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Usage

Uses

Used in Pharmaceutical Industry:
4-Methyl-5-nitroimidazole is used as a mutagen for [application reason] causing mutations with Klebsiella pneumonia and Salmonella typhimurium. This property makes it valuable in the study of genetic mutations and the development of new pharmaceuticals.
Used in Chemical Synthesis:
4-Methyl-5-nitroimidazole is used as a trapping agent for [application reason] the reactive 1:1 intermediate formed during the reaction between triphenylphosphine and dibenzoylacetylene. This application is crucial in the synthesis of various complex organic compounds.
Used in Organic Chemistry:
4-Methyl-5-nitroimidazole is used as a starting reagent for [application reason] the synthesis of pyrazole derivatives. Pyrazole derivatives have a wide range of applications, including pharmaceuticals, agrochemicals, and materials science.
Used in Materials Science:
4-Methyl-5-nitroimidazole is used in the fabrication of [application type] zeolitic imidazolate frameworks (ZIFs) for [application reason] their unique properties, such as high porosity and tunable pore sizes, which make them suitable for applications like gas storage, catalysis, and drug delivery.

InChI:InChI=1/C9H8ClN/c10-9-6-2-1-4-8(9)5-3-7-11/h1-2,4,6H,3,5H2

Upstream product

• 822-36-6 4-methyl-1H-imidazole 
• 86760-83-0 5-methyl-1,4-dinitro-1H-imidazole 
• 88657-81-2 cis-bis(ethylenediamine)(4-methylimidazole)chlorocobalt(III)⁽²⁺⁾ 

Downstream Products

• 69195-93-3 4-nitro-5-styryl-1⁽³⁾H-imidazole 
• 6307-17-1 4-nitro-5-styryl-1⁽³⁾H-imidazole 
• 7464-68-8 1,5-dimethyl-4-nitro-1H-imidazole 
• 57658-79-4 1,4-dimethyl-5-nitro-1H-imidazole 
• 25271-84-5 5-methyl-1⁽³⁾H-imidazol-4-ylamine 
• 302-72-7 rac-Ala-OH 
• 69195-93-3 5-nitro-4-(2-phenylethenyl)-1H-imidazole 
• 99686-99-4 1-benzyl-5-methyl-4-nitro-1H-imidazole 
• 99687-00-0 1-benzyl-4-methyl-5-nitroimidazole 
• 7664-41-7 ammonia 
• 602279-03-8 [2-(tert-butylamino)-4-(4-methyl-5-nitro-1H-imidazol-1-yl)-5-phenyl-3-furyl]phenyl methanone 
• 6307-17-1 5⁽⁴⁾-nitro-4⁽⁵⁾-styrylimidazole 
• 323582-18-9 4-nitro-1-p-methoxybenzyl-5-methylimidazole 
• 1245556-14-2 3-(5-methyl-4-nitro-1H-imidazol-1-yl)propanenitrile 

Relevant academic research and scientific papers

Reactions of 1,4-dinitroimidazoles with hydrazines

Reaction of 2-methyl-1,4-dinitroimidazole with hydrazine results in expansion of the imidazole ring and formation of the 1.2.4-triazine derivative. Reaction of 1,4-dinitroimidazole with N-aminomorpholine yields 1-(N-morpholino)-4-nitroimidazole, by degenerative transformation of the imidazole ring. Treatment of 1,4-dinitroimidazoles with t-butoxycarbonylhydrazine results in the break down of the imidazole ring and formation of glyoxal dihydrazone derivatives. Structures of representative heterocyclic products were determined by X-ray analysis.

Light-Controlled Tyrosine Nitration of Proteins

Tyrosine nitration of proteins is one of the most important oxidative post-translational modifications in vivo. A major obstacle for its biochemical and physiological studies is the lack of efficient and chemoselective protein tyrosine nitration reagents. Herein, we report a generalizable strategy for light-controlled protein tyrosine nitration by employing biocompatible dinitroimidazole reagents. Upon 390 nm irradiation, dinitroimidazoles efficiently convert tyrosine residues into 3-nitrotyrosine residues in peptides and proteins with fast kinetics and high chemoselectivity under neutral aqueous buffer conditions. The incorporation of 3-nitrotyrosine residues enhances the thermostability of lasso peptide natural products and endows murine tumor necrosis factor-α with strong immunogenicity to break self-tolerance. The light-controlled time resolution of this method allows the investigation of the impact of tyrosine nitration on the self-assembly behavior of α-synuclein.

