59177-47-8

Basic information

• Product Name: 4-Bromo-1-methyl-5-nitro-1H-imidazole
• Synonyms: 1-Methyl-4-bromo-5-nitro-1H-imidazole;4-Bromo-1-methyl-5-nitro-1H-imidazole;4-Bromo-5-nitro-1-methyl-1H-imidazole
• CAS NO: 59177-47-8
• Molecular Formula: C₄H₄BrN₃O₂
• Molecular Weight: 205.9975
• Mol File: 59177-47-8.mol

Chemical Properties

• Boiling Point: 333.9°Cat760mmHg
• Flash Point: 155.7°C
• Appearance: /
• Density: 2.04g/cm³
• Vapor Pressure: 0.000257mmHg at 25°C
• Refractive Index: 1.688
• CAS DataBase Reference: 4-Bromo-1-methyl-5-nitro-1H-imidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromo-1-methyl-5-nitro-1H-imidazole(59177-47-8)
• EPA Substance Registry System: 4-Bromo-1-methyl-5-nitro-1H-imidazole(59177-47-8)

Safety Data

• Hazardous Substances Data: 59177-47-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C4H4BrN3O2/c1-7-2-6-3(5)4(7)8(9)10/h2H,1H3

Upstream product

• 6963-65-1 5-bromo-4-nitro-1H-imidazole 
• 77-78-1 dimethyl sulfate 
• 6963-65-1 4-bromo-5-nitro-1H-imidazole 
• 7664-93-9 sulfuric acid 
• 162759-90-2 2,4-dibromo-1-methyl-5-nitro-1H-imidazole 
• 186581-53-3 diazomethane 

Downstream Products

• 40648-96-2 1-methyl-4-nitro-1H-imidazole-5-carbonitrile 
• 32057-98-0 1-methyl-5-nitro-4-phenylthioimidazole 
• 113121-62-3 1-methyl-4-(4'-methylphenyl)thio-5-nitroimidazole 

Relevant articles and documents

Synthesis and in vitro antibacterial activity of new 2-(1-methyl-4-nitro- 1H-imidazol-5-ylsulfonyl)-1,3,4-thiadiazoles

In the present study we report the synthesis and antibacterial activity of a new series 2-(1-methyl-4-nitro-1H-imidazol-5-ylsulfonyl)-1,3,4-thiadiazoles (6a-c). Compounds 6a-c were tested in vitro by the conventional agar dilution method against a panel of microorganisms including gram-negative and gram-positive bacteria. Compound 6b with 5-(5-nitrofuran-2-yl)-residue on 1,3,4-thiadiazole scaffold have shown promising antibacterial activities against gram-positive bacteria including Staphylococcus aureus, Staphylococcus epidermidis and Bacillus subtilis.

Compounds containing 2-substituted imidazole ring for treatment against human African trypanosomiasis

A series of compounds containing 2-substituted imidazoles has been synthesized from imidazole and tested for its biological activity against human African trypanosomiasis (HAT). The 2-substituted 5-nitroimidazoles such as fexinidazole (7a) and 1-[4-(1-methyl-5-nitro-1H-imidazol-2-ylmethoxy)-pyridin-2- yl-piperazine (9e) exhibited potent activity against T. brucei in vitro with low cytotoxicity and good solubility. The presence of the NO2 group at the 5-position of the imidazole ring in 2-substituted imidazoles is the crucial factor to inhibit T. brucei.

Synthesis and In-vitro antibacterial activity of 5-substituted 1-methyl-4-nitro-1H-imidazoles

A series of 5-substituted 1-methyl-4-nitro-1H-imidazole derivatives were synthesized and evaluated for in-vitro antibacterial activity against a panel of microorganisms including Staphylococcus aureus, Staphylococcus epidermidis, Bacillus subtilis, Esherichia coli, Klebsiella pneumonia, Entrobacter aerogenes, and Helicobacter pylori using conventional agar dilution method. Among the test compounds, 1-methyl-4-nitro-5-(phenylsulfonyl)-1H-imidazole was the most potent against Gram-positive bacteria, with a MIC value of ≤8 μg/mL. All compounds showed no significant activity against Gram-negative bacteria at concentrations ≤64 μg/mL The MIC values against 15 clinical isolates of H. pylori indicated that compounds 10 and 11 were the most active compounds in this series in terms of inhibiting the growth of H. pylori (MIC = 2 μg/mL). It was also demonstrated that their corresponding activities were four times larger than that of metronidazole.

Nucleophilic substitution studies on nitroimidazoles, and applications to the synthesis of biologically active compounds

The rationalization of the synthesis of substituted analogs of megazol, a biologically active 5-nitroimidazole at position 4 of the imidazole ring, had led to the study of intermediate steps. The methylation by diazomethane of 2,4-(5)dihalogeno-5-(4)nitroimidazole is regioselective leading to 2,4- dihalogeno-1-methyl-5-nitroimidazole 2. On this compound 2, hard nucleophiles such as cyanide, methoxide or hydride anions react only with the halogen at the 2 position; whereas soft nucleophiles such as amine, thiol or trifluoromethyl anion from an organocopper species react only with the halogen at position 4 in the intermediate 3b or compound 4b.

A New and Unequivocal Method for Establishing the Position of N-Glycosylation of Unsymmetrically C-Substituted Imidazoles

N-Substitution of an unsymmetrically C-substituted imidazole can give rise to a pair of structurally isomeric derivatives and to differentiate between such related compounds can be difficult.Two methods, one spectroscopic and one chemical, for ascertaining the orientation of such N-substitutions are described, with particular application to the establishment of the direction of N-ribosidation of a series of halogeno nitroimidazoles.