase Reference: 2-GUANIDINOBENZIMIDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-GUANIDINOBENZIMIDAZOLE(5418-95-1)
• EPA Substance Registry System: 2-GUANIDINOBENZIMIDAZOLE(5418-95-1)

Safety Data

• Safety Statements: S24/25:Avoid contact with skin and eyes.
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 5418-95-1(Hazardous Substances Data)

Usage

Description

2GBI (5418-95-1) is a selective and state-dependent blocker of voltage-gated proton channels (Hv1).1?2GBI blocks the channel by binding to the voltage-sensing domain from its intracellular side.2,3? Inhibition of Hv1 is a potentially new target of intervention in various pathophysiological processes including inflammatory, cancer, bone resorption and neurodegenerative disease.4

Chemical Properties

BROWN-PURPLE FINE CRYSTALLINE POWDER

Uses

N-1H-Benzimidazol-2-ylguanidine is used as a reagent in the synthesis of novel fused pyrimidines and imidazoles as potential analgesics.

References

1) Hong?et al. (2015),?Interrogation of the intersubunit interface if the open Hv1 proton channel with a probe of allosteric coupling; Sci. Rep.,?5?14077 2) Hong?et al.?(2014),?Molecular determinants of Hv1 proton channel inhibition by guanidine derivatives; Proc. Natl. Acad. Sci. USA,?111?9971 3) Gianti?et al. (2016),?On the role of water density fluctuations in the inhibition of a proton channel; Proc. Natl. Acad. Sci. USA,?113?E8359 4) Pupo and Gonzalez (2014),?In pursuit of an inhibitory drug for the proton channel; Proc. Natl. Acad. Sci. USA,?111?9673

InChI:InChI=1/C8H9N5/c9-7(10)13-8-11-5-3-1-2-4-6(5)12-8/h1-4H,(H5,9,10,11,12,13)/p+1

Upstream product

• 39145-59-0 o-phenylenediamine hydrochloride 
• 127099-85-8 N-Cyanoguanidine 
• 95-54-5 1,2-diamino-benzene 
• 127099-85-8 dicyandiamide 

Downstream Products

• 78650-08-5 4-Thiophen-2-yl-3,4-dihydro-benzo[4,5]imidazo[1,2-a][1,3,5]triazin-2-ylamine 
• 61678-05-5 2-Amino-s-triazino<1,2-a>benzimidazol 
• 55864-37-4 2-benzimidazolylcarbamonitrile 
• 24370-25-0 1-(1H-benzo[d]-imidazol-2-yl)urea 
• 305852-99-7 2-amino-4-(4'-fluorophenyl)-3,4-dihydro[1,3,5]triazino[1,2-a]benzimidazole 
• 380334-97-4 2-amino-4-(2'-fluorophenyl)-3,4-dihydro[1,3,5]triazino[1,2-a]benzimidazole 
• 52066-00-9 2-amino-4-oxo-3,4-dihydrobenzimidazo<1,2-a>-s-triazine 
• 199854-66-5 2,5-Bis[2-benzimidazolylimino]-3a,6a-diphenyl-1,2,3,3a,4,5,6,6a-octahydroimidazo[4,5-d]imidazole 
• 1060548-96-0 4-[(E)-2-(4-chlorophenyl)ethenyl][1,3,5]triazino[1,2-a]benzimidazol-2-amine 
• 1060548-98-2 4-[(E)-2-(4-dimethylaminophenyl)ethenyl][1,3,5]triazino[1,2-a]benzimidazol-2-amine 
• 1060549-02-1 {4-[(E)-2-(2-amino[1,3,5]triazino[1,2-a]benzimidazol-4-yl)ethenyl]phenoxy}acetic acid 
• 78650-16-5 2-amino-4-methyl-s-triazino[1,2-a]benzimidazole 
• 26958-67-8 4-phenyl-3,4-dihydrobenzo[4,5]imidazo[1,2-a][1,3,5]triazin-2-amine 
• 406928-23-2 4-(4-methylphenyl)-3,4-dihydro[1,3,5]triazino[1,2-a]benzimidazole-2-amine 

Relevant articles and documents

Cobalt-catalyzed isocyanide insertion cyclization to dihydrobenzoimidazotriazins

We have developed an isocyanide insertion reaction for the synthesis of dihydrobenzo[4,5]imidazo[1,2-a][1,3,5]triazins and imidazol-quinoxaline-5-carboxamides utilizing cobalt catalyst. Cobalt-catalyzed system is inexpensive and more acceptable from industrial point of view.

Design, synthesis, DFT studiesand anticancer activity of novel metal complexes containing 1,3,5-triazino[1,2-a]benzimidazole moiety using microwave as an approach for green chemistry

2-(2-amino-4,10-dihydrobenzo[4,5]imidazo[1,2-a][1,3,5]triazin-4-yl)phenol (ligand)and its related metal complexes of Mn (II), Co (II), Ni (II), Cu (II) and Zn (II)were prepared under microwave irradiation. The structures of prepared compounds were elucidated in terms of elemental analysis, FT-IR, UV-Vis, 1HNMR, 13CNMR, EPR spectra and mass spectra in addition to magnetic studies at room temperature and thermal properties. Elemental analysis results determined mole ratios between the ligand and metal 1:1 or 1:2. The microwave approach provides clean, shorter reaction times and enhancements in yields. Coats Redfern and Horowitz Metzger equation were used to study Thermal kinetic parameters of dehydration and decomposition of the complexes.The geometries of the ligand and its Mn (II), Co (II),Cu (II) and Zn (II) complexes were optimized using Gaussian 09 W; density functional theory (DFT) B3LYP method. Also, the cytotoxic activity of the ligand and its metal complexes were evaluated against liver cancer cells (HepG-2) and the Cu (II) complex exhibited the highest cytotoxic activity with promising IC50 value = 3.5μg/mlcompared to standard referencecisplatin.

Synthesis and Anti-inflammatory Screening of Some Mono and Bis-Alkoxyphthalimide Linked Benzimidazole and their Quinazoline and Pyrimidine Derivatives

In the present study, synthesis of some nonsymmetrical 2-(1H-benzimidazol-2-ylamino)-7,7-dimethyl-7,8-dihydroquinazolin-5(6H)-one (3) and substituted-(1H-benzo[d]imidazol-2-yl)amino-pyrimidine derivatives (4a, 4b, 4c and 5a, 5b) is described as a three-component reaction of 2-guanidinobenzimidazole (2) with triethyl orthoformate and different reactive methylene compounds. Subsequent condensation of compounds 3, 4a, 4b, 4c, and 5a, 5b with bromoethoxyphthalimide (1) gave final compounds 6, 7a, 7b, 7c, and 8a, 8b. Synthesized final compounds have been screened for their in-vivo anti-inflammatory activity against carrageenan-induced paw edema in albino rats. Diclofenac was used as standard anti-inflammatory agents. Some of the compounds exhibited significant anti-inflammatory activity, as compared to standard drug. Structures of synthesized compounds have been confirmed on the basis of chemical tests and spectral studies.