2302-30-9

Basic information

• Product Name: 4,5-Dibromo-1H-imidazole
• Synonyms: 4,5-dibromo-1h-imidazol;4,5-dibromoimidazole;4,5-DIBROMO-1H-IMIDAZOLE;4,5-Dibromo-1H-imidazole98%
• CAS NO: 2302-30-9
• Molecular Formula: C₃H₂Br₂N₂
• Molecular Weight: 225.87
• EINECS: 200-258-5
• Product Categories: blocks;Bromides;Imidazoles;Imidaxoles
• Mol File: 2302-30-9.mol
• Article Data: 3

Chemical Properties

• Melting Point: 214-216°C
• Boiling Point: 388.6°Cat760mmHg
• Flash Point: 188.8°C
• Appearance: /
• Density: 2.419
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.607
• Storage Temp.: Keep Cold
• PKA: 8.99±0.10(Predicted)
• CAS DataBase Reference: 4,5-Dibromo-1H-imidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5-Dibromo-1H-imidazole(2302-30-9)
• EPA Substance Registry System: 4,5-Dibromo-1H-imidazole(2302-30-9)

Safety Data

• Hazard Codes: Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 2302-30-9(Hazardous Substances Data)

Usage

General Description

4,5-Dibromo-1H-imidazole is a chemical compound with the molecular formula C3H3Br2N2. It is a heterocyclic organic compound that contains both bromine and nitrogen atoms. 4,5-Dibromo-1H-imidazole is mainly used in the pharmaceutical and agricultural industries as a building block for the synthesis of various pharmaceuticals, pesticides, and other biologically active compounds. It is known for its antimicrobial and antifungal properties, making it a valuable ingredient in the development of new medicines and agricultural products. Additionally, 4,5-Dibromo-1H-imidazole is also used as a reagent in organic synthesis and as a precursor for the preparation of other chemical compounds. However, it is important to handle this chemical with care, as it may be harmful if ingested, inhaled, or in contact with the skin.

InChI:InChI=1/C11H8BrNO/c12-9-6-11(8-13-7-9)14-10-4-2-1-3-5-10/h1-8H

Upstream product

• 288-32-4 1H-imidazole 
• 67-66-3 chloroform 
• 7726-95-6 bromine 
• 2034-22-2 2,4,5-tribromo-1H-imidazole 
• 7732-18-5 water 

Downstream Products

• 1003-50-5 4,5-dibromo-1-methyl-1H-imidazole 
• 2302-25-2 4-bromo-1 H-imidazole 
• 106848-48-0 4-bromoimidazol-5-yldiphenylmethanol 
• 106848-48-0 5-bromoimidazol-4-yldiphenylmethanol 
• 112517-23-4 4,5-dibromo-1-tritylimidazole 
• 112517-27-8 4,5-dibromo-1-phenylsulphonylimidazole 
• 112517-28-9 4,5-dibromo-1-(4-tolylsulphonyl)imidazole 
• 1346263-45-3 4,5-dibromo-2-(phenylazo)imidazole 

Relevant articles and documents

Peroxo–tungstate(VI) complexes: syntheses, characterization, reactivity, and DFT studies

Abstract: Three new oxodiperoxo–tungsten(VI) complexes containing benzene core carboxylic acids, viz., benzoic acid, 2-chlorobenzoic acid, and 3-aminobenzoic acid as co-ligands have been synthesized from reaction of Na2WO6H4, 30% H2O2 and the corresponding co-ligands in aqueous medium. The compounds have been comprehensively characterized by elemental analyses, FT-IR, 1H NMR, UV–Vis spectral studies as well as by mass spectrometric and TGA analyses. The infrared spectra suggest occurrence of terminally bonded W=O as well as triangular bidentate peroxo groups (C2v) and monodentate carboxylate group bound to the WO4+ center. The mass spectra of the compounds are in good agreement with proposed molecular formulations. Thermogravimetric analyses indicate the existence of both lattice and coordinated water molecules in the complexes. Density functional theory (DFT) calculations were used to compute the frequencies of relevant vibrational modes, electronic properties and also to investigate structure of the compounds. Compound potassium(aquo)(2-chlorobenzoato)oxodiperoxo–tungstate(VI)dihydrate acts as an oxidant for bromide ion in aqueous phase bromination of chosen organic substrates to their corresponding bromo-organics. Graphical abstract: [Figure not available: see fulltext.]

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.