96424-68-9

Usage

Uses

Used in Pharmaceutical Industry:
2-Bromo-3-chloropyridine is used as a key intermediate for the synthesis of various pharmaceuticals. Its ability to act as a halogenating agent makes it valuable in the development of new drugs with specific therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical sector, 2-Bromo-3-chloropyridine is utilized as a precursor in the production of herbicides and insecticides. Its reactivity allows for the creation of compounds that can effectively control pests and weeds in agricultural settings.
Used in Organic Synthesis:
2-Bromo-3-chloropyridine is employed as a reagent in the preparation of heterocycles and other organic compounds. Its unique structure and reactivity contribute to the synthesis of complex organic molecules for various applications.
Used in Research and Development:
Due to its potential as a versatile building block, 2-Bromo-3-chloropyridine is also used in research and development for exploring new chemical reactions and synthesizing novel compounds with potential applications in various industries.
Safety Precautions:
Given its irritant and toxic properties, 2-Bromo-3-chloropyridine must be handled and stored with proper precautions to minimize potential hazards. This includes using appropriate personal protective equipment and following safety guidelines to ensure the well-being of individuals working with 2-Bromo-3-chloropyridine.

InChI:InChI=1/C5H3BrClN/c6-5-4(7)2-1-3-8-5/h1-3H

Upstream product

• 626-60-8 3-Chloropyridine 
• 78948-09-1 acetyl hypofluorite 
• 73583-41-2 bromo-4 chloro-3 pyridine 
• 2402-77-9 2,3-dichloro-pyridine 
• 57266-69-0 3-chloropyridine-2-carboxylic acid 

Downstream Products

• 77332-89-9 2-iodo-3-pyridyl chloride 
• 186551-83-7 2-(4-bromophenoxy)-3-chloropyridine 
• 1355656-38-0 4-(5-chloro-6-cyclopropylpyridin-3-yloxy)-3-(2-methoxypyridin-3-yl)-N-(methylsulfonyl)benzamide 
• 1355657-13-4 3-bromo-4-(5-chloro-6-cyclopropylpyridin-3-yloxy)benzonitrile 
• 1355657-14-5 4-(5-chloro-6-cyclopropylpyridin-3-yloxy)-3-(2-methoxypyridin-3-yl)benzonitrile 
• 1355657-18-9 4-(5-chloro-6-cyclopropylpyridin-3-yloxy)-3-(2-methoxypyridin-3-yl)benzamide 
• 1386460-42-9 3-chloro-2-(2-fluoro-3-nitro-phenyl)-pyridine 
• 206357-78-0 tributyl-(3-chloro-2-pyridyl)stannane 

Relevant academic research and scientific papers

A PROCESS FOR THE PREPARATION OF SUBSTITUTED PYRIDINE COMPOUNDS AND INTERMEDIATES THEREOF

The present invention discloses a process for the preparation of substituted pyridine compounds of formula (I), comprises a step in which vinylogous nitriles of formula (II), are obtained from substituted α,β-unsaturated nitrile compounds of formula (III), and a further step of converting the vinylogous nitrile compounds of formula (II) into substituted pyridines of formula (I); wherein R1, R2, R3, R4 and LG are as defined in the description.

Transition-metal-free decarboxylative halogenation of 2-picolinic acids with dihalomethane under oxygen conditions

A convenient and efficient method for the synthesis of 2-halogen-substituted pyridines is described. The decarboxylative halogenation of 2-picolinic acids with dihalomethane proceeded smoothly via N-chlorocarbene intermediates to afford 2-halogen-substituted pyridines in satisfactory to excellent yields under transition-metal-free conditions. This new type of decarboxylative halogenation is operationally simple and exhibits high functional-group tolerance.

