5213-49-0

Usage

Uses

Used in Pharmaceutical Industry:
2,4-dinitro-3H-imidazole is used as a synthetic reagent for the production of (S)-PA 824 (P122500), a novel anti-tuberculosis drug. Its role in the synthesis process is crucial for developing new and effective treatments against tuberculosis, a disease that continues to pose significant health challenges worldwide.
As a chemical intermediate, 2,4-dinitro-3H-imidazole can also be utilized in the development of other pharmaceutical compounds, potentially expanding its applications in the medical field. Its unique structure and properties make it a valuable building block for the creation of new drugs with diverse therapeutic applications.

InChI:InChI=1/C3H2N4O4/c8-6(9)2-1-4-3(5-2)7(10)11/h1H,(H,4,5)

Upstream product

• 19182-81-1 1,4-dinitro-1H-imidazole 
• 3034-38-6 1H-4⁽⁵⁾-nitroimidazole 
• 131394-05-3 1-(2,4-Dinitro-imidazol-1-yl)-propan-2-one 

Downstream Products

• 73332-79-3 2-methyl-5-nitro-2,3-dihydro-imidazo[2,1-b]oxazole 
• 73332-80-6 2-chloromethyl-5-nitro-2,3-dihydro-imidazo[2,1-b]oxazole 
• 73332-76-0 2-chloromethyl-2,3-dihydro-6-nitroimidazo[2,1-b]oxazole 
• 127692-22-2 2-Butyl-2-methyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazole 
• 127692-19-7 2-Isopropoxymethyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazole 
• 127692-18-6 6-Nitro-2-trichloromethyl-2,3-dihydro-imidazo[2,1-b]oxazole 
• 127692-15-3 5-Nitro-2-phenyl-2,3-dihydro-imidazo[2,1-b]oxazole 
• 127692-14-2 6-Nitro-2-phenyl-2,3-dihydro-imidazo[2,1-b]oxazole 
• 127692-21-1 6-Nitro-2-phenoxymethyl-2,3-dihydro-imidazo[2,1-b]oxazole 
• 73332-73-7 1-(2,4-dinitro-imidazol-1-yl)-propan-2-ol 
• 92918-19-9 2-(2,4-Dinitro-imidazol-1-yl)-propan-1-ol 
• 73332-75-9 2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole 
• 73334-41-5 1-chloro-3-(2,4-dinitro-imidazol-1-yl)-propan-2-ol 
• 127692-17-5 2-Bromomethyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazole 

Relevant academic research and scientific papers

Synthesis, thermal hazard analysis and density functional theory study of nitroimidazoles

To understand the thermal decomposition mechanism and performance of nitroimidazoles, 1,4-dinitroimidazole (1,4-DNI), 2,4-dinitroimidazole (2,4-DNI) and 4,5-dinitroimidazole (4,5-DNI) were synthesized by 4-nitroimidazole firstly and all of them were studied using Differential Scanning Calorimetry (DSC), Accelerating Rate Calorimetry (ARC) and Density Functional Theory (DFT). The experiments show that among the four nitroimidazoles, the decomposition temperature and apparent activation energy of 1,4-DNI are relatively low. Theoretical calculations show that compared with C[sbnd]NO2, N[sbnd]NO2 is easier to break from the imidazole ring, and the detonation performance of 1,4-DNI is the best among the four nitroimidazoles. Dinitroimidazoles all contain two nitro groups, resulting in their sensitivity and energy much greater than 4-NI. Since 1,4-DNI is the only substance containing N[sbnd]NO2, the chemical activity of 1,4-DNI is further improved. In addition, 1,4-DNI has relatively excellent detonation performance, which can be used as the research direction of new energetic materials.

