Production Method 1

58668-67-0

16567-18-3

81278-86-6

Reaction Conditions

1.1 Reagents: Aluminum bromide

Reference

Preparation of 3-substituted quinolines. II. Preparation and cyclodehydration of α-alkyl- and α-phenyl-β-arylaminoacrolein derivatives

Todoriki, Reiko; et al, Heterocycles, 1986, 24(3), 755-69

Production Method 2

4485-89-6

16567-18-3

81278-86-6

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Solvents: Chloroform
2.1 Reagents: Acetic acid ,  Sodium acetate Solvents: Water
3.1 Reagents: Aluminum bromide

Reference

Preparation of 3-substituted quinolines. II. Preparation and cyclodehydration of α-alkyl- and α-phenyl-β-arylaminoacrolein derivatives

Todoriki, Reiko; et al, Heterocycles, 1986, 24(3), 755-69

Production Method 3

16567-18-3

4964-71-0

81278-86-6

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Solvents: Dichloromethane

Reference

Bromination of quinolines by N-bromosuccinimide. Study of the isomeric composition of the bromination products by NMR and GLC methods

Tochilkin, A. I.; et al, Khimiya Geterotsiklicheskikh Soedinenii, 1988, (8), 1084-90

Production Method 4

25299-39-2

16567-18-3

81278-86-6

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Solvents: Chloroform
2.1 Reagents: Aluminum bromide

Reference

Preparation of 3-substituted quinolines. II. Preparation and cyclodehydration of α-alkyl- and α-phenyl-β-arylaminoacrolein derivatives

Todoriki, Reiko; et al, Heterocycles, 1986, 24(3), 755-69

Production Method 5

59360-06-4

16567-18-3

81278-86-6

Reaction Conditions

1.1 Reagents: Acetic acid ,  Sodium acetate Solvents: Water
2.1 Reagents: Aluminum bromide

Reference

Preparation of 3-substituted quinolines. II. Preparation and cyclodehydration of α-alkyl- and α-phenyl-β-arylaminoacrolein derivatives

Todoriki, Reiko; et al, Heterocycles, 1986, 24(3), 755-69

Production Method 6

122-31-6

16567-18-3

81278-86-6

Reaction Conditions

1.1 Reagents: Ethanol ,  Water
2.1 Reagents: N-Bromosuccinimide Solvents: Chloroform
3.1 Reagents: Acetic acid ,  Sodium acetate Solvents: Water
4.1 Reagents: Aluminum bromide

Reference

Preparation of 3-substituted quinolines. II. Preparation and cyclodehydration of α-alkyl- and α-phenyl-β-arylaminoacrolein derivatives

Todoriki, Reiko; et al, Heterocycles, 1986, 24(3), 755-69

8-Bromoquinoline Raw materials

• N-(3-Anilino-2-propenylidene)aniline
• 1,1,3,3-Tetraethoxypropane
• 2-Propenal,3-(phenylamino)-
• BENZENAMINE, N-[2-BROMO-3-(PHENYLAMINO)-2-PROPENYLIDENE]-
• 2-PROPENAL, 2-BROMO-3-(PHENYLAMINO)-

8-Bromoquinoline Preparation Products

• 8-Bromoquinoline (16567-18-3)
• 5-Bromoquinoline (4964-71-0)
• 5,8-Dibromoquinoline (81278-86-6)

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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Quinolines and derivatives Haloquinolines

8-Bromoquinoline (CAS No. 16567-18-3): A Versatile Intermediate in Modern Chemical Biology and Medicinal Chemistry

8-Bromoquinoline, with the chemical formula C?H?BrN? and CAS number 16567-18-3, is a brominated derivative of quinoline. This heterocyclic compound has garnered significant attention in the fields of chemical biology and medicinal chemistry due to its versatile structural framework, which serves as a crucial intermediate in the synthesis of various pharmacologically active molecules. The presence of both a bromine substituent and a quinoline core provides unique reactivity, making it an invaluable building block for drug discovery and material science applications.

