Home Chemistry Heterocyclic Building Blocks Pyridines 3-Bromo-5-Nitropyridine
Substitution Reactions: The bromine atom in the 3-position can undergo nucleophilic substitution reactions, where it is replaced by another nucleophile. For instance, in an SN2 reaction, the bromine atom can be replaced by a nucleophile such as an alkoxide ion or an amine.
Nitration: The nitro group is electron-withdrawing, making the aromatic ring susceptible to electrophilic aromatic substitution reactions. In a nitration reaction, the nitro group can be further substituted with a nitro group in the presence of a nitrating agent like nitric acid.
Reduction: The nitro group can be reduced to an amino group under appropriate conditions, such as using reducing agents like iron and hydrochloric acid (Fe/HCl), tin and hydrochloric acid (Sn/HCl), or catalytic hydrogenation.
Metalation: The pyridine ring can undergo metalation reactions, where a metal atom replaces one of the hydrogen atoms on the aromatic ring. This metalated intermediate can then be used in various cross-coupling reactions or other transformations.
Suzuki Coupling: 3-bromo-5-nitropyridine can participate in Suzuki coupling reactions where it undergoes a cross-coupling reaction with an organoboron compound in the presence of a palladium catalyst to form a new carbon-carbon bond.
Sonogashira Coupling: It can also undergo Sonogashira coupling reactions, where it reacts with an alkynyl group in the presence of a palladium catalyst and a copper salt to form a new carbon-carbon bond.
Heterocyclic Chemistry: Being a substituted pyridine derivative, it can participate in various heterocyclic chemistry reactions, including cyclization reactions to form fused ring systems or other heterocycles.
Functional Group Transformations: The nitro and bromo groups can be used as handles for further functionalization through various synthetic transformations, such as reduction, oxidation, and substitution reactions.
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1-(5-Bromo-3-nitropyridin-2-yl)ethanone
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Methyl 2-(5-bromo-3-nitropyridin-2-yl)acetate
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Ethyl 2-(5-bromo-3-nitropyridin-2-yl)acetate
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