19520-27-5

Basic information

• Product Name: 5-bromo-2-(phenylthio)pyridine
• Synonyms: 5-bromo-2-(phenylthio)pyridine;5-Bromo-2-(phenylsulfanyl)pyridine
• CAS NO: 19520-27-5
• Molecular Formula: C₁₁H₈BrNS
• Molecular Weight: 266
• Mol File: 19520-27-5.mol

Chemical Properties

• Boiling Point: 367℃
• Flash Point: 176℃
• Appearance: /
• Density: 1.56
• CAS DataBase Reference: 5-bromo-2-(phenylthio)pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-bromo-2-(phenylthio)pyridine(19520-27-5)
• EPA Substance Registry System: 5-bromo-2-(phenylthio)pyridine(19520-27-5)

Safety Data

• Hazardous Substances Data: 19520-27-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
5-bromo-2-(phenylthio)pyridine is utilized as a versatile building block in organic synthesis for the creation of various pharmaceuticals and organic compounds. Its distinctive structure allows for multiple synthetic pathways, enhancing the diversity of molecules that can be synthesized.
Used in Pharmaceutical Research:
In pharmaceutical research, 5-bromo-2-(phenylthio)pyridine is employed as a key intermediate in the development of new drugs. Its reactivity and structural features make it a promising candidate for the synthesis of bioactive molecules with potential therapeutic applications.
Used as a Reagent in Chemical Reactions:
5-bromo-2-(phenylthio)pyridine also serves as a reagent in a variety of chemical reactions. Its participation in these reactions is crucial for the advancement of chemical processes and contributes to the broader understanding of organic chemistry mechanisms.
Overall, the applications of 5-bromo-2-(phenylthio)pyridine span across different sectors of the chemical industry, highlighting its significance in both research and practical applications.

Upstream product

• 223463-13-6 2-iodo-5-bromopyridine 
• 882-33-7 diphenyldisulfane 
• 56673-34-8 5-bromopyridine-2(1H)-thione 
• 98-80-6 phenylboronic acid 
• 872273-36-4 5-bromo-2-(2-(5-bromopyridin-2-yl)disulfanyl)pyridine 
• 624-28-2 2,5-dibromopyridine 
• 108-98-5 thiophenol 

Relevant articles and documents

Synthesis of 5-bromopyridyl-2-magnesium chloride and its application in the synthesis of functionalized pyridines

(Chemical Equation Presented) The 5-bromopyridyl-2-magnesium chloride (2), which was not accessible previously, was efficiently synthesized for the first time via an iodomagnesium exchange reaction with 5-bromo-2-iodopyridine (1). This reactive intermediate was allowed to react with a variety of electrophiles to afford a range of useful functionalized pyridine derivatives. Application of this methodology to 5-bromo-2-iodo-3-picoline provided a simple and economical synthesis of a key intermediate for the preparation of Lonafarnib, a potent anticancer agent.

Condensed compound and organic light emitting device comprising the same

Disclosed are a condensed cyclic compound represented by chemical formula 1 and having a novel structure, and an organic light emitting device containing the same. The organic light emitting device including the condensed cyclic compound may have a low driving voltage and a high efficiency.COPYRIGHT KIPO 2018

Pre-clinical characterization of aryloxypyridine amides as histamine H3 receptor antagonists: Identification of candidates for clinical development

The pre-clinical characterization of novel aryloxypyridine amides that are histamine H3 receptor antagonists is described. These compounds are high affinity histamine H3 ligands that penetrate the CNS and occupy the histamine H3 receptor in rat brain. Several compounds were extensively profiled pre-clinically leading to the identification of two compounds suitable for nomination as development candidates.

Desulfitative carbon-carbon cross-coupling of thioamide fragments with boronic acids

A novel and general carbon-carbon cross-coupling reaction between cyclic thioamides and boronic acids is described. The reaction is catalytic in palladium(O) and requires stoichiometric amounts of a copper(I) carboxylate as metal cofactor. The mode of cross-coupling in the reaction of cyclic thioamides with boronic acids is easily tunable between carbon-carbon and carbon-sulfur cross-coupling. While the catalytic palladium(O)/ copper(I) system provides carbon-carbon bond formation with extrusion of sulfur, stoichiometric quantities of copper(II) under air mediate carbon-sulfur bond formation.

Palladium(0)-catalyzed, copper(I)-mediated coupling of boronic acids with cyclic thioamides. Selective carbon-carbon bond formation for the functionalization of heterocycles

(Chemical Equation Presented) The palladium-catalyzed cross-coupling of cyclic thioamides with arylboronic acids in the presence of stoichiometric amounts of a copper(I) cofactor is described. The desulfitative carbon-carbon cross-coupling protocol is performed under neutral conditions and can be applied to a range of heterocyclic structures with embedded thioamide fragments. Successful carbon-carbon cross-coupling is independent of the ring size, aromaticity/nonaromaticity, the presence of additional heteroatoms, or other functional groups in the starting thioamide structure. Employing controlled microwave irradiation at 100°C, most cross-couplings can be completed within 2 h and proceed in high yields. An advantage of using thioamides as starting materials is die fact that the system can be tuned to an alternative carbon-sulfur cross-coupling pathway by changing to stoichiometric copper(II) under oxidative conditions. Both types of thioamide cross-couplings are orthogonal to the traditional base-catalyzed Suzuki-Miyaura cross-coupling of aryl halides with boronic acids.