The quinoline scaffold, a fused bicyclic system consisting of a benzene ring and a pyridine ring, has a long history in pharmaceutical development. Quinoline derivatives have been instrumental in the treatment of diseases such as malaria, with compounds like chloroquine and primaquine being well-documented examples. The introduction of a bromine atom at the 8-position of the quinoline ring enhances its utility by introducing electrophilic aromatic substitution sites, facilitating further functionalization through cross-coupling reactions, nucleophilic substitutions, and other synthetic transformations.

In recent years, 8-Bromoquinoline has found extensive use in the development of small-molecule inhibitors targeting various biological pathways. One notable area of research involves its application in anticancer drug design. The quinoline moiety is known to interact with DNA and proteins, making it an effective scaffold for developing agents that modulate critical cellular processes. For instance, studies have demonstrated the potential of 8-bromoquinoline derivatives as kinase inhibitors, particularly those targeting tyrosine kinases involved in cancer cell proliferation and survival. The bromine atom at the 8-position allows for facile introduction of additional functional groups, enabling fine-tuning of binding affinity and selectivity.

Moreover, 8-Bromoquinoline has been explored in the synthesis of antiviral agents. The quinoline core exhibits broad-spectrum antiviral activity by interfering with viral replication cycles. Researchers have leveraged the reactivity of the 8-bromo derivative to develop novel antiviral compounds targeting RNA viruses, including those responsible for influenza and hepatitis C. The ability to modify the quinoline structure through bromine-mediated reactions has led to the discovery of several lead compounds with promising antiviral properties.

The compound's significance extends beyond pharmaceutical applications into materials science. Quinoline derivatives are known for their ability to form coordination complexes with metal ions, which has led to their exploration as luminescent materials and catalysts. Specifically, complexes formed between 8-bromoquinoline and transition metals such as copper and zinc have shown promise in optoelectronic devices due to their emission properties. These findings highlight the compound's potential in developing advanced materials for sensors and light-emitting technologies.

Recent advancements in synthetic methodologies have further enhanced the utility of 8-Bromoquinoline. Transition-metal-catalyzed cross-coupling reactions, particularly palladium-catalyzed Suzuki-Miyaura and Heck couplings, have enabled the efficient construction of complex quinoline derivatives from 8-bromoquinoline precursors. These techniques have been instrumental in generating libraries of novel compounds for high-throughput screening, accelerating the discovery process in drug development.

The incorporation of computational chemistry techniques has also played a pivotal role in optimizing derivatives of 8-bromoquinoline for therapeutic applications. Molecular modeling studies have helped elucidate binding interactions between quinoline-based compounds and biological targets, providing insights into structure-activity relationships. This computational approach has guided synthetic efforts toward designing more potent and selective agents with improved pharmacokinetic profiles.

In conclusion, 8-Bromoquinoline (CAS No. 16567-18-3) represents a cornerstone molecule in modern chemical biology and medicinal chemistry. Its unique structural features enable diverse synthetic manipulations, making it an indispensable tool for developing innovative therapeutics across multiple disease areas. As research continues to uncover new applications for this versatile intermediate, its importance is poised to grow further, driving advancements in both academic research and industrial drug development pipelines.

• 51417-51-7(7-Bromo-1H-indole)
• 5332-24-1(3-Bromoquinoline)
• 1070879-31-0(4,8-Dibromoquinoline)
• 69268-39-9(3,6-Dibromoquinoline)
• 90224-68-3(Quinoline, 3-bromo-, hydrochloride)
• 17965-74-1(8-Bromo-1,6-naphthyridine)
• 650583-75-8(6,8-Dibromo-quinoline)
• 17965-75-2(3,8-Dibromo-1,6-naphthyridine)
• 81278-86-6(5,8-Dibromoquinoline)
• 1081803-09-9(8-Bromoquinoline hydrochloride)