5381-78-2

Basic information

• Product Name: 1H-Benzimidazole,1-methyl-5-nitro-(9CI)
• Synonyms: 1H-Benzimidazole,1-methyl-5-nitro-(9CI);1-methyl-5-nitro-1H-1,3-benzimidazole;1H-benzimidazole, 1-methyl-5-nitro-;1-methyl-5-nitro-1H-benzimidazole;1-methyl-5-nitrobenzimidazole;1-methyl-5-nitro-benzimidazole;1-Methyl-5-nitro-1H-benzo[d]iMidazole;1-N-Methyl-5-nitroindazole
• CAS NO: 5381-78-2
• Molecular Formula: C₈H₇N₃O₂
• Molecular Weight: 177.162
• Product Categories: BENZIMIDAZOLE
• Mol File: 5381-78-2.mol
• Article Data: 7

Chemical Properties

• Melting Point: 210-212°
• Boiling Point: 358.6°Cat760mmHg
• Flash Point: 170.7°C
• Appearance: /
• Density: 1.42g/cm³
• Vapor Pressure: 2.52E-05mmHg at 25°C
• Refractive Index: 1.676
• PKA: 3.39±0.10(Predicted)
• CAS DataBase Reference: 1H-Benzimidazole,1-methyl-5-nitro-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Benzimidazole,1-methyl-5-nitro-(9CI)(5381-78-2)
• EPA Substance Registry System: 1H-Benzimidazole,1-methyl-5-nitro-(9CI)(5381-78-2)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 5381-78-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H7N3O2/c1-10-5-9-7-4-6(11(12)13)2-3-8(7)10/h2-5H,1H3

Upstream product

• 553-90-2 Dimethyl oxalate 
• 94-52-0 5-nitrobenzimidazole 
• 1632-83-3 1-Methylbenzimidazole 
• 124-38-9 carbon dioxide 
• 99-56-9 4-Nitrophenylene-1,2-diamine 
• 51-17-2 benzoimidazole 
• 74-88-4 methyl iodide 
• 94-52-0 6-nitro-1H-benzo[d]imidazole 

Downstream Products

• 82040-15-1 3-Methyl-6-nitro-1-[2-(4-nitro-phenyl)-2-oxo-ethyl]-3H-benzoimidazol-1-ium; bromide 
• 85721-83-1 1-methyl-2-benzoyl-5-nitrobenzimidazole 
• 85510-68-5 1-methyl-3-benzoyl-5-nitro-2-(1-methyl-5-nitro-2-benzimidazolyl)-2-benzimidazol-4-ine 
• 82040-12-8 1-methyl-5-nitro-3-phenacylbenzimidazolium bromide 
• 1190604-03-5 3-methyl-8-phenyl-3H-imidazo[4',5':3,4]benzo[c]isoxazole 
• 1190604-04-6 8-(4-chlorophenyl)-3-methyl-3H-imidazo[4,',5':3,4]benzo[c]isoxazole 
• 10394-38-4 1-methyl-1H-benzo[d]imidazol-5-amine 
• 26530-93-8 1-methyl-6-amino-1H-benzo[d]imidazole 
• 1234801-39-8 (2-{[(4E)-2-amino-1-oxaspiro[4.5]dec-2-en-4-ylidene]amino}-4-nitrophenyl)methylformamide 
• 1234801-38-7 (2-{[(3E)-5-amino-2,2-dimethylfuran-3(2H)-ylidene]amino}-4-nitrophenyl)methylformamide 
• 82040-26-4 N-methyl-4-nitro-2-(4-(4-nitrophenyl)-1H-imidazol-1-yl)aniline 
• 82040-21-9 N-methyl-4-nitro-2-(4-phenyl-1H-imidazol-1-yl)aniline 
• 15965-66-9 2-chloro-1-methyl-5-nitro-1H-benzoimidazole 
• 66108-85-8 1-methyl-5-nitro-1,3-dihydro-2H-benzo[d]imidazol-2-one 

Relevant articles and documents

Endogenous X-C=O species enable catalyst-free formylation prerequisite for CO2reductive upgrading

CO2, the main component of greenhouse gas, is currently developed as a promising surrogate of carbon feedstock. Among various conversion routes, CO2undergoing catalytic reduction can furnish hydrogen/energy carriers and value-added chemicals, while specific metal-containing catalysts or organocatalysts are often prerequisite for smooth proceeding of the involved reaction processes. In this work, both formic acid and N-containing benzoheterocyclic compounds (including various benzimidazoles, benzothiazole, and benzoxazole) along with silanols could be synthesized with high yields (>90%) from catalyst-free reductive upgrading of CO2under mild conditions (50 °C). The endogenous X-CO species, derived from the N-methyl-substituted amide-based solvent [Me2N-C(O)-R], especially PolarClean, and O-formyl group [O-C(O)-H] of in situ formed silyl formate, were found to play a prominent promotional role in the activation of the used hydrosilane for reductive CO2insertion, as demonstrated by density functional theory (DFT) calculations and isotopic labeling experiments. Moreover, reaction mechanisms and condition-based sensitivity assessment were also delineated.

Fusion of 2-(furan-2-yl)thiazole to 1-methyl-1H-benzimidazole

Methylation of 5(6)-nitro-1H-benzimidazole with methyl iodide in the presence of potassium hydroxide and N-methylpyrrolidin-2-one gave a mixture of isomeric 1-methyl-5-nitro- and 1-methyl-6-nitro-1H-benzimidazoles which were reduced with tin in concentrated aqueous HCl on heating. The resulting amines reacted with furan-2-carbonyl chloride in N-methylpyrrolidin-2-one to give furan-2-carboxamides which were treated with excess P2S5 in pyridine. Oxidation of isomeric furan-2-carbothioamides with K3[Fe(CN)6] in alkaline medium afforded a mixture of intramolecular cyclization products, 2-(furan-2-yl)-6-methyl-6H-imidazo[4,5-g][1,3]benzothiazole and 2-(furan-2-yl)-8-methyl-8H-imidazo[4,5-g][1,3]benzothiazole which were separated by column chromatography and identified.

ANTIFUNGAL AGENTS

Compounds of formula (I), and pharmaceutically acceptable salts thereof, may be used in therapy, for example as antifungal agents: (I) wherein: Rl, R2, R3, R4, R5, R6, R7, X and X1 are as defined herein. Certain compounds of formula (I) are also provided. Compounds of formula (T), and agriculturally acceptable salts thereof, may also be used as agricultural fungicides.