7621-86-5

Basic information

• Product Name: 2-(4-Aminophenyl)-1H-benzimidazol-5-amine
• Synonyms: 2-(4-AMINOPHENYL)-5-AMINOBENZIMIDAZOLE;2-(4-AMINOPHENYL)-1H-BENZIMIDAZOL-5-AMINE;2-(4-aminophenyl)-1h-benzimidazol-5-amin;2-(4-aminophenyl)-1H-benzimidazol-2-amine;5-Amino-2-(4-aminophenyl)benzimidazole;2-(4-AMINOPHENYL)-1H-BENZIMIDAZOL-6-AMINE;5-Amino-2-(4-aminophenyl) 1H-benz-imidazole;2-(4-Aminophenyl)-3H-benzimidazole-5-amine
• CAS NO: 7621-86-5
• Molecular Formula: C₁₃H₁₂N₄
• Molecular Weight: 224.26
• EINECS: 231-538-6
• Product Categories: Intermediates of Dyes and Pigments;API intermediates
• Mol File: 7621-86-5.mol
• Article Data: 13

Chemical Properties

• Melting Point: 234.0 to 238.0 °C
• Boiling Point: 355.66°C (rough estimate)
• Flash Point: 317.6 °C
• Appearance: /
• Density: 1.2067 (rough estimate)
• Vapor Pressure: 5.88E-12mmHg at 25°C
• Refractive Index: 1.5890 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 11.15±0.10(Predicted)
• CAS DataBase Reference: 2-(4-Aminophenyl)-1H-benzimidazol-5-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-Aminophenyl)-1H-benzimidazol-5-amine(7621-86-5)
• EPA Substance Registry System: 2-(4-Aminophenyl)-1H-benzimidazol-5-amine(7621-86-5)

Safety Data

• RTECS: DD5421200
• Hazardous Substances Data: 7621-86-5(Hazardous Substances Data)

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 
• 1772-39-0 5-nitro-2-(4-nitrophenyl)-1H-benzimidazole 
• 60779-50-2 2',4',4-Triaminobenzanilide 
• 7647-01-0 hydrogenchloride 
• 70142-79-9 4,4'-(terephthaloylbis(azanediyl))dibenzoic acid 
• 615-47-4 benzene-1,2,4-triamine dihydrochloride 
• 122-04-3 4-nitro-benzoyl chloride 
• 1772-39-0 6-nitro-2-(4-nitrophenyl)-1H-benzo[d]imidazole 
• 106-50-3 1,4-phenylenediamine 
• 5922-25-8 N,N¹-(1,4-phenylene)bis(4-nitrobenzamide) 
• 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 articles and documents

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.

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%.

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.