162759-90-2

Basic information

• Product Name: 2,4-DIBROMO-1-METHYL-5-NITRO-1H-IMIDAZOLE
• Synonyms: 2,4-DIBROMO-1-METHYL-5-NITRO-1H-IMIDAZOLE
• CAS NO: 162759-90-2
• Molecular Formula: C₄H₃Br₂N₃O₂
• Molecular Weight: 284.89352
• Mol File: 162759-90-2.mol

Chemical Properties

• Boiling Point: 360.4±45.0 °C(Predicted)
• Appearance: /
• Density: 2.51±0.1 g/cm3(Predicted)
• PKA: -3.92±0.60(Predicted)
• CAS DataBase Reference: 2,4-DIBROMO-1-METHYL-5-NITRO-1H-IMIDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-DIBROMO-1-METHYL-5-NITRO-1H-IMIDAZOLE(162759-90-2)
• EPA Substance Registry System: 2,4-DIBROMO-1-METHYL-5-NITRO-1H-IMIDAZOLE(162759-90-2)

Safety Data

• Hazardous Substances Data: 162759-90-2(Hazardous Substances Data)

Usage

Uses

Used in Agricultural Industry:
2,4-DIBROMO-1-METHYL-5-NITRO-1H-IMIDAZOLE is used as a fungicide and bactericide for protecting crops from various diseases. Its potent biocidal activity makes it effective against a range of pathogens that can damage or destroy agricultural produce.
However, due to its high toxicity and potential environmental impact, the use of 2,4-DIBROMO-1-METHYL-5-NITRO-1H-IMIDAZOLE is heavily regulated and controlled. It is crucial to handle and store this compound with extreme caution and in accordance with safety guidelines to prevent inhalation or ingestion, which can lead to severe health complications.

Upstream product

• 186581-53-3 diazomethane 
• 6154-30-9 2,4⁽⁵⁾-dibromo-5⁽⁴⁾-nitroimidazole 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 162759-92-4 4-bromo-1-methyl-5-nitro-1H-2-imidazolecarbonitrile 
• 59177-47-8 4-bromo-1-methyl-5-nitro-1H-imidazole 

Relevant articles and documents

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.

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.

Nucleophilic substitution studies on nitroimidazoles, and applications to the synthesis of biologically active compounds

The rationalization of the synthesis of substituted analogs of megazol, a biologically active 5-nitroimidazole at position 4 of the imidazole ring, had led to the study of intermediate steps. The methylation by diazomethane of 2,4-(5)dihalogeno-5-(4)nitroimidazole is regioselective leading to 2,4- dihalogeno-1-methyl-5-nitroimidazole 2. On this compound 2, hard nucleophiles such as cyanide, methoxide or hydride anions react only with the halogen at the 2 position; whereas soft nucleophiles such as amine, thiol or trifluoromethyl anion from an organocopper species react only with the halogen at position 4 in the intermediate 3b or compound 4b.