19183-14-3

Basic information

• Product Name: 4,5-Dinitroimidazole
• Synonyms: 4,5-Dinitroimidazole;4,5-Dinitro-1H-imidazole
• CAS NO: 19183-14-3
• Molecular Formula: C₃H₂N₄O₄
• Molecular Weight: 158.07
• Product Categories: Imidaxoles
• Mol File: 19183-14-3.mol
• Article Data: 11

Chemical Properties

• Melting Point: 187-188 °C
• Boiling Point: 561.2 °C at 760 mmHg
• Flash Point: 293.2 °C
• Appearance: /
• Density: 1.867 g/cm³
• Vapor Pressure: 4.77E-12mmHg at 25°C
• Refractive Index: 1.676
• PKA: 3.41±0.10(Predicted)
• CAS DataBase Reference: 4,5-Dinitroimidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5-Dinitroimidazole(19183-14-3)
• EPA Substance Registry System: 4,5-Dinitroimidazole(19183-14-3)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 19183-14-3(Hazardous Substances Data)

Usage

General Description

4,5-Dinitroimidazole is a chemical compound that belongs to the nitroimidazole class of organic compounds. It is a yellow crystalline solid with the molecular formula C3H3N5O4. 4,5-Dinitroimidazole is commonly used as a high energy density material and as a precursor in the synthesis of pharmaceuticals and other organic compounds. Due to its explosive nature, 4,5-Dinitroimidazole is used in the production of energetic materials, such as propellants, explosives, and pyrotechnics. Additionally, it has potential applications in the field of medicine as an antimicrobial and antiparasitic agent, making it an important substance in both the chemical and pharmaceutical industries.

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

Upstream product

• 131394-04-2 1-(4,5-Dinitro-imidazol-1-yl)-propan-2-one 
• 19182-81-1 1,4-dinitro-1H-imidazole 
• 3034-38-6 1H-4⁽⁵⁾-nitroimidazole 

Downstream Products

• 1451007-65-0 1-(2,4,6-trinitrophenyl)-4,5-dinitroimidazole 
• 1451007-67-2 1-(3,5-diamino-2,4,6-trinitrophenyl)-4,5-dinitroimidazole 
• 1451007-66-1 1-(3-amino-2,4,6-trinitrophenyl)-4,5-dinitroimidazole 
• 1220996-01-9 tetraphenylphosphonium 4,5-dinitroimidazolate 
• 1220996-13-3 ethyltriphenylphosphonium 4,5-dinitroimidazolate 
• 1220996-25-7 N-phenylpyridinium 4,5-dinitroimidazolate 
• 1141447-74-6 C₁₁H₉N₃O₃ 
• 573986-91-1 5-(2-aminoethylamino)-4-nitro-1H-imidazole 
• 6963-64-0 4(5)-Mercapto-5(4)-nitroimidazole 
• 57531-38-1 4-chloro-5-nitroimidazole 
• 82039-90-5 4⁽⁵⁾-Nitro-5⁽⁴⁾-aminoimidazole 
• 127925-84-2 2-(4,5-Dinitro-imidazol-1-yl)-1-(4-iodo-phenyl)-ethanone 
• 127925-86-4 2-(4,5-Dinitro-imidazol-1-yl)-1-(4-methoxy-phenyl)-ethanone 
• 127925-81-9 2-(4,5-Dinitro-imidazol-1-yl)-1-(4-fluoro-phenyl)-ethanone 

Relevant articles and documents

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In search of ionic liquids incorporating azolate anions

Twenty-eight novel salts with tetramethyl-, tetraethyl-, and tetrabutylammonium and 1-butyl-3-methylimidazolium cations paired with 3,5-dinitro-1,2,4-triazolate, 4-nitro-1,2,3-triazolate, 2,4-dinitroimidazolate, 4,5-dinitroimidazolate, 4,5-dicyanoimidazolate, 4-nitroimidazolate, and tetrazolate anions have been prepared and characterized by using differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), and single-crystal X-ray crystallography. The effects of cation and anion type and structure on the physicochemical properties of the resulting salts, including several ionic liquids, have been examined and discussed. Ionic liquids (defined as having m.p. 4mim]+) and the heterocyclic azolate anions studied, and with several combinations of tet raethyl or tetrabutylammonium cations and the azolate anions. The [C4mim] + azolates were liquid at room temperature exhibiting large liquid ranges and forming glasses on cooling with glasstransition temperatures in the range of -53 to -82°C (except for the 3,5-dinitro-1,2,4-triazolate salt with m.p. 33°C). Six crystal structures of the corresponding tetraalkylammonium salts were determined and the effects of changes to the cations and anions on the packing of the structure have been investigated.

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.

Method for preparing 4, 5-dinitroimidazole by adopting microchannel reactor

The invention discloses a method for preparing 4, 5-dinitroimidazole by adopting a microchannel reactor. According to the method, raw material mixing is enhanced by using a micromixer, and the mixinguniformity is limited by uneven flow fields generated by stirring in a prior reactor; a flow focusing technology adopted by the HPIMM micromixer can force two fluid thin layers to flow through a convergence chamber so as to generate efficient and uniform thin layer contact reaction, and the stoichiometric ratio of reactants is precisely controlled, so that the consumption of strong acid is reducedfrom the source, and the generation of multi-nitration byproducts caused by acid amount and temperature change during the reaction in a prior kettle reactor is eliminated, mass transfer resistance iseliminated, generation of hot spots is avoided, and the problem that the 4, 5-dinitroimidazole has great safety problems caused by intense heat release in the prior reactor is solved. According to the invention, a microsystem is utilized to carry out the synthesis of 4-nitroimidazole and 4, 5-dinitroimidazole, the yields can reach to 96.1% and 92.4%.