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

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

Uses

Used in Pharmaceutical Industry:
5-Bromo-2-(piperidin-1-yl)pyridine is used as a key intermediate in the synthesis of various pharmaceutical products for its potential biological activity, contributing to drug discovery and development.
Used in Agrochemical Industry:
5-Bromo-2-(piperidin-1-yl)pyridine serves as a building block in the creation of agrochemicals, playing a crucial role in the development of new pesticides and other agricultural chemicals to improve crop protection and yield.
Used in Material Science:
5-Bromo-2-(piperidin-1-yl)pyridine is employed in the development of new materials, leveraging its chemical properties to enhance material performance in various applications.
Used in Chemical Process Development:
As a versatile compound in organic synthesis, 5-Bromo-2-(piperidin-1-yl)pyridine is utilized in the innovation and optimization of chemical processes, contributing to advancements in chemical production methods and techniques.

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 
• 201230-82-2 carbon monoxide 
• 475106-12-8 trifluoromethanesulfonic acid 5-bromo-pyridin-2-yl ester 
• 53939-30-3 5-bromo-2-chloropyridine 

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.

Inverting Conventional Chemoselectivity in Pd-Catalyzed Amine Arylations with Multiply Halogenated Pyridines

A new catalyst system capable of selective chloride functionalization in the Pd-catalyzed amination of 3,2- and 5,2- Br/Cl-pyridines is reported. A reaction optimization strategy employing ligand parametrization led to the identification of 1,1′-bis[bis(dimethylamino)phosphino]ferrocene "DMAPF", a readily available yet previously unutilized diphosphine, as a uniquely effective ligand for this transformation.

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.

Alkoxy- and amidocarbonylation of functionalised aryl and heteroaryl halides catalysed by a Bedford palladacycle and dppf: A comparison with the primary Pd(II) precursors (PhCN)2PdCl2 and Pd(OAc) 2

The versatility of a Bedford-type palladacycle 1, namely [{Pd(-Cl){κ2-P,C-P(OC6H2-2,4- tBu2)(OC6H3-2,4-tBu 2)2}}2], as a primary Pd source, in combination with the ligand bis-1,1′-(diphenylphosphino)ferrocene (dppf) has been established in carbonylation reactions of aryl and heteroaryl bromides with methanol, piperidine and related nucleophiles. Palladacycle 1 has been compared with other primary Pd sources, e.g. (PhCN)2PdCl2 and Pd(OAc)2. The efficacy of the carbonylation processes appear to be linked to the [Pd] concentration, substrate: catalyst ratio, CO pressure and reaction temperature. In amidocarbonylation, double carbonylation is observed for certain organohalides. In the case of 2,5-dibromopyridine, regioselective amination (Hartwig-Buchwald type) also occurs as a side-reaction. This journal is The Royal Society of Chemistry.

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.

INDOLES USEFUL IN THE TREATMENT OF INFLAMMATION

There is provided a compound of formula: (I), wherein X, R1, R2, R3, R4, R5 and R6 have meanings given in the description, and pharmaceutically-acceptable salts thereof, which compounds are useful in the treatment of diseases in which inhibition of the activity of microsomal prostaglandin E synthase-1 is desired and/or required, and particularly in the treatment of inflammation.

Methods for the synthesis of 5,6,7,8-tetrahydro-1,8-naphthyridine fragments for αvβ3 integrin antagonists

The preparation of 3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propan-1- amine 2a and 3-[(7R)-7-methyl-5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl]propan-1- amine 2b, key intermediates in the synthesis of αvβ 3 antagonists, is described. The syntheses rely on the efficient double Sonogashira reactions of 2,5-dibromopyridine 3 with acetylenic alcohols 4a/4b and protected propargylamines 10a-e followed by Chichibabin cyclizations of 3,3′-pyridine-2,5-diyldipropan-1-amines 9a/9b.

Selective Amination of Polyhalopyridines Catalyzed by a Palladium-Xantphos Complex

(Matrix presented) Amination of 5-bromo-2-chloropyridine (1a) catalyzed by a palladium-Xantphos complex predominately gives 5-amino-2-chloropyridine product 3a in 96% isolated yield and excellent chemoselectivity (3a/4a = 97:3). Amination of 2,5-dibromopyridine (11) under the same conditions exclusively affords 2-amino-5-bromopyridine 4a.