121816-84-0

Usage

Uses

Used in Chemical Research:
4-Bromo-2-nitro-1H-imidazole is used as a research compound for its unique chemical properties, including high volatility and reactivity. It is employed in various chemical reactions and studies to understand its behavior and potential applications in different fields.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Bromo-2-nitro-1H-imidazole is used as an intermediate compound in the synthesis of various drugs. Its unique structure and reactivity make it a valuable component in the development of new medications and therapeutic agents.
Used in Material Science:
4-Bromo-2-nitro-1H-imidazole is used as a building block in the development of new materials with specific properties. Its reactivity and structural characteristics allow for the creation of novel compounds with potential applications in various industries, such as electronics, coatings, and adhesives.
Used in Environmental Applications:
4-Bromo-2-nitro-1H-imidazole is used as a chemical in environmental remediation processes. Its reactivity can be harnessed to break down or neutralize harmful substances, contributing to the development of more sustainable and eco-friendly solutions for waste management and pollution control.

InChI:InChI=1/C3H2BrN3O2/c4-2-1-5-3(6-2)7(8)9/h1H,(H,5,6)

Synthetic route

4-bromo-2-nitro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole → 4-bromo-2-nitro-1H-imidazole (121816-84-0)

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 20℃; for 24h;	67.5%

4-bromo-1-(triphenylmethyl)-1H-imidazole (87941-55-7) → triphenylmethyl alcohol (76-84-6) + 4-bromo-2-nitro-1H-imidazole (121816-84-0) + 4,5'-Dibromo-2'-nitro-1H,3'H-[2,4']biimidazolyl (121816-85-1)

Conditions	Yield
With hydrogenchloride; n-butyllithium; propyl nitrate 1) hexane, THF, 0 deg C, 1 h; 2) 20 deg C, 2 h; 3) MeOH; Yield given. Multistep reaction;

4-bromo-2-nitro-1H-imidazole (121816-84-0) + dimethyl sulfate (77-78-1) → 4-bromo-1-methyl-2-nitroimidazole (121816-79-3) + 4,5'-Dibromo-3'-methyl-2'-nitro-1H,3'H-[2,4']biimidazolyl (121816-86-2)

Conditions	Yield
With potassium carbonate In acetone for 0.5h; Heating; Yields of byproduct given;	A 37% B n/a
In 1,4-dioxane for 7h; Heating; Yields of byproduct given;	A n/a B 0.17 g

4-bromo-2-nitro-1H-imidazole (121816-84-0) → 2-amino-4-bromoimidazole

Conditions	Yield
With palladium on activated charcoal; acetic acid In tert-butyl alcohol
With palladium on activated charcoal; hydrogen; acetic acid In tert-butyl alcohol
With palladium on activated charcoal; acetic acid In tert-butyl alcohol Inert atmosphere;

Upstream product

• 87941-55-7 4-bromo-1-(triphenylmethyl)-1H-imidazole 

Downstream Products

• 121816-79-3 4-bromo-1-methyl-2-nitroimidazole 
• 121816-86-2 4,5'-Dibromo-3'-methyl-2'-nitro-1H,3'H-[2,4']biimidazolyl 

Relevant academic research and scientific papers

Synthesis method of 4-bromo-2-nitro-1H-imidazole

The invention provides a synthetic method of 4-bromine-2-nitro-1H-imidazole, relates to the field of medicinal chemistry, provides a new scheme for synthesizing 4-bromine-2-nitro-1H-imidazole by adopting 2-nitroimidazole through a three-step method, and provides a new synthetic route for preparation and synthesis of the 4-bromine-2-nitro-1H-imidazole. Moreover, in the synthesis scheme, common rawmaterials are adopted as reactants, the reaction conditions are proper, the total yield of the product is relatively high, the preparation process is relatively simple, the cost is low, large-scale production can be realized, and a synthesis idea is provided for synthesis of the derivative of the compound.

Synthesis and Reactions of Brominated 2-Nitroimidazoles

Various approaches to the synthesis of the hitherto-unknown 4(5)-bromo-2-nitroimidazole (5) are reported.Direct bromination of 2-nitroimidazole with N-bromosuccinimide gave the unreported 4,5-dibromo-2-nitroimidazole (10) in quantitative yield, but this could be selectively debrominated to give compound (5).While 1-methyl-2-nitroimidazole readily gave 4-bromo-1-methyl-2-nitroimidazole (15) on bromination, this could not be demethylated to give (5), and bromination of various other N-protected 2-nitroimidazoles was also unsuccessful.Lithiation of 4-bromo-1-tritylimidazole (21) followed by quenching with propyl nitrate gave (after detritylation and methylation) a mixture of a dimer (28) and compound (15), indicating that the desired product (5) is produced in this reaction although it can only be isolated in derivatized form.The proposed route for formation of the dimer suggests a general reaction between 1-alkyl-4-bromo-2-nitroimidazoles and strong C- and N-nucleophiles, resulting in substitution at the 5-position.