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

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

Uses

Used in Pharmaceutical Industry:
4,5-DIBROMO-1,2-DIMETHYL-1H-IMIDAZOLE is used as a reactive intermediate for the synthesis of pharmaceuticals. It plays a crucial role in the development of new drugs, contributing to the creation of a wide range of medicinal compounds.
Used in Agrochemical Industry:
In the agrochemical sector, 4,5-DIBROMO-1,2-DIMETHYL-1H-IMIDAZOLE is utilized as a reactive intermediate in the production of agrochemicals. Its involvement in the synthesis of various agrochemicals aids in enhancing crop protection and productivity.
Used in Organic Chemistry:
4,5-DIBROMO-1,2-DIMETHYL-1H-IMIDAZOLE also serves as a reagent in organic chemistry reactions. It is particularly instrumental in the preparation of imidazole derivatives, which are important building blocks for a variety of organic compounds.
Safety Precautions:
It is important to handle 4,5-DIBROMO-1,2-DIMETHYL-1H-IMIDAZOLE with care due to its potential irritant properties. It can cause harm to the skin, eyes, and respiratory system, and poses a risk if ingested or inhaled. Proper safety measures should be taken to minimize exposure and ensure the safe use of 4,5-DIBROMO-1,2-DIMETHYL-1H-IMIDAZOLE in various applications.

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.

Asymmetric synthesis and biological evaluation of imidazole- and oxazole-containing synthetic lipoxin A4 mimetics (sLXms)

Lipoxins (LXs) are endogenously generated eicosanoids with potent bio-actions consistent with attenuation of inflammation. The costly synthesis and metabolic instability of LXs may limit their therapeutic potential. Here we report the synthesis and charac

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.

HETEROCYCLIC LIPXON ANALOGS AND USES THEROF

The present invention relates to a compound of formula (I): wherein L is an optionally substituted heterocyclic group excluding unsubstituted monocyclic pyridine groups; wherein a is 0, 1 or 2; wherein R1 is H or with R2 is a bond; wherein R2 is an optionally substituted alkoxy or aryloxy group, or with R1 forms a bond; wherein R3 is an optionally substituted alkyl group; and wherein R4 is CH2, CMe2 or O. Such compounds may be used in the treatment or prophylaxis of a disease or condition in which inhibition of acute inflammation and/or promotion of its resolution and/or suppression of fibrosis.

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.

Development of an efficient process towards the benzimidazole BYK308944: A key intermediate in the synthesis of a potassium-competitive acid blocker

An entirely new synthesis of the important benzimidazole building block BYK308944 was elaborated using the Stobbe reaction as central element. BYK308944 constitutes an important intermediate for the preparation of 3,6,7,8-tetrahydrochromeno[7,8-d] imidazoles as potassium-competitive acid blockers. The new route relies on the hydroxymethylation of 1,2- dimethylimidazole as cheap starting material followed by oxidation of the corresponding alcohol and Stobbe condensation of the resulting aldehyde with diethyl succinate. All synthetic steps of this new approach were optimized particularly with the goal to establish a process amenable for large- scale preparation.

Reactions of 1,2-Dimethylimidazole, Particularly its Metallation

A re-examination of the metallation of 1,2-dimethylimidazole has shown that, after quenching of reaction mixtures with suitable reagents, single products may arise from substitution either in the 2-methyl group or in the 5-position or mixtures of both products may arise, depending on the metallating reagent, solvent, and reaction conditions. 1,2-Dimethylimidazol-5-yl-lithium was prepared by reaction of 1,2-dimethyl-5-trimethylstannylimidazole (13) with n-butyl-lithium in tetrahydrofuran at -100 deg C.The corresponding 5-trimethylsilyl compounds (12) was metallated by n-butyl-lithium exclusively in the 2-methyl group. 1,2-Dimethylimidazol-5-yl-lithium was shown to undergo transmetallation reactions at temperatures higher than -100 deg C.An improved procedure is given for the synthesis of 1,2-dimethylimidazole-5-carbaldehyde via hydroxymethylation of 1,2-dimethylimidazole and oxidation of the 5-hydroxymethyl group with nitric acid.