2-(PYRIDIN-2-YL)-PYRIMIDINES AND THEIR USE FOR CONTROLLING PATHOGENIC FUNGI

The invention relates to 2-(pyridin-2-yl)-pyrimidine compounds of general formula (I) and their use for controlling pathogenic fungi and as plant protection products that, as an active constituent, contain compounds of this type, whereby: k represents 0, 1, 2, 3; m represents 0, 1, 2, 3, 4 or 5; n represents 1, 2, 3, 4 or 5; R1, independent of one another, represents halogen, OH, CN, NO2, C1-C4 alkyl, C1-C4 alkyl halide, C1-C4 alkoxy, C1-C4 alkoxy halide, C2-C4 alkenyl, C2-C4 alkynyl, C3-C8 cycloalkyl, C1-C4 alkoxy-C1-C4 alkyl, amino, phenoxy, which is optionally substituted by halogen or C1-C4 alkyl, NHR, NR2, C(Ra)=N-ORb, S(=O)pA1 or C(=O)A2, or two radicals R1 bound to adjacent carbon atoms can, together, also represent a group -O-Alk-O-, wherein Alk represents a linear or branched C1-C4 alkylene, and 1, 2, 3 or 4 hydrogen atoms can also be replaced by halogen; R2 represents C1-C4 alkyl halide, C1-C4 alkoxy, C1-C4 alkoxy halide, hydroxy, halogen, CN or NO2; whereby R2 can also represent hydrogen or C1-C4 alkyl when at least one of the three following conditions is fulfilled: n represents 3, 4 or 5; k represents 1, 2 or 3; if m is not equal to 0, at least one of the radicals R1 represents a radical that differs from halogen, C1-C4 alkyl, C1-C4 alkoxy and C1-C4 alkyl halide, and; R3 represents C1-C4 alkyl.

Silyl-mediated halogen/halogen displacement in pyridines and other heterocycles

Heating with bromotrimethylsilane converts 2-chloropyridine into 2-bromopyridine and 2-chloro-6-methylpyridine into 2-bromo-6-methylpyridine. Both 2-chloropyridines and 2-bromopyridines give the corresponding iodo compound when treated with in situ generated iodotrimethylsilane. Although 3- and 4-chloropyridine are completely inert, 2,4-dichloropyridine undergoes the halogen/halogen exchange simultaneously at the 2- and 4-position. Halogen displacement takes place exclusively at the 2-position with 2,3-dichloropyridine and 2,5-dichloropyridine. In agreement with the intermediacy of N-trimethylsilylpyridinium salts as a prerequisite for the occurrence of halogen exchange, neither 2-fluoropyridine and 2-fluoro-6-methylpyridine nor any 2,6-dihalopyridine reacts. Finally, bromine/chlorine and iodine/chlorine substitution can also be accomplished with 2-or 4-chloroquinoline, 1-chloroisoquinoline, 2-chloropyrimidine, chloropyrazine and 2,3-dichloroquinoxaline as substrates. ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2002).

First regioselective c-2 lithiation of 3- and 4-chloropyridines

We have shown that the BuLi/LiDMAE reagent promotes the clean and regioselective C2 lithiation of 3- and 4-chloropyridines, while other reagents such as LDA or BuLi/TMEDA lead to classical ortho lithiation products or mixtures of regioisomers. The method was successfully applied to the preparation of various reactive 2,3- and 2,4-disubstituted pyridines.

Utilizing Acetyl Hypofluorite for Chlorination, Bromination, and Etherification of the Pyridine System

Acetyl hypofluorite, which is easily made from F2, possesses a strong electrophilic fluorine.This electrophile is able to attach itself to the nitrogen atom of pyridine and activate the ring toward nucleophilic attacks.The ultimate elimination of HF results in an overall easy nucleophilic displacement of the hydrogen of the important 2-position .The nucleophiles used: Clδ-, Brδ-, ROδ-, originate from solvents such as CH2Cl2, CH2Br2, and various primary alcohols.Thus, 2-halo- or 2-alkoxypyridines were formed.The reaction conditions (room temperature, very short reaction times, and good yields) transform the task of direct substitution of the pyridine ring from an extremely difficult to a very easy procedure.

Chlorination, Bromination, and Oxygenation of the Pyridine Ring Using AcOF Made from F2

Acetyl hypofluorite reacts with pyridines in halogenated solvents or alcohols to give the corresponding 2-halo- or 2-alkoxypyridines.

HOMOTRANSMETALLATION DES HALOGENO-3 PYRIDINES BROMEES EN -2 OU -4 PAR LE N-BUTYLLITHIUM. PROPOSITION D'UN NOUVEAU MECANISME DE TELESUBSTITUTION DU BROME.

These are new examples of the homotransmetallation reaction.Instead of the ordinary bromo-metal exchange it is possible to obtain selectively from the 2-bromo 3-fluoro or 2-bromo 3-chloro pyridines the 2-bromo 3-halogeno 4-lithio pyridines, which is very interesting for synthetic utility.From the 4-bromo 3-halogeno pyridines, we can see an isomerization with an halogen dance mechanism and we obtain the 5-bromo 3-halogeno 4-lithio pyridines.In the case of the 2-bromo 3-fluoro pyridine we explain a telesubstitution of bromine from 2 to 4 by a transitory homotransmetallation reaction during the Li-Br exchange.