• 1. 373. Cinnolines. Part XXXI. The nature of the C(3)-position. Some experiments with 3-substituted cinnolines
  E. J. Alford,K. Schofield J. Chem. Soc. 1953 1811
• 2. 85. Cinnolines. Part XXV. Experiments with 3-halogeno-4-hydroxycinnolines. Some halogen exchange reactions
  K. Schofield,T. Swain J. Chem. Soc. 1950 384
• 3. Tautomeric azines. Part V. Cinnolin-3(2H)-one and 3- and 4-aminocinnoline
  A. J. Boulton,I. J. Fletcher,A. R. Katritzky J. Chem. Soc. B 1971 2344
• 4. 86. Cinnolines. Part XXVI. Some 4-cinnolylhydrazines, their preparation and oxidation. Miscellaneous quinoline derivatives
  K. Schofield,T. Swain J. Chem. Soc. 1950 392
• 5. 123. Cinnolines. Part XXX. The nature of the C(3)-position. The synthesis of 3-methyl-, 3-chloro-, and 3-bromo-cinnoline; also, of cinnoline and the Bz-nitrocinnolines
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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Diazanaphthalenes Cinnolines
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Diazanaphthalenes Benzodiazines Cinnolines

3-Bromocinnoline: A Comprehensive Overview

3-Bromocinnoline, also known as 3-bromo-1H-cinnoline, is a heterocyclic aromatic compound with the CAS number 78593-33-6. This compound belongs to the cinnoline family, which is a class of bicyclic aromatic heterocycles consisting of two fused rings: a benzene ring and a pyridazine ring. The presence of a bromine atom at the 3-position of the cinnoline framework introduces unique chemical and physical properties, making it an interesting molecule for various applications in organic synthesis, materials science, and drug discovery.

The molecular formula of 3-Bromocinnoline is C9H6BrN2, and its molecular weight is approximately 205.04 g/mol. It exists as a crystalline solid under standard conditions and is sparingly soluble in water but exhibits good solubility in organic solvents such as dichloromethane, chloroform, and ethanol. The compound is stable under normal conditions but may undergo decomposition under harsh acidic or basic conditions or when exposed to strong oxidizing agents.

3-Bromocinnoline has been extensively studied due to its potential as a building block in organic synthesis. Its structure allows for various substitution reactions, making it a valuable intermediate in the construction of more complex molecules. Recent research has focused on its use in the synthesis of heterocyclic compounds with potential applications in pharmaceuticals and agrochemicals.

In terms of synthesis, 3-Bromocinnoline can be prepared via several methods. One common approach involves the bromination of cinnoline using bromine in a suitable solvent such as acetic acid or sulfuric acid. Another method involves the condensation of o-aminophenol derivatives with aldehydes or ketones in the presence of an acid catalyst. These methods have been optimized to improve yield and purity, making them suitable for large-scale production.

The application of 3-Bromocinnoline extends beyond organic synthesis. Recent studies have explored its role as a ligand in transition metal catalysis, where it has shown promise in facilitating various coupling reactions. Additionally, its photochemical properties have been investigated for potential use in optoelectronic materials such as organic light-emitting diodes (OLEDs) and photovoltaic devices.

In the field of pharmacology, 3-Bromocinnoline has been evaluated for its potential as an anticancer agent. Preclinical studies have demonstrated that certain derivatives exhibit cytotoxic activity against various cancer cell lines. The compound's ability to modulate key cellular pathways makes it a candidate for further exploration in drug development.

The unique electronic properties of 3-Bromocinnoline also make it an attractive candidate for use in coordination chemistry. Researchers have reported the formation of metal complexes with transition metals such as copper, iron, and zinc. These complexes exhibit interesting magnetic and optical properties, which could be harnessed for applications in sensing and imaging technologies.

In conclusion, 3-Bromocinnoline is a versatile compound with a wide range of applications across multiple disciplines. Its chemical stability, reactivity, and unique properties continue to make it an area of active research interest. As new synthetic methods and applications emerge, this compound is poised to play an increasingly important role in both academic and industrial settings.

• 40598-76-3(3,5-Dibromo-1H-indazole)
• 887568-41-4(3,4,6-Tribromo (1H)indazole)
• 1083181-45-6(3-Bromo-7-chlorocinnoline)
• 75608-85-4(Cinnoline, 3,4-dibromo-)
• 3660-90-0(1,4-Dibromophthalazine)
• 40598-94-5(3-Bromo-1H-indazole)
• 40598-72-9(3-bromo-5-methyl-2H-indazole)
• 3660-91-1(1-bromophthalazine)
• 885521-84-6(3,6-Dibromo (1h)Indazole)
• 885521-68-6(3,4-Dibromo (1H)indazole)