95-23-8

Basic information

• Product Name: 5-Amino-1,3-dihydro-2H-benzimidazol-2-one
• Synonyms: 5-AMINO-2-BENZIMIDAZOLINONE;5-AMINO-2-HYDROXYBENZIMIDAZOLE;5-AMINOBENZIMIDAZOLINONE;5-AMINOBENZIMIDAZOLONE;5-AMINO-1,3-DIHYDRO-2H-BENZIMIDAZOL-2-ONE;5-AMINO-1,3-DIHYDRO-BENZOIMIDAZOL-2-ONE;5(6)-AMINOBENZOIMIDAZOLONE;AKOS BBS-00006487
• CAS NO: 95-23-8
• Molecular Formula: C₇H₇N₃O
• Molecular Weight: 149.15
• EINECS: 202-401-8
• Product Categories: Intermediates of Dyes and Pigments;BENZIMIDAZOLE;Benzimidazole Series;Imidazol&Benzimidazole;Miscellaneous
• Mol File: 95-23-8.mol
• Article Data: 10

Chemical Properties

• Melting Point: >300 °C
• Boiling Point: 201.4 °C at 760 mmHg
• Flash Point: 75.6 °C
• Appearance: /
• Density: 1.363 g/cm³
• Vapor Pressure: 0.308mmHg at 25°C
• Refractive Index: 1.657
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 11.80±0.30(Predicted)
• CAS DataBase Reference: 5-Amino-1,3-dihydro-2H-benzimidazol-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Amino-1,3-dihydro-2H-benzimidazol-2-one(95-23-8)
• EPA Substance Registry System: 5-Amino-1,3-dihydro-2H-benzimidazol-2-one(95-23-8)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-36-22
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 95-23-8(Hazardous Substances Data)

Usage

Chemical Properties

Crystalline powder

Uses

5-Amino-2-hydroxybenzimidazole is an important reagent in the discovery of potent and selective non-nucleotide small molecule inhibitors of CD73

InChI:InChI=1/C7H7N3O/c8-4-1-2-5-6(3-4)10-7(11)9-5/h1-3H,8H2,(H2,9,10,11)

Upstream product

• 93-84-5 5-nitro-2,3-dihydro-1H-benzimidazol-2-one 
• 99-56-9 4-Nitrophenylene-1,2-diamine 
• 7647-01-0 hydrogenchloride 
• 35411-68-8 ethyl N-(2,4-dinitrophenylcarbamate) 

Downstream Products

• 1031051-39-4 7-(2-hydroxybenzoyl)-1,3-dihydro-2H-imidazo[4,5-g]quinolin-2-one 
• 1111735-35-3 5-[2-(4-trifluoromethyl-phenyl)-ethylamino]-1,3-dihydro-benzoimidazol-2-one 
• 343615-76-9 C₂₃H₂₈N₄O₅S 
• 339293-46-8 2-chloro-N-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)-acetamide 
• 1395886-00-6 5-((4-((2-chlorophenyl)amino)pyrimidin-2-yl)amino)-1H-benzo[d]imidazol-2(3H)-one hydrochloride 

Relevant articles and documents

Synthetic method for preparing 5-aminobenzimidazolone

The invention discloses a synthesis method for preparing 5-aminobenzimidazolone (TM), which comprises the following steps: firstly, carrying out diazotization reaction on aniline to prepare aniline diazonium salt; secondly, coupling the aniline diazonium salt with o-phenylenediamine to generate an azo compound, and carrying out a reaction on the azo compound and urea under the catalysis of concentrated sulfuric acid to generate an azobenzimidazolone compound, and subjecting the azobenzimidazolone compound to a hydrogenation reduction reaction to obtain the target compound 5-aminobenzimidazolone. The method disclosed by the invention is simple in process, high in selectivity and high in product yield, all used reactants are utilized, and the method has very high atom economy. The use of a nitration reagent concentrated nitric acid is avoided, the wastewater and the generation of salt in the wastewater are greatly reduced, and the method is a green production process. In addition, the hydrocracking reduction operation is simple, no other iron mud such as iron powder reduction is generated, no waste residue is basically generated, the quality of a finished product is obviously improved, filter-pressing rinsing water can be repeatedly used for more than multiple times, the cost is reduced, and the environmental pollution is reduced.

Chemoselective Hydrogenation of Nitroaromatics at the Nanoscale Iron(III)–OH–Platinum Interface

Catalytic hydrogenation of nitroaromatics is an environment-benign strategy to produce industrially important aniline intermediates. Herein, we report that Fe(OH)x deposition on Pt nanocrystals to give Fe(OH)x/Pt, enables the selective hydrogenation of nitro groups into amino groups without hydrogenating other functional groups on the aromatic ring. The unique catalytic behavior is identified to be associated with the FeIII-OH-Pt interfaces. While H2 activation occurs on exposed Pt atoms to ensure the high activity, the high selectivity towards the production of substituted aniline originates from the FeIII-OH-Pt interfaces. In situ IR, X-ray photoelectron spectroscopy (XPS), and isotope effect studies reveal that the Fe3+/Fe2+ redox couple facilitates the hydrodeoxygenation of the -NO2 group during hydrogenation catalysis. Benefitting from FeIII-OH-Pt interfaces, the Fe(OH)x/Pt catalysts exhibit high catalytic performance towards a broad range of substituted nitroarenes.

Oxidative Cyclization-Induced Activation of a Phosphoinositide 3-Kinase Inhibitor for Enhanced Selectivity of Cancer Chemotherapeutics

In this work, we designed a prodrug that reacts with cellular oxidative equivalents leading to ether cleavage and cyclization to release an active phosphatidylinositol 3-kinase (PI3K) inhibitor. We show that the compound reduces affinity for PI3KA relative to the PI3K inhibitor, is slow to intercellularly oxidize, and is resistant to liver microsomes. We observed modest activity in untreated acute myeloid leukemia cells and 14-fold selectivity relative to non-cancerous cells. The cellular activity of the compound can be modulated by the addition of antioxidants or oxidants, indicating the compound activity is sensitive to cellular reactive oxygen species (ROS) state. Co-treatment with cytosine arabinoside or doxorubicin was used to activate the compound inside cells. We observed strong synergistic activity specifically in acute myeloid leukemia (AML) cancer cells with an increase in selective anticancer activity of up to 90-fold. Thus, these new self-cyclizing compounds can be used to increase the selectivity of anticancer agents.