Description

2-Bromo-4-nitroimidazole (CAS No. 65902-59-2) is a high-purity nitroimidazole derivative with the molecular formula C₃H₂BrN₃O₂. This heterocyclic organic compound is characterized by a bromo substituent at the 2-position and a nitro group at the 4-position of the imidazole ring, making it a valuable intermediate in pharmaceutical and agrochemical synthesis. With a molecular weight of 191.97 g/mol, it is supplied as a crystalline solid with >98% purity (HPLC), ensuring consistency for research and industrial applications. Ideal for nucleophilic substitution reactions, this compound is rigorously tested for impurities (GC/MS, NMR) and is packaged under inert conditions to guarantee stability. Suitable for use in medicinal chemistry, radiopharmaceutical labeling, and as a precursor for antimicrobial agents.

Properties

• CAS Number: 65902-59-2
• Complexity: 125
• IUPAC Name: 2-bromo-5-nitro-1H-imidazole
• InChI: InChI=1S/C3H2BrN3O2/c4-3-5-1-2(6-3)7(8)9/h1H,(H,5,6)
• InChI Key: UWRJWMLKEHRGOH-UHFFFAOYSA-N
• Exact Mass: 190.93304
• Molecular Formula: C3H2BrN3O2
• Molecular Weight: 191.97
• SMILES: C1=C(NC(=N1)Br)[N+](=O)[O-]
• Topological: 74.5
• Monoisotopic Mass: 190.93304
• Synonyms: 2-Bromo-4-nitroimidazole, 613-851-3, 65902-59-2, 2-BROMO-4-NITRO-1H-IMIDAZOLE, 2-Bromo-5-nitro-1H-imidazole, 2-Bromo-4-nitro-3H-imidazole, C3H2BrN3O2, MFCD09038915, 1H-Imidazole, 2-bromo-4-nitro-, 2-BROMO-5-NITROIMIDAZOLE, nitrobromoimidazole, MFCD09025308, SCHEMBL59059, SCHEMBL3188625, DTXSID60216120, BCP21680, CS-D0919, CL2228, SBB054453, AKOS005259859, AKOS015833823, AB49571, AC-6399, FB55690, AS-17659, SY011513, DB-031682, B3503, NS00035928, EN300-195253, 2-Bromo-4-nitro-1H-imidazole;2-Bromo-5-nitro-1H-imidazole

Application

2-Bromo-4-nitroimidazole serves as a key building block in the synthesis of nitroimidazole-based antibiotics and antiprotozoal drugs, particularly for targeting anaerobic pathogens. Its reactive bromo and nitro groups facilitate the development of radiotracers for hypoxia imaging in oncology research. The compound is also utilized in agrochemical research for designing novel fungicides and herbicides.

Safety and Hazards

GHS Hazard Statements

• H302+H312+H332 (25%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]
• H302 (50%): Harmful if swallowed [Warning Acute toxicity, oral]
• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (75%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 4 (50%)
• Skin Irrit. 2 (100%)
• Eye Irrit. 2A (100%)
• STOT SE 3 (75%)

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Disclaimer: Sold exclusively for laboratory research. Prohibited for commercial use, diagnostics, or human/animal applications. Buyers assume all compliance liability.