7621-86-5

Usage

Uses

2-(4-Aminophenyl)-1H-benzimidazol-5-amine is a useful as an aerogel lithium battery separator.

Safety Profile

Low toxicity by ingestion. Whenheated to decomposition it emits toxic vapors of NOx.

InChI:InChI=1/C13H12N4/c14-9-3-1-8(2-4-9)13-16-11-6-5-10(15)7-12(11)17-13/h1-7H,14-15H2,(H,16,17)

Synthetic route

5-nitro-2-(4-nitrophenyl)-1H-benzimidazole (1772-39-0) → 2-(4-aminophenyl)-5-amino-benzimidazole (7621-86-5)

Conditions	Yield
With sodium sulfide; phosphoric acid In water at 100℃; for 12h; pH=< 1;	96%
With hydrogenchloride; tin(ll) chloride

2',4',4-trinitrobenzanilide (37632-91-0) → 2-(4-aminophenyl)-5-amino-benzimidazole (7621-86-5)

Conditions	Yield
With 5%-palladium/activated carbon; hydrogen In ethanol at 80℃; under 60006 Torr; for 5h; Autoclave;	93.5%
With hydrogenchloride; tin(ll) chloride
With hydrogenchloride; tin(ll) chloride
Multi-step reaction with 2 steps 1: hydrogenchloride; iron / 90 - 95 °C 2: 250 °C / im Vakuum View Scheme

2',4',4-Triaminobenzanilide (60779-50-2) → 2-(4-aminophenyl)-5-amino-benzimidazole (7621-86-5)

Conditions	Yield
at 250℃; im Vakuum;
at 250℃; im Vakuum;

hydrogenchloride (7647-01-0) + 2',4',4-trinitrobenzanilide (37632-91-0) + SnCl2 → 2-(4-aminophenyl)-5-amino-benzimidazole (7621-86-5)

4-nitrobenzanilide (3460-11-5) → 2-(4-aminophenyl)-5-amino-benzimidazole (7621-86-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: sulfuric acid; nitric acid / 5 - 10 °C 3: 250 °C / im Vakuum View Scheme
Multi-step reaction with 3 steps 1: sulfuric acid; nitric acid / 5 - 10 °C 2: hydrogenchloride; iron / 90 - 95 °C 3: 250 °C / im Vakuum View Scheme

4-nitrobenzaldehdye (555-16-8) → 2-(4-aminophenyl)-5-amino-benzimidazole (7621-86-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid 2: SnCl2; aqueous methanol.HCl View Scheme

4-Nitrophenylene-1,2-diamine (99-56-9) → 2-(4-aminophenyl)-5-amino-benzimidazole (7621-86-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid 2: SnCl2; aqueous methanol.HCl View Scheme

benzene-1,2,4-triamine dihydrochloride (615-47-4) + 4-amino-benzoic acid (150-13-0) → 2-(4-aminophenyl)-5-amino-benzimidazole (7621-86-5)

Conditions	Yield
With methanesulfonic acid; tin(II) chloride dihdyrate In para-xylene; water for 8.25h; Solvent; Dean-Stark; Reflux; Inert atmosphere;

2,4-Dinitroanilin (97-02-9) → 2-(4-aminophenyl)-5-amino-benzimidazole (7621-86-5)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: Degussa F101 catalyst; hydrogen / ethanol / 2 h / 70 °C / 5171.62 Torr / Autoclave; Inert atmosphere 1.2: 15 °C 2.1: tin(II) chloride dihdyrate; methanesulfonic acid / para-xylene; water / 8.25 h / Dean-Stark; Reflux; Inert atmosphere View Scheme

4-nitro-benzoic acid (62-23-7) + 2,4-Dinitroanilin (97-02-9) → 2-(4-aminophenyl)-5-amino-benzimidazole (7621-86-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: boric acid / toluene / 6 h / Reflux 2: 5%-palladium/activated carbon; hydrogen / ethanol / 5 h / 80 °C / 60006 Torr / Autoclave View Scheme