Programmed synthesis of triarylnitroimidazoles via sequential cross-coupling reactions

Transition-metal-catalyzed programmed sequential arylation reactions of 2-chloro-4-nitro-1H-imidazoles were achieved. The methods are general and were applied in a chemoselective manner for the synthesis of different multiarylated 4-nitroimidazoles bearing three different aryl groups. A salient feature is Pd-catalyzed hetero-hetero coupling at the C5 position through a NO2 directed cross-dehydrogenative coupling (CDC) approach.

Design and Synthesis of Energetic Materials towards Versatile Applications by N-trinitromethyl and N-nitromethyl Functionalization of Nitroimidazoles

Modifying the properties of energetic materials is important not only for gaining insight into the relationship between structures and properties but also for multiple applications. A new family of energetic compounds, polynitroimidazoles featuring trinitromethyl, nitromethyl and methyl acetate moieties at the nitrogen position of heterocyclic rings were synthesized. The high-energy oxidizers 2-nitro and 4-nitro-1-(trinitromethyl)-1H-imidazoles were obtained by nitration of 1-acetonylpolynitroimidazoles in fuming HNO3 and concentrated H2SO4. 4,5-Dinitro-1-(nitromethyl)-1H-imidazole and 4,5-dinitro-1-(acetate methyl)-1H-imidazole were afforded by using 68 % HNO3 and concentrated H2SO4 through controllable synthesis. All the intermediates and the target compounds were confirmed by X-ray diffraction. It is noteworthy that one of the N-trinitromethyl nitroimidazole derivatives showed high density (ρ: 1.88 g cm?3), attractive positive oxygen balance (Ω: +18.3 %) and good detonation performance (D: 9003 m s?1) exceeding those of ADN, while N-nitromethyl derivative behaved higher thermal stability and lower sensitivity in contrast to those of NG. N-acetate methyl derivative gave an interesting melt-castable property (Tm.p.: 86 oC, Td: 224 oC), acceptable detonation performance as well as low sensitivity towards impact and friction (IS>40 J, FS>360 N), making it a competitive replacement for DNAN. These chemical and physical properties indicate that these novel materials show promising energetic performance towards future applications.

Synthesis and purification method of 2, 4-dinitroimidazole

The invention discloses a synthesis and purification method of 2, 4-dinitroimidazole, and aims to acquire 2, 4-dinitroimidazole, increase yield and make the purification purity meet the requirements of medicinal purity. An adopted technical scheme includes: adding 4-nitroimidazole raw material and concentrated sulfuric acid into an acetic anhydride solvent respectively under an ice bath environment and carrying out reaction, utilizing 4-nitroimidazole as the preparation raw material to carry out nitration reaction with sodium nitrate so as to nitrify 4-nitroimidazole into 1, 4-dinitroimidazole, and dissolving the obtained 1, 4-dinitroimidazole in a benzene derivative solvent to carry out thermal rearrangement reaction to obtain 2, 4-dinitroimidazole, and using a mixed solvent to conduct recrystallization purification, thus obtaining 2, 4-dinitroimidazole.

1,3-diaminoguanidine-2,4,5-trinitroimidazole salt and preparation method thereof

The invention discloses a 1,3-diaminoguanidine-2,4,5-trinitroimidazole salt and a preparation method thereof, belongs to the technical field of organic energetic materials and aims at solving the problem in the prior art that a TNT-based melt-cast explosive harms the environment in the use process. The method comprises the steps of using imidazole as a reaction raw material to generate 2,4,5-trinitroimidazole through step-by-step nitrification; enabling a nitrification product to react with a potassium carbonate/potassium chloride solution to form a salt to prepare 2,4,5-trinitroimidazole potassium salt; and finally obtaining a target product 1,3-diaminoguanidine-2,4,5-trinitroimidazole salt through double-decomposition reaction of 1,3-diamino guanidine hydrochloride and the 2,4,5-trinitroimidazole potassium salt. The preparation method is simple, low in preparation cost and good in security; and the final product 1,3-diaminoguanidine-2,4,5-trinitroimidazole salt is high in purity.

