121816-84-0

Basic information

• Product Name: 4-BROMO-2-NITRO-1H-IMIDAZOLE
• Synonyms: 4-BROMO-2-NITRO-1H-IMIDAZOLE
• CAS NO: 121816-84-0
• Molecular Formula: C₃H₂BrN₃O₂
• Molecular Weight: 191.97088
• Product Categories: Imidazol&Benzimidazole
• Mol File: 121816-84-0.mol
• Article Data: 2

Chemical Properties

• Melting Point: >230 °C (decomp)
• Boiling Point: 427.802 °C at 760 mmHg
• Flash Point: 212.528 °C
• Appearance: /
• Density: 2.157 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.664
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 6.53±0.10(Predicted)
• CAS DataBase Reference: 4-BROMO-2-NITRO-1H-IMIDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BROMO-2-NITRO-1H-IMIDAZOLE(121816-84-0)
• EPA Substance Registry System: 4-BROMO-2-NITRO-1H-IMIDAZOLE(121816-84-0)

Safety Data

• Hazardous Substances Data: 121816-84-0(Hazardous Substances Data)

Usage

General Description

4-Bromo-2-nitro-1H-imidazole is a chemical compound with a formula of C3H2BrN3O2. Belonging to the class of organic compounds known as imidazoles, this chemical is recognized by specific nitro and bromo groups that are attached to its imidazole ring. It is frequently used within the scientific community for various chemical reactions and research due to its unique properties, including its high volatility and reactive nature. However, like many chemicals, it should be handled with care due to potential health risks if improperly handled or ingested. The exact behavior, usage, and potential risks remain the subject of various studies and depend significantly on the specific context and environment in which the chemical is used.

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 articles and documents

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.