2-(4-aminophenyl)-5-amino-benzimidazole (7621-86-5) + salicylaldehyde (90-02-8) → C27H20N4O2 (377059-64-8)

Conditions	Yield
In N,N-dimethyl-formamide at 50℃; for 4h; Inert atmosphere;	99%

2-(4-aminophenyl)-5-amino-benzimidazole (7621-86-5) + 4-(4'-nitrophenyl)benzoyl chloride (41567-99-1) → C39H26N6O6

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 24h;	78%

2-(4-aminophenyl)-5-amino-benzimidazole (7621-86-5) + 2-chloro-5-nitro-benzenesulfonic acid (96-73-1) → 4'-(5(6)-aminobenzimidazol-2-yl)-4-nitro-2-sulfodiphenylamine

Conditions	Yield
With magnesium oxide In N,N-dimethyl acetamide; water at 110 - 140℃; for 15h;

7,7'-methylenebis(2-phenyl-3,1-benzoxazin-4-one) + 2-(4-aminophenyl)-5-amino-benzimidazole (7621-86-5) → polymer; monomer(s): 7,7\-methylenebis(2-phenyl-3,1-benzoxazin-4-one); 5-amino-2-(4-aminophenyl)benzimidazole

Conditions	Yield
With phosphorus pentoxide In various solvent(s) at 20 - 180℃; for 10h;

2-(4-aminophenyl)-5-amino-benzimidazole (7621-86-5) + 4,4'-bis(chlorocarbonyl)diphenyl oxide (7158-32-9) → polymer; monomer(s): 4,4\-bis(chlorocarbonyl)diphenyl oxide; 5-amino-2-(4-aminophenyl)benzimidazole

Conditions	Yield
In N,N-dimethyl acetamide at -10 - 20℃;

2-(4-aminophenyl)-5-amino-benzimidazole (7621-86-5) + dianhydride of bis(3,4-dicarboxyphenyl)resorcinol ether → polymer; monomer(s): 5,5\-(1,3-phenylenedioxy)bis(1,3-isobenzofurandione); 5-amino-2-(4-aminophenyl)benzimidazole

Conditions	Yield
Stage #1: 2-(4-aminophenyl)-5-amino-benzimidazole; dianhydride of bis(3,4-dicarboxyphenyl)resorcinol ether In 1-methyl-pyrrolidin-2-one at 20℃; for 8h; Stage #2: With pyridine; acetic anhydride; triethylamine In 1-methyl-pyrrolidin-2-one at 20 - 60℃; for 12h;

2-(4-aminophenyl)-5-amino-benzimidazole (7621-86-5) + 4,4'-(1,1,1,3,3,3-hexafluoroisopropylidene)diphthalic anhydride (1107-00-2) → polymer, prepared by chemical condensation of polyamido acid; monomer(s): 5,5\-hexafluoroisopropylidenebis(1,3-isobenzofurandione); 5-amino-2-(4-aminophenyl)benzimidazole

Conditions	Yield
Stage #1: 2-(4-aminophenyl)-5-amino-benzimidazole; 4,4'-(1,1,1,3,3,3-hexafluoroisopropylidene)diphthalic anhydride In 1-methyl-pyrrolidin-2-one at 20℃; for 8h; Stage #2: With pyridine; acetic anhydride; triethylamine In 1-methyl-pyrrolidin-2-one at 20 - 60℃; for 12h;

2-(4-aminophenyl)-5-amino-benzimidazole (7621-86-5) + 4,4'-(1,1,1,3,3,3-hexafluoroisopropylidene)diphthalic anhydride (1107-00-2) → polymer, prepared by cyclodehydration of polyamido acid in N-methylpyrrolidone and toluene at 170 deg C; monomer(s): 5,5\-hexafluoroisopropylidenebis(1,3-isobenzofurandione); 5-amino-2-(4-aminophenyl)benzimidazole

Conditions	Yield
Stage #1: 2-(4-aminophenyl)-5-amino-benzimidazole; 4,4'-(1,1,1,3,3,3-hexafluoroisopropylidene)diphthalic anhydride In 1-methyl-pyrrolidin-2-one at 20℃; for 8h; Stage #2: In 1-methyl-pyrrolidin-2-one; toluene at 170℃;

