1133115-78-2 | 5-Bromo-8-fluoroquinoline

CAS:1133115-78-2 | 5-Bromo-8-fluoroquinoline,Description

5-Bromo-8-fluoroquinoline is a heterocyclic compound that contains a quinoline ring with a fluorine and bromine atom substitution at the 8th and 5th position, respectively. It is a solid substance with a molecular weight of 226.05.

Synthesis Analysis

The synthesis of 8-bromo-5-fluoroquinoline involves a two-stage process. In the first stage, 2-bromo-5-fluoroaniline reacts with glycerol in the presence of sulfuric acid and sodium 3-nitrobenzenesulfonate in water at 60 - 130°C for 3 hours. In the second stage, the product from the first stage reacts with sodium hydroxide in tert-butyl methyl ether and water. The yield of this synthesis process is approximately 89.8%.

Molecular Structure Analysis

The molecular formula of 5-Bromo-8-fluoroquinoline is C9H5BrFN. The InChI code is 1S/C9H5BrFN/c10-7-3-4-8(11)9-6(7)2-1-5-12-9/h1-5H and the SMILES string is FC1=CC=C(C2=CC=CN=C12)Br.

Physical And Chemical Properties Analysis

5-Bromo-8-fluoroquinoline is a solid substance with a molecular weight of 226.04 g/mol. It has a topological polar surface area of 12.9 Ų and a complexity of 165. The compound has no hydrogen bond donors but has two hydrogen bond acceptors.

Scientific Research Applications

Synthesis and Biological Activities

5-Bromo-8-fluoroquinoline derivatives serve as versatile building blocks in organic synthesis, particularly for creating various quinoline systems. For instance, these derivatives have been utilized to synthesize thieno[3,2-c]quinoline, pyrrolo[3,2-c]quinoline, and N-methylpyrrolo[3,2-c]quinoline systems. Notably, these compounds exhibit significant antibacterial activity against both gram-positive and gram-negative bacterial strains. Furthermore, certain derivatives have demonstrated remarkable antifungal properties, highlighting their potential in developing new antimicrobial agents (Abdel‐Wadood et al., 2014) .

Metalation and Functionalization

5-Bromo-8-fluoroquinoline derivatives have been shown to be amenable to metalation and functionalization processes. These procedures enable the introduction of various functional groups, offering a pathway to synthesize diverse quinoline derivatives with potential applications in pharmaceuticals and material science (Ondi et al., 2005).

Key Intermediate in Drug Discoveries

In drug discovery and development, 5-Bromo-8-fluoroquinoline derivatives have been identified as key intermediates. For example, the compound 5-bromo-2-methylamino-8-methoxyquinazoline, derived from 5-Bromo-8-fluoroquinoline, has been synthesized more efficiently by reducing isolation processes. This improvement in the synthesis process enhances the supply of these compounds for medicinal research (Nishimura & Saitoh, 2016).

Photoluminescence Properties

8-Hydroxyquinoline derivatives, including those with bromo-fluoro substitutions, have been studied for their photoluminescence properties. The luminescence wavelength of these derivatives tends to shift towards red compared to 8-hydroxyquinoline. This characteristic is significant in the development of materials with specific optical properties, which can be used in various applications, including sensors and display technologies (Xinhua et al., 2007).

Safety And Hazards

The safety data sheet for 5-Bromo-8-fluoroquinoline indicates that it is classified under GHS07 and has a hazard classification of Acute Tox. 4 Oral. Precautionary measures include avoiding dust formation, avoiding breathing mist, gas or vapours, avoiding contact with skin and eye, and using personal protective equipment.

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