3034-42-2

Basic information

• Product Name: 1-METHYL-5-NITROIMIDAZOLE
• Synonyms: 1H-Imidazole, 1-methyl-5-nitro-;1-methyl-5-nitro-imidazol;Imidazole, 1-methyl-5-nitro-;1-Methyl-5-nitroimidazole >97.0% (HPLC);Metronidazole Impurity 4
• CAS NO: 3034-42-2
• Molecular Formula: C₄H₅N₃O₂
• Molecular Weight: 127.1014
• EINECS: 221-225-2
• Product Categories: Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 3034-42-2.mol
• Article Data: 16

Chemical Properties

• Melting Point: 54-57 °C
• Boiling Point: 328.9 °C at 760 mmHg
• Flash Point: 152.7 °C
• Appearance: /
• Density: 1.44 g/cm³
• Vapor Pressure: 0.000352mmHg at 25°C
• Refractive Index: 1.618
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 2.13±0.10(Predicted)
• BRN: 123550
• CAS DataBase Reference: 1-METHYL-5-NITROIMIDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-METHYL-5-NITROIMIDAZOLE(3034-42-2)
• EPA Substance Registry System: 1-METHYL-5-NITROIMIDAZOLE(3034-42-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• RTECS: NI7530000
• Hazardous Substances Data: 3034-42-2(Hazardous Substances Data)

Usage

Chemical Properties

Pale Yellow Solid

Uses

1-Methyl-5-nitroimidazole is used in the synthesis of new 5-nitroimidazoles as potential antibacterial drugs via VNS procedure.

InChI:InChI=1/C4H5N3O2/c1-6-3-5-2-4(6)7(8)9/h2-3H,1H3

Upstream product

• 616-47-7 1-methyl-1H-imidazole 
• 186581-53-3 diazomethane 
• 60-29-7 diethyl ether 
• 3034-38-6 1H-4⁽⁵⁾-nitroimidazole 
• 77-78-1 dimethyl sulfate 
• 553-90-2 Dimethyl oxalate 
• 3034-38-6 5-nitro-1H-imidazole 
• 80-48-8 methyl p-toluene sulfonate 
• 74-88-4 methyl iodide 
• 67-56-1 methanol 
• 5709-48-8 acetic acid (4-nitroimidazol-1-yl)methyl ester 
• 212248-40-3 1-Chloro-4-nitroimidazole 
• 13182-96-2 3-(4-nitro-1H-imidazol-1-yl)propanenitrile 
• 109540-97-8 1-methyl-5-nitroimidazole-4-carboxylic acid 

Downstream Products

• 936-05-0 1-methyl-2-hydroxymethyl-5-nitroimidazole 
• 116248-38-5 1-methyl-4-phenylsulfonylmethyl-5-nitro-1H-imidazole 
• 116248-39-6 1-methyl-2-phenylsulfonylmethyl-5-nitroimidazole 
• 85869-03-0 2-benzoyl-1-methyl-5-nitroimidazole 
• 85869-04-1 (4-Chloro-phenyl)-(1-methyl-5-nitro-1H-imidazol-2-yl)-methanone 
• 56-40-6 glycine 
• 74-89-5 methylamine 
• 69709-39-3 4-methoxy-1-nitro-2-[(phenylsulfonyl)methyl]benzene 
• 89303-18-4 2-Benzenesulfonylmethyl-4-fluoro-1-nitro-benzene 
• 1146349-20-3 4-(4-fluorobenzenesulfonylmethyl)-1-methyl-5-nitro-1H-imidazole 
• 3034-43-3 1,3-dimethyl-4-nitroimidazolium iodide 

Relevant articles and documents

Reactivity of reduced [2Fe-2S] ferredoxins parallels host susceptibility to nitroimidazoles

The kinetics of the electron transfer reaction between reduced [2Fe-2S] ferredoxins and select nitroimidazole antimicrobial agents is reported. The ferredoxins from the protozoan Trichomonas vaginalis and the cyanobacterium Anabaena sp. strain 7120 were studied because they are the proximal electron donors to nitroimidazoles in these two organisms with significantly different nitroimidazole susceptibilities. The rates of electron transfer from Anabaena ferredoxin to all nitroimidazoles were 1 to 2 orders of magnitude lower than for T. vaginalis ferredoxin. Quantitative structure-activity analysis of the kinetic data showed that the size of the alkyl substituent on the N-1 position of the imidazole ring strongly influenced the magnitude of the electron transfer rate constant. This implies that the distance between the iron-sulfur cluster and the nitro group of the imidazole is the critical variable in determining the rate of electron transfer. A correlation between the magnitude of the one-electron transfer rate constant with the susceptibility of the host organism to the cytotoxic effects of nitroimidazoles was also discovered. These results demonstrate that reductive activation is the most crucial step in determining the toxicity of nitroimidazoles.

Synthesis, crystal structure and antibacterial activity of new highly functionalized ionic compounds based on the imidazole nucleus

Several new highly functionalized imidazolium derivatives were synthesized, via appropriate synthetic routes, using imidazole, 1-methylimidazole and 2-phenyl-1-methylimidazole as key intermediates. The antibacterial activity of the prepared compounds was evaluated against: Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa and Salmonella thipymurium using disk-diffusion and MIC methods. Crystal X-ray structures are reported for six compounds.

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.