6154-30-9

Usage

Uses

Used in Pharmaceutical Synthesis:
2,5-dibromo-4-nitro-1H-imidazole is used as an intermediate in the synthesis of pharmaceuticals for its ability to be incorporated into various drug molecules, enhancing their therapeutic properties.
Used in Agrochemical Production:
In the agrochemical industry, 2,5-dibromo-4-nitro-1H-imidazole is used as an intermediate in the development of compounds that help protect crops from pests and diseases, leveraging its antimicrobial and antifungal properties.
Used in Specialty Polymers:
2,5-dibromo-4-nitro-1H-imidazole is utilized in the production of specialty polymers, where its unique structure and reactivity contribute to the creation of polymers with specific properties for various applications.
Used as a Reagent in Organic Synthesis:
2,5-dibromo-4-nitro-1H-imidazole also serves as a reagent in organic synthesis, facilitating specific chemical reactions that are crucial for the formation of complex organic molecules.
Safety Considerations:
It is important to handle 2,5-dibromo-4-nitro-1H-imidazole with care due to its potentially hazardous nature if not properly managed, ensuring safe laboratory practices and disposal methods are followed.

InChI:InChI=1/C3HBr2N3O2/c4-1-2(8(9)10)7-3(5)6-1/h(H,6,7)

Upstream product

• 6963-65-1 5-bromo-4-nitro-1H-imidazole 
• 40507-59-3 5⁽⁴⁾-nitro-1⁽³⁾H-imidazole-4⁽⁵⁾-carboxylic acid 
• 7726-95-6 bromine 
• 6963-65-1 4-bromo-5-nitro-1H-imidazole 
• 64591-03-3 2,4-dibromo-1H-imidazole 
• 3034-38-6 1H-4⁽⁵⁾-nitroimidazole 

Downstream Products

• 162759-90-2 2,4-dibromo-1-methyl-5-nitro-1H-imidazole 
• 72255-86-8 2,5-dibromo-1-methyl-4-nitroimidazole 
• 65902-59-2 2-bromo-4-nitro-1H-imidazole 
• 15965-32-9 2,5-dichloro-4-nitro-1H-imidazole 

Relevant academic research and scientific papers

Efficient Access to Original 6-Substituted 5-Nitro-2,3-dihydro-imidazo[2,1- b ]oxazoles

A one-pot sequential intramolecular cyclization and Suzuki-Miyaura or Sonogashira reaction under microwave irradiation are reported in the 5-nitro-2,3-dihydroimidazo[2,1- b ]oxazole series. The intramolecular cyclization of 1-(2,4-dibromo-5-nitro-1 H -imidazol-1-yl)propan-2-ol between the hydroxyethyl group and the bromine atom at the 2-position is carried out first, followed by optimization and generalization of the Suzuki-Miyaura and Sonogashira cross-coupling reactions of the bromine atom at the 4-position. The various boronic acids and alkynyl derivatives used to perform these palladium-catalyzed cross-coupling reactions allowed to substitute the 6-position of 5-nitro-2,3-dihydroimidazo[2,1- b ]oxazole compounds.

An improved kilogram-scale synthesis of 2-bromo-4-nitro-1H-imidazole: A key building block of nitroimidazole drugs

An efficient two-step method for the synthesis of 2-bromo-4-nitroimidazole, 6, a key building block for nitroimidazole drugs, has been developed. The synthesis involves dibromination of 4-nitroimidazole 10 followed by selective debromination using in situ reductive deiodination strategy. The reactions are facile, safe, and easy to scale up. The large-scale applicability of this improved method was tested by conducting the reactions on kilogram scale to produce the desired product in high yield and quality.

A concise and sequential synthesis of the nitroimidazooxazole based drug, Delamanid and related compounds

A concise, protection-group free and sequential route has been developed for the synthesis of the nitroimidazole based FDA-approved multi-drug resistant anti-tuberculosis drug, Delamanid and anti-leishmanial lead candidate VL-2098. The synthesis required

An efficient one-pot catalyzed synthesis of 2,4-disubstituted 5-nitroimidazoles displaying antiparasitic and antibacterial activities

A one-pot regioselective bis-Suzuki-Miyaura or Suzuki-Miyaura/Sonogashira reaction on 2,4-dibromo-1-methyl-5-nitro-1H-imidazole under microwave heating was developed. This method is applicable to a wide range of (hetero)arylboronic acids and terminal alkynes. Additionally, this approach provides a simple and efficient way to synthesize 2,4-disubstituted 5-nitroimidazole derivatives with antibacterial and antiparasitic properties.

Bicyclic nitroimidazole derivatives, preparation method thereof and pharmaceutical composition for prevention or treatment of tuberculosis containing the same as an active ingredient

The present invention relates to a bicyclic nitroimidazole derivative or a pharmaceutically acceptable salt thereof, a method for manufacturing the same, and a pharmaceutical composition comprising the same for preventing or treating tuberculosis. The novel bicyclic nitroimidazole derivative according to the present invention shows a superior antitubercular efficacy for tubercular bacillus in various environments, thereby can be used as a pharmaceutical composition for preventing or treating the tuberculosis.

METHOD FOR PRODUCING 4-NITROIMIDAZOLE COMPOUND

The present invention provides a method for producing a 4-nitroimidazole compound represented by general formula (1) at high yield and at high purity by a safe method causing few dangers such as explosion. The production method of the present invention comprises iodinating a 4-nitroimidazole compound represented by general formula (2): wherein each of X1 and X2 represents a chlorine atom or bromine atom, and then reducing the obtained 5-iodo-4-nitroimidazole compound represented by general formula (3): wherein X2 is the same as defined above.

1-SUBSTITUTED 4-NITROIMIDAZOLE COMPOUND AND PROCESS FOR PRODUCING THE SAME

The present invention relates to a 1-substituted-4-nitroimidazole compound represented by the general formula (1) or a salt thereof, (wherein R is a hydrogen atom, a lower alkoxy group-substituted lower alkyl group, a phenyl-lower alkoxy group-substituted lower alkyl group, a cyano-substituted lower alkyl group, a phenyl-lower alkyl group which may have lower alkoxy groups as the substituents in the phenyl ring or a group of the formula -CH2RA; X is a halogen atom or a group of the formula -S(O)n-R1) and method for preparing the same. The compound of the formula (1) is a useful compound as an intermediate for synthesis of various pharmaceutical and agricultural chemicals, particularly, as intermediates for antitubercular agents.