SUBSTITUTED 1,2,3-TRIAZOL-1-YL-METHYL-2,3-DIHYDRO-2-METHYL-6-NITROIMIDAZO[2,1-B]OXAZOLES AS ANTI-MYCOBACTERIAL AGENTS AND A PROCESS FOR THE PREPARATION THEREOF

The present invention relates to new generation of triazole functionality containing 6-nitro-2,3-dihydroimidazooxazole agents for general formula I, their method of preparation and their use as drugs for treatment of tuberculosis, MDR-TB and XDR-TB either

Synthesis of new generation triazolyl- and isoxazolyl-containing 6-nitro-2,3-dihydroimidazooxazoles as anti-TB agents: In vitro, structure-activity relationship, pharmacokinetics and in vivo evaluation

The nitroimidazole scaffold has attracted great interest in the last decade, which ultimately led to the discovery of the successful drug Delamanid for multi-drug resistant tuberculosis (MDR-TB). Herein, we report medicinal chemistry on a 6-nitro-2,3-dihy

Design, synthesis, antibacterial evaluation and docking study of novel 2-hydroxy-3-(nitroimidazolyl)-propyl-derived quinolone

A novel series of 2-hydroxy-3-(nitroimidazolyl)-propyl-derived quinolones 6a-o were synthesized and evaluated for their in vitro antibacterial activity. Most of the target compounds exhibited potent activity against Gram-positive strains. Among them, moxifloxacin analog 6n displayed the most potent activity against Gram-positive strains including S. epidermidis (MIC = 0.06 μg/mL), MSSE (MIC = 0.125 μg/mL), MRSE (MIC = 0.03 μg/mL), S. aureus (MIC = 0.125 μg/mL), MSSA (MIC = 0.125 μg/mL), (MIC = 2 μg/mL). Its activity against MRSA was eightfold more potent than reference drug gatifloxacin. Finally, docking study of the target compound 6n revealed that the binding model of quinolone nucleus was similar to that of gatifloxacin and the 2-hydroxy-3-(nitroimidazolyl)-propyl group formed two additional hydrogen bonds. A novel series of 2-hydroxy-3-(nitroimidazolyl)-propyl derived quinolones 6a-o were synthesized and tested for their antibacterial activity. Moxifloxacin analog 6n showed potent activity against all tested strains (MIC = 0.03-2 μg/mL).

6-NITRO-2,3-DIHYDROIMIDAZO[2,1-b]OXAZOLES AND A PROCESS FOR THE PREPARATION THEREOF

The present invention relates to newer generation of triazoles, tetrazoles, isoxazoles, urea and sulphonamide functionalities containing 6-nitro-2, 3-dihydronitroimidazooxazoles agents of formula 1, their method of preparation, and their use as drugs for

Metal salts of dinitro-, trinitropyrazole, and trinitroimidazole

The syntheses of alkali and earth alkaline dinitropyrazolate (DNP), trinitropyrazolate (TNP), and trinitroimidazolate (TNI) salts are reported. Additionally, copper trinitroimidazolate was synthesized. Their characterization by NMR spectroscopy, mass spectrometry, elemental analysis, and vibrational spectroscopy is reported as well. Crystal structures of compound Ba(DNP)2 (9), which crystallizes with one molecule of methanol and ethyl ether as well as of compounds Sr(TNP)2·3H2O (12), Ba(TNP)2·3H2O (13), and LiTNI·3H2O (14) were determined. The energetic and thermal properties were measured as well. Green- and red-burning pyrotechnic formulations containing barium salts 9 and 13 as well as strontium salts 8 and 12 serving as colorants are tested. Additionally, formulations using Sr(TNP)2·3H2O (12) and Ba(TNP)2·3H2O (13) as the oxidizer and colorant at the same time were examined. The formulations were investigated with regard to their combustion behavior and performances such as burn time, dominant wavelength, spectral purity, luminous intensity, and luminous efficiency. The sensitivities towards ignition stimuli and the decomposition temperatures were determined as well.