15862-30-3

Usage

Uses

Used in Pharmaceutical Industry:
3-Bromo-5-nitropyridine is used as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of biologically active molecules. Its unique structure allows for the creation of diverse drug candidates that can address various medical needs.
Used in Agrochemical Industry:
In the agrochemical sector, 3-Bromo-5-nitropyridine is utilized as an intermediate in the production of compounds that can protect crops from pests and diseases, thereby enhancing agricultural productivity.
Used in Organic Chemistry Research:
3-Bromo-5-nitropyridine is employed as a building block and reagent in organic chemistry reactions, facilitating the preparation of heterocyclic compounds and contributing to the advancement of chemical research.
Used in Material Science:
3-BROMO-5-NITROPYRIDINE is also used in the development of new materials, where its properties can be leveraged to create innovative substances with unique characteristics for various applications.

InChI:InChI=1/C5H3BrN2O2/c6-4-1-5(8(9)10)3-7-2-4/h1-3H

Upstream product

• 626-55-1 3-Bromopyridine 
• 15862-42-7 5-bromo-2-hydrazino-3-nitropyridine 
• 67443-38-3 5-bromo-2-chloro-3-nitropyridine 
• 452972-13-3 2-[(5-bromo)pyridin-3-yl]-4,4',5,5'-tetramethyl-1,3-dioxaborolane 

Downstream Products

• 13535-01-8 3-amino-5-bromopyridine 
• 462-08-8 pyridin-3-ylamine 
• 87883-17-8 3-acetyl-5-nitropyridine 
• 1073354-99-0 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-3-ylamine 
• 1428065-77-3 3-nitro-5-phenylmethylpyridine 

Relevant academic research and scientific papers

Reactions of 3-R-5-nitropyridines with nucleophiles: Nucleophilic substitution vs conjugate addition

A number of 3-R-5-nitropyridines were synthesized and their reactions with various types of nucleophiles were investigated. The reaction outcome depends on the nature of a nucleophile: in case of anionic O-, N- and S-nucleophiles the previously unreported substitution of non-activated nitro group occurred while carbon nucleophiles underwent dearomatization of the pyridine ring with the formation of products of 1,2- and 1,4-addition.

meta-Nitration of Arenes Bearing ortho/para Directing Group(s) Using C?H Borylation

Herein, we report the meta-nitration of arenes bearing ortho/para directing group(s) using the iridium-catalyzed C?H borylation reaction followed by a newly developed copper(II)-catalyzed transformation of the crude aryl pinacol boronate esters into the corresponding nitroarenes in a one-pot fashion. This protocol allows the synthesis of meta-nitrated arenes that are tedious to prepare or require multistep synthesis using the existing methods. The reaction tolerates a wide array of ortho/para-directing groups, such as ?F, ?Cl, ?Br, ?CH3, ?Et, ?iPr ?OCH3, and ?OCF3. It also provides regioselective access to the nitro derivatives of π-electron-deficient heterocycles, such as pyridine and quinoline derivatives. The application of this method is demonstrated in the late-stage modification of complex molecules and also in the gram-scale preparation of an intermediate en route to the FDA-approved drug Nilotinib. Finally, we have shown that the nitro product obtained by this strategy can also be directly converted to the aniline or hindered amine through Baran's amination protocol.