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
• Article Data: 3

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

General Description

2,4-DIBROMO-1-METHYL-5-NITRO-1H-IMIDAZOLE is a highly reactive and toxic chemical compound. It is a derivative of imidazole, containing two bromine atoms and a nitro group. The presence of these functional groups makes it a potent biocide and pesticide. It is commonly used in agriculture, particularly as a fungicide and bactericide, to protect crops from various diseases. However, due to its toxicity and potential environmental impact, its usage is heavily regulated and controlled. Inhalation or ingestion of this compound can be harmful and may lead to severe health complications, making it imperative to handle and store it with caution and in accordance with safety guidelines.

Upstream product

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

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.

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.