24255-95-6

Basic information

• Product Name: 5-Bromo-2-(piperidin-1-yl)pyridine
• Synonyms: 5'-bromo-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl;1-(5-Bromopyridin-2-yl)piperidine
• CAS NO: 24255-95-6
• Molecular Formula: C₁₀H₁₃BrN₂
• Molecular Weight: 241.14
• Product Categories: pharmacetical;Pyridine;Amino;Organohalides
• Mol File: 24255-95-6.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 333.852 °C at 760 mmHg
• Flash Point: 155.708 °C
• Appearance: /
• Density: 1.409 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.579
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 5-Bromo-2-(piperidin-1-yl)pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Bromo-2-(piperidin-1-yl)pyridine(24255-95-6)
• EPA Substance Registry System: 5-Bromo-2-(piperidin-1-yl)pyridine(24255-95-6)

Safety Data

• Hazard Codes: Xi,Xn
• Hazardous Substances Data: 24255-95-6(Hazardous Substances Data)

Usage

General Description

5-Bromo-2-(piperidin-1-yl)pyridine is a chemical compound with the molecular formula C11H14BrN2. It is a pyridine derivative containing a bromine atom and a piperidine group. 5-Bromo-2-(piperidin-1-yl)pyridine is commonly used as a building block in the synthesis of various pharmaceutical and agrochemical products, as well as in the development of new materials and chemical processes. It has demonstrated potential biological activity in research studies, making it a valuable tool for drug discovery and development. Additionally, 5-Bromo-2-(piperidin-1-yl)pyridine is known for its versatility in organic synthesis, making it a valuable and widely utilized compound in the field of chemistry.

InChI:InChI=1/C10H13BrN2/c11-9-4-5-10(12-8-9)13-6-2-1-3-7-13/h4-5,8H,1-3,6-7H2

Upstream product

• 110-89-4 piperidine 
• 624-28-2 2,5-dibromopyridine 
• 53939-30-3 5-bromo-2-chloropyridine 
• 201230-82-2 carbon monoxide 
• 475106-12-8 trifluoromethanesulfonic acid 5-bromo-pyridin-2-yl ester 

Downstream Products

• 501378-38-7 6-(piperidin-1-yl)nicotinonitrile 

Relevant articles and documents

Ni-Catalyzed Reductive Cyanation of Aryl Halides and Phenol Derivatives via Transnitrilation

Herein, we report a Ni-catalyzed reductive coupling for the synthesis of benzonitriles from aryl (pseudo)halides and an electrophilic cyanating reagent, 2-methyl-2-phenyl malononitrile (MPMN). MPMN is a bench-stable, carbon-bound electrophilic CN reagent that does not release cyanide under the reaction conditions. A variety of medicinally relevant benzonitriles can be made in good yields. Addition of NaBr to the reaction mixture allows for the use of more challenging aryl electrophiles such as aryl chlorides, tosylates, and triflates. Mechanistic investigations suggest that NaBr plays a role in facilitating oxidative addition with these substrates.

Role of copper in catalyzing aryl and heteroaryl-nitrogen (or -oxygen) bond formation under ligand-free and solvent-free conditions

Formation of aryl- or heteroaryl-nitrogen (or -oxygen) bonds under ligand and solvent-free conditions are highly selective to the presence of copper. While bromoarenes undergo C-N (or -O) coupling in stoichiometric presence of copper, heteroaryl bromides require only catalytic amounts of copper(I) salts depending on the position of bromo substituents. Such selectivity coupled with ligand and solvent-free protocols appear promising from the viewpoint of ecology and economy and are more attractive as compared to the existing protocols.

4-Amino-5-aryl-6-arylethynylpyrimidines: Structure-activity relationships of non-nucleoside adenosine kinase inhibitors

A series of non-nucleoside adenosine kinase (AK) inhibitors is reported. These inhibitors originated from the modification of 5-(3-bromophenyl)-7-(6-morpholin-4-ylpyridin-3-yl)pyrido[2,3-d]pyrimidin-4-ylamine (ABT-702). The identification of a linker that would approximate the spatial arrangement found between the pyrimidine ring and the aryl group at C(7) in ABT-702 was a key element in this modification. A search of potential linkers led to the discovery of an acetylene moiety as a suitable scaffold. It was hypothesized that the aryl acetylenes, ABT-702, and adenosine bound to the active site of AK (closed form) in a similar manner with respect to the orientation of the heterocyclic base. Although potent acetylene analogs were discovered based on this assumption, an X-ray crystal structure of 5-(4-dimethylaminophenyl)-6-(6-morpholin-4-ylpyridin-3-ylethynyl)pyrimidin-4-ylamine (16a) revealed a binding orientation contrary to adenosine. In addition, this compound bound tightly to a unique open conformation of AK. The structure-activity relationships and unique ligand orientation and protein conformation are discussed.