2-(4-aminophenyl)-5-amino-benzimidazole (7621-86-5) → 4-amino-4'-(5(6)-aminobenzimidazol-2-yl)-2-sulfodiphenylamine

Conditions	Yield
Multi-step reaction with 2 steps 1: MgO / H2O; N,N-dimethyl-acetamide / 15 h / 110 - 140 °C 2: 55 percent / Fe, HCl / H2O View Scheme

Upstream product

• 37632-91-0 2',4',4-trinitrobenzanilide 
• 70142-79-9 4,4'-(terephthaloylbis(azanediyl))dibenzoic acid 
• 615-47-4 benzene-1,2,4-triamine dihydrochloride 
• 5922-25-8 N,N¹-(1,4-phenylene)bis(4-nitrobenzamide) 
• 106-50-3 1,4-phenylenediamine 
• 1772-39-0 6-nitro-2-(4-nitrophenyl)-1H-benzo[d]imidazole 
• 122-04-3 4-nitro-benzoyl chloride 
• 40655-18-3 2-(p-Nitrophenyl)-5-aminobenzimidazole 
• 555-16-8 4-nitrobenzaldehdye 
• 615-71-4 benzene-1,2,4-triamine 
• 87345-56-0 N,N'-terephthaloylbis(p-aminobenzoic acid) diphenyl ester 
• 62-23-7 4-nitro-benzoic acid 
• 97-02-9 2,4-Dinitroanilin 
• 150-13-0 4-amino-benzoic acid 

Downstream Products

• 1246468-45-0 (2S)-1-(phenylacetyl)-N-{4-[5-({[(2S)-1-(phenylacetyl)pyrrolidin-2-yl]carbonyl}amino)-1H-benzimidazol-2-yl]phenyl}pyrrolidine-2-carboxamide 
• 377059-64-8 C₂₇H₂₀N₄O₂ 

Relevant academic research and scientific papers

Synthesis method of 2-(4-aminophenyl)-5-aminobenzimidazole

The present invention provides a synthesis method of 2- (4-aminophenyl)-5-aminobenzimidazole, comprising the following steps: step 1, preparation of N,N'-bis (4-nitro - α- chlorinated) phenylmethylene p-phenylenediamine; step 2, using N, N'-bis(4-nitro - α- chloro) phenylmethylene p-phenylenediamine preparation N, N'-bis (4-nitro - α - imino) benzyl p-phenylenediamine; step 3, using N, N'-di (4-nitro - α - imino) benzyl p-phenylenediamine preparation 2- ( Step 4, 2-(4-nitro)phenyl-5-aminobenzimidazole was hydrogenated with a hydrogenation catalyst and hydrogen to give 2-(4-amino)phenyl-4-aminobenzimidazole. The present invention is intended to achieve a low production cost and high safety, less harmful pollutants 2- (4-aminophenyl) -5-aminobenzimidazole synthesis method.

Virtual screening identification and chemical optimization of substituted 2-arylbenzimidazoles as new non-zinc-binding MMP-2 inhibitors

Matrix metalloproteinases (MMPs) are a large family of zinc-dependent endoproteases known to exert multiple regulatory roles in tumor progression and invasiveness. This encouraged over the years the approach of MMP, and particularly MMP-2, targeting for anticancer treatment. Early generations of MMP inhibitors, based on aspecific zinc binding groups (ZBGs) assembled on (pseudo)peptide scaffolds, have been discontinued due to the clinical emergence of toxicity and further drawbacks, giving the way to inhibitors with alternative zinc-chelator moieties or not binding the catalytic zinc ion. In the present paper, we continue the search for new non-zinc binding MMP-2 inhibitors: exploiting previously identified compounds, a virtual screening (VS) campaign was carried out and led to the identification of a new class of ligands. The structure-activity relationship (SAR) of the benzimidazole scaffold was explored by synthesis of several analogues whose inhibition activity was tested with enzyme inhibition assays. By performing the molecular simplification approach, we disclosed different sets of single-digit micromolar inhibitors of MMP-2, with up to a ten-fold increase in inhibitory activity and ameliorated selectivity towards off-target MMP-8, compared to selected lead compound. Molecular dynamics calculations conducted on complexes of MMP-2 with docked privileged structures confirmed that analyzed inhibitors avoid targeting the zinc ion and dip inside the S1′ pocket. Present results provide a further enrichment of our insights for the design of novel MMP-2 selective inhibitors.

