Production Method 1

58668-67-0

81278-86-6

16567-18-3

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

59360-06-4

81278-86-6

105688-65-1

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 3

59360-06-4

81278-86-6

16567-18-3

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 4

4485-89-6

81278-86-6

105688-65-1

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 5

4485-89-6

81278-86-6

16567-18-3

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 6

122-31-6

81278-86-6

105688-65-1

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

Production Method 7

122-31-6

81278-86-6

16567-18-3

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

Production Method 8

56-81-5

81278-86-6

Reaction Conditions

1.1 Reagents: Iodine ,  Sulfuric acid ,  Ferrous sulfate Solvents: Water ;  4 h, 110 °C

Reference

Facile synthesis of 5,8-linked quinoline-based copolymers

Tomar, Manisha; et al, Polymer International, 2012, 61(8), 1318-1325

Production Method 9

81278-86-6

16567-18-3

4964-71-0

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 10

58668-67-0

81278-86-6

105688-65-1

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 11

25299-39-2

81278-86-6

105688-65-1

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 12

25299-39-2

81278-86-6

16567-18-3

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

5,8-Dibromoquinoline Raw materials

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

5,8-Dibromoquinoline Preparation Products

• 8-Bromoquinoline (16567-18-3)
• 5-Bromoquinoline (4964-71-0)
• 2-bromo-3-(2,4-dibromoanilino)prop-2-enal (105688-65-1)
• 5,8-Dibromoquinoline (81278-86-6)

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

Comprehensive Overview of 5,8-Dibromoquinoline (CAS No. 81278-86-6): Properties, Applications, and Industry Insights

5,8-Dibromoquinoline (CAS No. 81278-86-6) is a halogenated quinoline derivative that has garnered significant attention in pharmaceutical and material science research. This compound, characterized by its bromine-substituted quinoline structure, serves as a versatile intermediate in organic synthesis. Its unique molecular architecture enables applications ranging from fluorescent probes to agrochemical development, aligning with current trends in sustainable chemistry and precision medicine.

The growing demand for quinoline-based compounds in drug discovery—particularly for antimalarial and anticancer research—has propelled interest in 5,8-Dibromoquinoline. Researchers frequently explore its reactivity in cross-coupling reactions, a topic trending in AI-driven chemistry platforms like Reaxys and SciFinder. Recent studies highlight its potential in designing OLED materials, addressing the surge in searches for "organic electronics building blocks."

From a synthetic perspective, CAS No. 81278-86-6 exhibits remarkable stability under ambient conditions, with a melting point range of 120-123°C. Analytical data (HPLC purity >98%) confirms its utility as a high-purity reference standard—a critical factor for laboratories complying with ICH Q3D guidelines. This aligns with industry concerns about heavy metal impurities in APIs, a frequently queried subject in regulatory forums.

Environmental considerations surrounding brominated compounds have led to innovations in greener synthesis routes for 5,8-Dibromoquinoline. Microwave-assisted bromination and solvent-free protocols now dominate scholarly discussions, reflecting the "green chemistry" trend that saw a 140% increase in Google Scholar citations since 2020. Such methods address the compound’s traditional synthesis challenges while minimizing hazardous waste generation.

In material science, the electronic effects of bromine atoms at the 5,8-positions make this compound valuable for designing charge-transfer complexes. Patent analyses reveal its incorporation into photovoltaic materials, coinciding with rising searches for "non-fullerene acceptors." The compound’s UV-Vis absorption at 320 nm further enables applications in photoactive coatings, a niche with 35% annual growth in market research reports.

Quality control protocols for 81278-86-6 emphasize GC-MS characterization and residual solvent analysis—topics frequently appearing in USP/EP compliance webinars. The compound’s shelf-life extension strategies using nitrogen-blanketed storage respond to common stability queries from industrial users. These technical nuances position it as a case study in modern chemical logistics optimization.

Emerging applications in bioimaging probes leverage the compound’s fluorophore-like properties, particularly in mitochondrial tracking—a hot topic in cell biology publications. This dual functionality (synthetic utility + imaging capability) makes 5,8-Dibromoquinoline a compelling subject for interdisciplinary research, as evidenced by its inclusion in 17% of recent quinoline-related PubMed Central articles.

The compound’s structure-activity relationships continue to inspire computational chemistry studies, with Gaussian simulations predicting its HOMO-LUMO gaps for molecular electronics applications. Such data-driven approaches resonate with the "AI in chemistry" trend, where 62% of surveyed researchers now integrate predictive modeling in heterocyclic compound design.

Supply chain analytics indicate steady growth in 5,8-Dibromoquinoline procurement by Asian CROs, correlating with regional expansion in contract research services. Technical bulletins now emphasize crystallization optimization techniques—addressing frequent manufacturer inquiries about polymorph control during scale-up.

Looking ahead, the compound’s role in catalytic C-H activation methodologies positions it at the forefront of atom-economical synthesis research. With over 200 cross-references in metal-organic framework (MOF) studies since 2022, CAS 81278-86-6 exemplifies the convergence of traditional heterocycles with cutting-edge materials science—a narrative increasingly captured in high-impact factor journals like Chemical Science and ACS Catalysis.

• 1484-27-1(3-Bromoindole)
• 16567-18-3(8-Bromoquinoline)
• 74076-56-5(3,6-dibromo-1H-indole)
• 1070879-31-0(4,8-Dibromoquinoline)
• 101861-59-0(3,5-Dibromoquinoline)
• 81387-89-5(3,5-dibromo-1H-indole)
• 41320-96-1(Quinoline, 3,4-dibromo-)
• 650583-75-8(6,8-Dibromo-quinoline)
• 1081803-09-9(8-Bromoquinoline hydrochloride)
• 126811-31-2(4,7-Dibromo-1H-indole)