16954-05-5

Basic information

• Product Name: 4,5-DIBROMO-1,2-DIMETHYL-1H-IMIDAZOLE
• Synonyms: 4,5-DIBROMO-1,2-DIMETHYL-1H-IMIDAZOLE;4,5-DIBROMO-1,2-DIMETHYLIMIDAZOLE;1,2-Dimethyl-4,5-dibromo-1H-imidazole;NSC 191261
• CAS NO: 16954-05-5
• Molecular Formula: C₅H₆Br₂N₂
• Molecular Weight: 253.92
• Product Categories: blocks;Bromides;Imidazoles
• Mol File: 16954-05-5.mol
• Article Data: 7

Chemical Properties

• Melting Point: 77-78°C
• Boiling Point: 331.3 °C at 760 mmHg
• Flash Point: 154.2 °C
• Appearance: /
• Density: 2.06 g/cm³
• Vapor Pressure: 0.000302mmHg at 25°C
• Refractive Index: 1.647
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 3.13±0.60(Predicted)
• CAS DataBase Reference: 4,5-DIBROMO-1,2-DIMETHYL-1H-IMIDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5-DIBROMO-1,2-DIMETHYL-1H-IMIDAZOLE(16954-05-5)
• EPA Substance Registry System: 4,5-DIBROMO-1,2-DIMETHYL-1H-IMIDAZOLE(16954-05-5)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 16954-05-5(Hazardous Substances Data)

Usage

General Description

4,5-DIBROMO-1,2-DIMETHYL-1H-IMIDAZOLE is a chemical compound that belongs to the imidazole class of chemicals. It is a white to light yellow solid with a molecular formula of C5H6Br2N2 and a molecular weight of 246.92 g/mol. 4,5-DIBROMO-1,2-DIMETHYL-1H-IMIDAZOLE is used as a reactive intermediate in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds. It is also used as a reagent in organic chemistry reactions, such as in the preparation of imidazole derivatives. However, it is important to handle this compound with care as it is a potential irritant to the skin, eyes, and respiratory system, and can cause harm if ingested or inhaled.

InChI:InChI=1/C5H6Br2N2/c1-3-8-4(6)5(7)9(3)2/h1-2H3

Upstream product

• 4002-81-7 4,5-Dibromo-2-methylimidazole 
• 77-78-1 dimethyl sulfate 
• 24021-93-0 (1,2-dimethyl-1H-imidazol-5-yl)methanol 
• 1739-84-0 1,2-dimethyl-1H-imidazole 

Relevant articles and documents

Convenient multi-gram scale synthesis of polybrominated imidazoles building blocks

The multi-gram scale polybromination of variously substituted imidazoles has been realized using a stoichiometric amount of the Br2-DMF complex. Good yields have been obtained compared to other methods using large amounts of acetic acid-sodium acetate buffer.

Imidazole-Fused Enediynes by Selective C5-C4 Alkynylations of 4,5-Dibromoimidazoles

An efficient synthesis of symmetrical 1,2-disubstituted 4,5-dialkynylimidazoles by Sonogashira alkynylation of the corresponding 4,5-dibromo derivatives was developed. Moreover, through a careful tuning of the palladium ligand, unsymmetrical 1,2-disusbtituted 4,5-dialkynylimidazoles were also prepared through a regioselective C5 alkynylation of 4,5-dibromoimidazoles, followed by a second alkynylation involving the 4-bromo derivatives so obtained. This interesting class of imidazole-fused enediynes is also able to give thermal Bergman cycloaromatization (BC), as proved by DSC experiments.

Synthesis, crystal structure and antibacterial activity of new highly functionalized ionic compounds based on the imidazole nucleus

Several new highly functionalized imidazolium derivatives were synthesized, via appropriate synthetic routes, using imidazole, 1-methylimidazole and 2-phenyl-1-methylimidazole as key intermediates. The antibacterial activity of the prepared compounds was evaluated against: Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa and Salmonella thipymurium using disk-diffusion and MIC methods. Crystal X-ray structures are reported for six compounds.