16265-11-5

Basic information

• Product Name: 4-Bromo-2-methylimidazole
• Synonyms: 4-BROMO-2-METHYLIMIDAZOLE;4-Bromo-2-methyl-1H-imidazole;4-Bromo-2-methyl-1H-imidazole 98%;2-Methyl-4-bromo-1H-imidazole;5-BroMo-2-Methyl-1H-iMidazole
• CAS NO: 16265-11-5
• Molecular Formula: C₄H₅BrN₂
• Molecular Weight: 161
• Product Categories: blocks;Bromides;Imidazoles;Imidazol&Benzimidazole;Imidaxoles
• Mol File: 16265-11-5.mol
• Article Data: 3

Chemical Properties

• Melting Point: 158-160°C
• Boiling Point: 333.9°Cat760mmHg
• Flash Point: 155.7°C
• Appearance: /
• Density: 1.723g/cm³
• Vapor Pressure: 0.000257mmHg at 25°C
• Refractive Index: 1.584
• Storage Temp.: Keep Cold
• PKA: 12.26±0.10(Predicted)
• CAS DataBase Reference: 4-Bromo-2-methylimidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromo-2-methylimidazole(16265-11-5)
• EPA Substance Registry System: 4-Bromo-2-methylimidazole(16265-11-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 16265-11-5(Hazardous Substances Data)

Usage

General Description

4-Bromo-2-methylimidazole is a chemical compound with the molecular formula C4H5BrN2. It is a white crystalline solid that is commonly used in organic synthesis and pharmaceutical research. 4-Bromo-2-methylimidazole is a derivative of imidazole, a five-membered heterocyclic ring containing two nitrogen atoms. 4-Bromo-2-methylimidazole is known for its reactivity and is often used as a building block in the synthesis of various pharmaceuticals and agrochemicals. It is also used in the production of dyes and other specialty chemicals. 4-Bromo-2-methylimidazole has a wide range of applications in the chemical and pharmaceutical industries due to its versatile chemical properties.

InChI:InChI=1/C4H5BrN2/c1-3-6-2-4(5)7-3/h2H,1H3,(H,6,7)

Upstream product

• 4002-81-7 4,5-Dibromo-2-methylimidazole 
• 693-98-1 2-methylimidazole 

Downstream Products

• 24134-09-6 5-bromo-1,2-dimethyl-1H-imidazole 
• 850429-59-3 4-bromo-1,2-dimethyl-1H-imidazole 
• 1135683-20-3 C₁₂H₁₁BrN₂O₃ 
• 13739-48-5 2-methyl-4-phenyl-1H-imidazole 

Relevant articles and documents

Some contribution to W(VI)-peroxo-chemistry: Synthesis, spectroscopic characterization, reactivity and DFT studies

Synthesis of white microcrystalline oxodiperoxotungstate(VI) complexes, K[WO(O2)2(L)(H2O)]·H2O, (L ?= ?salicylate, 5-chlorosalicylate, 4-hydroxybenzoate) have been achieved from reaction of Na2WO4·2H2O with 30% H2O2 and the respective hetero-ligands at pH Ca. 7–7.5 in aqueous medium. The newly synthesized compounds were comprehensively characterized by elemental analyses, spectral studies, room temperature magnetic moment measurements and mass spectrometric studies. Infrared spectra suggest that, peroxo groups are bonded to the WO+4 center in a triangular bidentate (C2v) fashion and the hetero-ligands benzene-core hydroxycarboxylic acids viz. salicylic acid, 5-chlorosalicylic acid, 4-hydroxybenzoic acid in anoinic form are coordinated in monodentate manner. Compounds are fairly stable in aqueous solution for sufficient period of time. The results of mass spectrometric analysis lend support to the molecular composition of the complexes ascertained on the basis of elemental analyses and spectroscopic studies. Compound potassium(aquo)(5-chlorosalicylato)oxodiperoxotungstate(VI)monohydrate, K[WO(O2)2(5-chlorosalicylate)(H2O)]·H2O, act as an oxidant of bromide ion in aqueous phase bromination of chosen organic substrates to their corresponding bromo organics. Density Functional Theory (TD-DFT) calculations were performed on the synthesized complexes substantiated the experimentally obtained results. The TD-DFT optimized structures are in excellent agreement with the results of elemental analyses, spectral as well as mass spectrometric data.

Highly regioselective C-5 alkynylation of imidazoles by one-pot sequential bromination and Sonogashira cross coupling

A variety of 2-substituted 5-alkynyl-1H-imidazoles were easily prepared by a one-pot sequential procedure involving a highly regioselective electrophilic C-5 bromination of 1,2-dimethyl-1H-imidazole, 2-chloro-1-methyl-1H-imidazole, and 2-aryl-1-methyl-1H-imidazoles, followed by an efficient palladium/copper co-catalyzed Sonogashira-type alkynylation.