26163-07-5

Usage

Uses

Used in Organic Synthesis:
5-Bromo-2-(dimethylamino)pyridine is used as a reagent for the formation of C-N and C-O bonds in organic synthesis. Its presence facilitates the creation of new chemical entities, contributing to the development of novel compounds with potential applications in various fields.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 5-Bromo-2-(dimethylamino)pyridine is utilized for the synthesis of various drugs. Its unique structure allows for the development of new therapeutic agents with improved efficacy and selectivity, addressing unmet medical needs.
Used in Agrochemical Production:
5-Bromo-2-(dimethylamino)pyridine is employed as a building block in the production of agrochemicals. Its incorporation into these compounds can enhance their effectiveness in protecting crops from pests and diseases, thereby increasing agricultural productivity.
Used in Dye Manufacturing:
In the dye industry, 5-Bromo-2-(dimethylamino)pyridine is used as a key component in the synthesis of various dyes. Its presence in these dyes can improve their colorfastness, brightness, and stability, making them suitable for a wide range of applications, including textiles, plastics, and printing inks.
Overall, 5-Bromo-2-(dimethylamino)pyridine is a versatile chemical compound with a broad spectrum of applications across different industries, including organic synthesis, pharmaceuticals, agrochemicals, and dyes. Its unique structure and properties make it an essential reagent and building block in the development of innovative products and solutions.

InChI:InChI=1/C7H9BrN2/c1-10(2)7-4-3-6(8)5-9-7/h3-5H,1-2H3

Upstream product

• 77-78-1 dimethyl sulfate 
• 5683-33-0 2-(Dimethylamino)pyridine 
• 37026-85-0 tri-n-butylammonium bromide 
• 624-28-2 2,5-dibromopyridine 
• 68-12-2 N,N-dimethyl-formamide 
• 766-11-0 5-bromo-2-fluoropyridine 
• 475106-12-8 trifluoromethanesulfonic acid 5-bromo-pyridin-2-yl ester 
• 1072-97-5 5-bromo-2-pyridylamine 
• 506-59-2 N,N-dimethylammonium chloride 
• 124-40-3 dimethyl amine 
• 74-88-4 methyl iodide 
• 50-00-0 formaldehyd 
• 7664-93-9 sulfuric acid 
• 3618-79-9 2-(dimethylamino)pyridine 1-oxide 

Downstream Products

• 579525-46-5 6-(dimethylamino)pyridin-3-ylboronic acid 
• 149805-92-5 6-(dimethylamino)nicotine-3-carboxaldehyde 
• 1242333-49-8 tert-butyl N-[6-(dimethylamino)-3-pyridyl]carbamate 
• 5683-33-0 2-(Dimethylamino)pyridine 
• 154924-17-1 N'-(5-cyanopyridin-2-yl)-N,N-dimethylformamidine 
• 1426259-44-0 N,N-dimethyl-5-(4-{2-[(6-methylpyridin-2-yl)amino]-1,3-thiazol-4-yl}phenyl)pyridin-2-amine 
• 1228652-40-1 4-(6-dimethylamino-pyridin-3-yl)-4-hydroxy-cyclohexanone 
• 1083329-54-7 5-N-benzylamino-2-N,N-dimethylaminopyridine 
• 4928-43-2 N₂,N₂-dimethylpyridine-2,5-diamine 

Relevant academic research and scientific papers

Discovery of Pyrazolopyridones as a Novel Class of Gyrase B Inhibitors Using Structure Guided Design

The ATPase subunit of DNA gyrase B is an attractive antibacterial target due to high conservation across bacteria and the essential role it plays in DNA replication. A novel class of pyrazolopyridone inhibitors was discovered by optimizing a fragment screening hit scaffold using structure guided design. These inhibitors show potent Gram-positive antibacterial activity and low resistance incidence against clinically important pathogens.

Photoassisted Charge Transfer Between DMF and Substrate: Facile and Selective N,N-Dimethylamination of Fluoroarenes

A reversible Van der Waals complex formation between the electron-deficient fluorinated aromatic ring and N,N-dimethylformamide (DMF) molecules followed by light irradiation resulted in charge transfer (CT) process. The complex was stabilized by ammonium formate and further decomposed to form the C?N bond. Control experiments revealed that the simultaneous SNAr pathway also contributes to product formation. This methodology is mild, metal-free, and effective for the amination of a variety of substrates. The reproducibility of this methodology was also verified on gram-scale reactions. The CT states were supported by control UV/Vis spectroscopy and computational studies.

