13466-43-8

Basic information

• Product Name: 3-Bromo-2-hydroxypyridine
• Synonyms: IFLAB-BB F1371-0174;3-BROMO-2-HYDROXYPYRIDINE;3-BROMO-2(1H)-PYRIDINONE;3-BROMO-2-PYRIDINOL;3-BROMO-2-PYRIDONE;3-BROMO-PYRIDIN-2-OL;2-HYDROXY-3-BROMOPYRIDINE;3-Bromo-2-Hydroxypyridine99%
• CAS NO: 13466-43-8
• Molecular Formula: C₅H₄BrNO
• Molecular Weight: 174
• EINECS: -0
• Product Categories: Pyridine;Pyridine Series;Bromopyridines;Halopyridines;Pyridines;Building Blocks;C5;C5 to C6;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks;alkyl bromide| alcohol
• Mol File: 13466-43-8.mol
• Article Data: 16

Chemical Properties

• Melting Point: 185-189°C
• Boiling Point: 336.6 °C at 760 mmHg
• Flash Point: 157.4 °C
• Appearance: White to off-white/Crystalline Powder
• Density: 1.776 g/cm³
• Vapor Pressure: 0.000111mmHg at 25°C
• Refractive Index: 1.6
• Storage Temp.: 2-8°C
• PKA: 10.53±0.10(Predicted)
• Water Solubility: Slightly soluble in water.
• BRN: 109846
• CAS DataBase Reference: 3-Bromo-2-hydroxypyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Bromo-2-hydroxypyridine(13466-43-8)
• EPA Substance Registry System: 3-Bromo-2-hydroxypyridine(13466-43-8)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36/37/38-41-37/38-22
• Safety Statements: 26-36-39
• WGK Germany: 3
• Hazardous Substances Data: 13466-43-8(Hazardous Substances Data)

Usage

Description

3-Bromo-2-hydroxypyridine is an organic compound characterized by its light yellow powder form. It is a derivative of pyridine, a basic nitrogen-containing structure, with a bromine atom at the 3rd position and a hydroxyl group at the 2nd position. 3-Bromo-2-hydroxypyridine is known for its potential applications in various fields due to its unique chemical properties.

Uses

Used in Pharmaceutical Industry:
3-Bromo-2-hydroxypyridine is used as an active ingredient in the development of pharmaceuticals for medicine. Its specific structural features make it a valuable component in the synthesis of various drug candidates, contributing to the treatment of different health conditions.
Used in Chemical Synthesis:
3-Bromo-2-hydroxypyridine is used as a key intermediate in the synthesis of pyrazolopyridines, which are known as γ-secretase modulators. These modulators play a significant role in the regulation of cellular processes and have potential therapeutic applications in the treatment of neurodegenerative diseases such as Alzheimer's.

InChI:InChI=1/C5H4BrNO/c6-4-2-1-3-7-5(4)8/h1-3H,(H,7,8)

Upstream product

• 98273-62-2 acetic acid-(3-bromo-[2]pyridyl ester) 
• 142-08-5 2-hydroxypyridin 
• 13472-81-6 3,5-dibromo-2-hydroxypyridine 
• 13534-99-1 2-Amino-3-bromopyridine 
• 142-08-5 2-Pyridone 
• 98976-74-0 Diethyl-carbamic acid 3-bromo-pyridin-2-yl ester 
• 98976-68-2 2-pyridyl N,N-diethylcarbamate 
• 52200-48-3 3-bromo-2-chloropyridine 

Downstream Products

• 13472-81-6 3,5-dibromo-2-hydroxypyridine 
• 52200-49-4 3-bromo-2-(phenylmethoxy)pyridine 
• 81971-38-2 3-bromo-1-methyl-1H-pyridin-2-one 
• 13472-59-8 3-Bromo-2-methoxypyridine 
• 13466-35-8 3-chloro-2-hydroxypyridine 
• 330943-61-8 tert-butyl-phenyl-phosphinothioic acid O-(3-bromo-pyridin-2-yl) ester 
• 426823-57-6 3-bromo-1-(1-phenyl-2-pyrrolidin-1-yl-ethyl)-1H-pyridin-2-one 
• 637348-81-3 3-bromo-5-iodopyridin-2-ol 

Relevant articles and documents

HETEROCYCLIC COMPOUNDS AS ADENOSINE ANTAGONISTS

Aminopyrazine compounds as modulators of an adenosine receptor are provided. The compounds may find use as therapeutic agents for the treatment of diseases mediated through a G-protein-coupled receptor signaling pathway and may find particular use in oncology.

Macrocyclic Modulators of the Ghrelin Receptor

The present invention provides novel conformationally-defined macrocyclic compounds that have been demonstrated to be selective modulators of the ghrelin receptor (growth hormone secretagogue receptor, GHS-R1a and subtypes, isoforms and variants thereof). Methods of synthesizing the novel compounds are also described herein. These compounds are useful as agonists of the ghrelin receptor and as medicaments for treatment and prevention of a range of medical conditions including, but not limited to, metabolic and/or endocrine disorders, gastrointestinal disorders, cardiovascular disorders, obesity and obesity-associated disorders, central nervous system disorders, genetic disorders, hyperproliferative disorders and inflammatory disorders.

Antimalarial Inhibitors Targeting Serine Hydroxymethyltransferase (SHMT) with in Vivo Efficacy and Analysis of their Binding Mode Based on X-ray Cocrystal Structures

Target-based approaches toward new antimalarial treatments are highly valuable to prevent resistance development. We report several series of pyrazolopyran-based inhibitors targeting the enzyme serine hydroxymethyltransferase (SHMT), designed to improve microsomal metabolic stability and to identify suitable candidates for in vivo efficacy evaluation. The best ligands inhibited Plasmodium falciparum (Pf) and Arabidopsis thaliana (At) SHMT in target assays and PfNF54 strains in cell-based assays with values in the low nanomolar range (3.2-55 nM). A set of carboxylate derivatives demonstrated markedly improved in vitro metabolic stability (t1/2 > 2 h). A selected ligand showed significant in vivo efficacy with 73% of parasitemia reduction in a mouse model. Five new cocrystal structures with PvSHMT were solved at 2.3-2.6 ? resolution, revealing a unique water-mediated interaction with Tyr63 at the end of the para-Aminobenzoate channel. They also displayed the high degree of conformational flexibility of the Cys364-loop lining this channel.