Synthesis and biological activity of nitro heterocycles analogous to megazol, a trypanocidal lead

As part of our efforts to develop new compounds aimed at the therapy of parasitic infections, we synthesized and assayed analogues of a lead compound megazol, 5-(1-methyl-5-nitro-1H-2-imidazolyl)-1,3,4-thiadiazol-2-amine, CAS no. 19622-55-0), in vitro. We first developed a new route for the synthesis of megazol. Subsequently several structural changes were introduced, including substitutions on the two rings of the basic nucleus, replacement of the thiadiazole by an oxadiazole, replacement of the nitroimidazole part by a nitrofurane or a nitrothiophene, and substitutions on the exocyclic nitrogen atom for evaluation of an improved import by the glucose or the purine transporters. Assays of the series of compounds on the protozoan parasites Trypanosoma brucei, Trypanosoma cruzi, and Leishmania donovani, as either extracellular cells or infected macrophages, indicated that megazol was more active than the derivatives. Megazol was then evaluated on primates infected with Trypanosoma brucei gambiense, including late-stage central nervous system infections in combination with suramin. Full recovery was observed in five monkeys in the study with no relapse of parasitemia within a 2 year follow-up. Because there is a lack of efficacious treatments for sleeping sickness in Africa and Chagas disease in South America, megazol is proposed as a potential alternative. The mutagenicity of this compound is at present being reevaluated, and metabolism is also under investigation prior to possible further developments.

NITROIMIDAZOLES. PART XIII. HYDROLYSIS OF 1,4-DINITROIMIDAZOLES IN WATER SOLUTIONS OF SULFURIC ACID

The kinetics of the hydrolysis of 1,4-dinitroimidazole in aqueous solutions of sulfuric acid of four concentrations from 9 to 40percent, at 25 deg C, has been investigated using UV-VIS spectrophotometric method.The mechanism of the reaction has been proposed.

Electrophilic substitution reactions in heterocycles complexed to exchange-inert metal ions. (Ethylenediamine)cobalt(III) complexes of imidazole and histidine

(Ethylenediamine)cobalt(III) complexes of imidazole and histidine are nitrated under mild conditions with a standard HNO3-H2SO4 nitrating mixture. In contrast to the more robust pentaamminecobalt(III) complexes, the nitrated imidazole ligand readily dissociates, providing an excellent synthetic route to a variety of nitroimidazoles. Pyridine coordinated to either Co(NH3)53+ or Co(en)2Cl2+ is not nitrated, even under conditions that destroy the complex. The difference in reactivity is evidently a reflection of the Co(III) d electron interaction with the lowest unoccupied molecular orbital (LUMO) of the ligand. The nucleophilic displacement of a nitro group by chloride in a coordinated nitroimidazole is also observed. Crystal data for bis(ethylenediamine)(benzimidazole)chlorocobalt(III) perchlorate, space group P1, Z = 4, a = 8.168 (4) ?, b = 11.570 (4) ?, c = 21.162 (8) ?, α = 78.93 (2)°, β = 78.87 (2)°, γ = 69.24 (2)°, and R = 6.67% for 3437 reflections; for bis(ethylenediamine)(pyridine)chlorocobalt(III) chloride, space group P21/n, a = 8.489 (3) ?, b = 14.021 (6) ?, c = 12.670 (6) ?, α = 90.0°, β = 91.63 (2)°, γ = 90.0°, and R = 4.11% for 2185 reflections; for bis(ethylenediamine)(4-nitroimidazolato)chlorocobalt(III) chloride hydrate, space group P1, a = 8.603 (5) ?, b = 7.358 (3) ?, c = 14.287 (7) ?, α = 95.82 (2)°, β = 86.79 (2)°, γ = 115.39 (2)°, and R = 5.21% for 5903 reflections; for bis(ethylenediamine)(4-chloroimidazole)chlorocobalt(III) chloride, space group C2/c, Z = 8, a = 23.550 (6) ?, b = 11.805 (2) ?, c = 12.128 (3) ?, α = 90.0°, β = 115.92 (2)°, γ = 90.0°, and R = 4.34% for 2377 reflections; and for (ethylenediamine)(4-nitrohistidinato-O,N,N′)chlorocobalt(III) hydrate, space group P21/n, a = 8.544 (3) ?, b = 17.382 (5) ?, c = 10.256 (3) ?, α = 90.0°, β = 107.50 (2)°, γ = 90.0°, and R = 5.60% for 2556 reflections, are reported.

1,4-Dinitroimidazole and Derivatives. Structure and Thermal Rearrangement

Nitration of 4-nitroimidazole in acetic anhydride/glacial acetic acid gives 1,4-dinitroimidazole.The crystal and molecular structure of this compound have been determined by direct methods.Crystals are orthorombic; P212121, a 5.853(3), b 9.591(8), c 10.392(5) Angstroem, V 583.4(7) Angstroem3, Dm 1.76 g cm-1, Dc 1.80 g cm-1 (Z = 4); λ 0.71069 Angstroem; T 173 K.The structure was refined to R = 0.048 for 926 reflections 2?(I)>.Both 2-methyl-2-nitro- and 5-methyl-4-nitroimidazoles N-nitrate under the same conditions.When heated in solution at 100 -140 deg C 1,4-dinitro- and 2-methyl-1,4-dinitro-imidazoles rearrange to give C-nitro isomers and some denitration products, but 5(4)-methyl-1,4(5)-dinitroimidazole failed to give identifiable products.

1,2(1,4)-dimethyl-4(2)-(2-hydroxyethyl)-5-nitro-imidazole antiprotozoal agents with reduced mutagenicity

A group of 4-substituted-5-nitroimidazoles is described, having effective antiprotozoal activity with much less mutagenicity than is shown by known 5-nitroimidazoles.