Directing Group Enables Electrochemical Selectively Meta-Bromination of Pyridines under Mild Conditions

Without the use of catalysts and oxidants, a facile and sustainable electrochemical bromination protocol was developed. By introducing the directing groups, the regioselectivity of pyridine derivatives could be controlled at themeta-position utilizing the inexpensive and safe bromine salts at room temperature. A variety of brominated pyridine derivatives were obtained in 28-95% yields, and the reaction could be readily performed at a gram scale. By combining the installation and removing the directing group, the concept ofmeta-bromination of pyridines could be verified.

Aryl-Diadamantyl Phosphine Ligands in Palladium-Catalyzed Cross-Coupling Reactions: Synthesis, Structural Analysis, and Application

Synthesis, temperature-dependent NMR structure investigation and utilization of a new, stable and easily accessible aryl-diadamantylphosphine ligand family is reported. The bulky and electron-rich phosphorus center of the ligand enhances the catalytic activity of palladium in cross-coupling reactions of sterically demanding ortho-substituted aryl halides. In our study, we demonstrated the synthetic applicability of the new phosphine ligands in Buchwald-Hartwig and tosyl hydrazone coupling reactions.

A Novel One-Pot Synthesis of N,N-Dimethylaminopyridines by Diazotization of Aminopyridines in Dimethylformamide in the Presence of Trifluoromethanesulfonic Acid

Abstract: Diazotization of aminopyridines in the presence of trifluoromethanesulfonic acid gives the corresponding pyridinyl trifluoromethanesulfonates instead of expected diazonium salts. Pyridinyl trifluoromethanesulfonates can be converted to N,N-dimethylaminopyridines on heating in dimethylformamide via replacement of the trifluoromethanesulfonyloxy group. The reaction is accelerated under microwave irradiation. A novel one-pot procedure has been proposed for the synthesis of 2- and 4-(dimethylamino)pyridines from commercially available aminopyridines. The procedure provides high yields of the target products, and it can be regarded as an alternative to the known methods of synthesis of N,N-dimethylpyridin-4-amine (DMAP) widely used as base catalyst in organic synthesis.

Iron-catalyzed protodehalogenation of alkyl and aryl halides using hydrosilanes

A simple and efficient iron-catalyzed protodehalogenation of alkyl and aryl halides using phenylhydrosilane is disclosed. The reaction utilizes FeCl3 without the requirement of ligands. Unactivated alkyl and aryl halides were successfully reduced in good yields; sterically hindered tertiary halides were also reduced including the less reactive chlorides. The scalability of this methodology was demonstrated by a gram-scale synthesis with a catalyst loading as low as 0.5 mol%. Notably, disproportionation of phenylsilane leads to diphenylsilane that further reduces the halides. Preliminary mechanistic studies revealed a non-radical pathway and the source of hydrogen is PhSiH3via deuterium labeling studies. Our methodology represents simplicity and provides a good alternative to typical tin, aluminum and boron hydride reagents.

DUAL ATM AND DNA-PK INHIBITORS FOR USE IN ANTI-TUMOR THERAPY

Provided herein are compounds of the Formula (I), (II), and (III), as well as pharmaceutically acceptable salts thereof, wherein the substituents are those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment of oncologic diseases.

Environmentally benign indole-catalyzed position-selective halogenation of thioarenes and other aromatics

Halogenated aromatic compounds are the cores of many pharmaceutical, agricultural and chemical products but they are commonly prepared using electrophilic halogenation reactions in non-green chlorinated solvents under harsh conditions. A separate problem happens in the aromatic halogenation of thioarenes because they readily undergo oxidative side-reactions. Herein we report an environmentally benign electrophilic bromination of aromatics using an indole-catalytic protocol, which is suitable for a wide range of substrates including thioarenes.

Novel green and practical synthesis method of N,N-dimethyl pyridine compound

The invention relates to a novel green and practical synthesis method of a N,N-dimethyl pyridine compound. The reaction method is characterized in that common inorganic alkaline and water are respectively used as an accelerant and a reaction solvent; under the mild condition and in air, 2-halogenated pyridine derivatives and N,N-dimethylformamide compounds can be smoothly promoted to selectively perform dehalogenation amination reaction to generate corresponding N,N-dimethyl pyridine derivatives. The direct amination reaction of cheap and easy-to-obtain inorganic alkaline promoted 2-halogenated pyridine compounds and N,N-disubstituted methylformamide compounds is innovatively realized for the first time; the limitation that a metallic catalyst needs to be used by a traditional method is overcome; a bran-new strategy is provided for laboratory preparation and industrial production of the N,N-dimethyl pyridine compound.

SUBSTITUTED BENZAZINONES AS ANTIBACTERIAL COMPOUNDS

The present invention relates to LpxC antibacterial compounds of Formula (1A), corresponding pharmaceutically acceptable salts thereof, corresponding pharmaceutical compositions:, compound preparation, treatment methods and uses for bacterial infections, especially those caused by gram-negative bacteria.