Preparation method of diamido nitrogen-containing aromatic heterocycle compound

The invention relates to the technical field of synthesis of compounds, in particular to a preparation method of diamido nitrogen-containing aromatic heterocycle compound. The preparation method includes mixing a compound having the structure as shown as the formula (I) with inorganic acid, reacting to obtain water-soluble organism, performing reduction reaction with a reducing agent sulfide to effectively reduce nitro-organism into amino-compounds, performing neutral reaction with alkali liquor so as to obtain the diamido nitrogen-containing aromatic heterocycle compound having the structureas shown as the formula (II) and having high yield and purity. The preparation method is simple and environmental friendly, is low in cost, needs mild reaction conditions, and is suitable to be popularized and applied in scale. According to tests, the yield of the diamido nitrogen-containing aromatic heterocycle compound prepared by the method is not lower than 90%, and even can reach 96%, and itspurity can reach 99.9%.

Synthesis method of amino substituted 2-phenylbenzimidazole derivative

The invention relates to a synthesis method of an amino substituted 2-phenylbenzimidazole derivative. The method uses cheap and easily available nitro substituted benzoic acid compound and dinitraniline compound as the raw materials for condensation to obtain an amide compound, then catalytic hydrogenation is carried out, and simultaneously cyclization is conducted to obtain the benzimidazole derivative. The reaction is green and efficient, the operation is simple and the yield is excellent.

PROCESS FOR THE PREPARATION OF AROMATIC AZOLE COMPOUNDS

Aromatic azole compounds such as 2-(4-aminophenyl)-5-amino-benzimidazole are prepared in an organic sulfonic acid solvent instead of polyphosphoric acid. This allows recovery and recycle of the solvent and avoids the handling and environmental concerns resulting from the use of polyphosphoric acid. The resulting compounds find use in the pharmaceutical industry, as anticorrosion agents, and as precursors for high-performance fibers having high strength, stiffness, and flame resistance.

HCV NS5A replication complex inhibitors. Part 3

In a recent disclosure,1 we described the discovery of dimeric, prolinamide-based NS5A replication complex inhibitors exhibiting excellent potency towards an HCV genotype 1b replicon. That disclosure dealt with the SAR exploration of the peripheral region of our lead chemotype, and herein is described the SAR uncovered from a complementary effort that focused on the central core region. From this effort, the contribution of the core region to the overall topology of the pharmacophore, primarily vector orientation and planarity, was determined, with a set of analogs exhibiting 50 in a genotype 1b replicon assay.

Benzimidazole compounds for regulating IgE

This invention relates to a family of phenylbenzimidazole analogs, which are inhibitors of the IgE response to allergens. These compounds are useful in the treatment of allergy and/or asthma or any diseases where IgE is pathogenic.

Benzimidazole derivatives as modulators of IgE

This invention relates to a family of benzimidazole analogs, which are inhibitors of the IgF response to allergens. These compounds are useful in the treatment of allergy, asthma, or any diseases where IgE is pathogenic.

Benzimidazole compounds for regulating IgE

This invention relates to a family of phenylbenzimidazole analogs, which are inhibitors of the IgE response to allergens. These compounds are useful in the treatment of allergy and/or asthma or any diseases where IgE is pathogenic.

Benzimidazole derivatives as modulators of IgE

This invention relates to a family of diacyl benzimidazole analogs, which are inhibitors of the IgE response to allergens. These compounds are useful in the treatment of allergy and/or asthma or any diseases where IgE is pathogenic.