108281-79-4

Basic information

• Product Name: 6-BROMO-1,2,4-TRIAZOLO[4,3-1]PYRIDINE
• Synonyms: 6-BROMO-TRIAZOLO[4,3-A]PYRIDINE;6-Bromo[1,2,4]triazolo[4,...;6-BROMO-1,2,4-TRIAZOLO[4,3-1]PYRIDINE;6-BROMO-[1,2,4]TRIAZOLO[4,3-A]PYRIDINE;6-Bromo-[1,2,4]triazolo[4,3-a]pyridine 98%
• CAS NO: 108281-79-4
• Molecular Formula: C₆H₄BrN₃
• Molecular Weight: 198.02006
• EINECS: 251-156-6
• Product Categories: blocks;Pyridines;Heterocycle-Pyridine series
• Mol File: 108281-79-4.mol
• Article Data: 6

Chemical Properties

• Melting Point: 151-153
• Appearance: /
• Density: 1.891 g/cm³
• Refractive Index: 1.751
• Storage Temp.: Keep Cold
• PKA: 2.38±0.50(Predicted)
• CAS DataBase Reference: 6-BROMO-1,2,4-TRIAZOLO[4,3-1]PYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-BROMO-1,2,4-TRIAZOLO[4,3-1]PYRIDINE(108281-79-4)
• EPA Substance Registry System: 6-BROMO-1,2,4-TRIAZOLO[4,3-1]PYRIDINE(108281-79-4)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 108281-79-4(Hazardous Substances Data)

Usage

Description

6-Bromo-1,2,4-triazolo[4,3-a]pyridine, commonly referred to as BTP, is a heterocyclic organic compound characterized by a molecular formula of C5H3BrN4. It features a pyridine ring fused to a triazole, which endows it with unique chemical and biological properties. BTP is recognized for its potential as a building block in the synthesis of pharmaceuticals and agrochemicals, making it a valuable component in the development of innovative drugs and crop protection products. Its versatility and biological activity have positioned BTP as a promising candidate for various applications across different fields, including medicine, agriculture, and materials science.

Uses

Used in Pharmaceutical Industry:
6-BROMO-1,2,4-TRIAZOLO[4,3-1]PYRIDINE is used as a building block for the synthesis of new drugs due to its unique chemical structure and biological activity. It contributes to the development of pharmaceuticals with potential applications in treating various diseases and conditions.
Used in Agrochemical Industry:
6-BROMO-1,2,4-TRIAZOLO[4,3-1]PYRIDINE is used as a key component in the formulation of agrochemicals, particularly in the development of crop protection products. Its incorporation into these products can enhance their effectiveness in protecting crops from pests and diseases, thereby improving agricultural productivity.
Used in Medicinal Chemistry Research:
6-BROMO-1,2,4-TRIAZOLO[4,3-1]PYRIDINE is used as a research compound for exploring its potential as an anti-inflammatory and anti-cancer agent. Its biological activity makes it a valuable tool for studying the mechanisms of these diseases and for identifying new therapeutic targets.
Used in Materials Science:
6-BROMO-1,2,4-TRIAZOLO[4,3-1]PYRIDINE is used in the development of novel materials with specific properties, such as high thermal stability, chemical resistance, or unique electronic characteristics. Its incorporation into these materials can lead to advancements in various industries, including electronics, aerospace, and automotive.

InChI:InChI=1/C6H4BrN3/c7-5-1-2-6-9-8-4-10(6)3-5/h1-4H

Upstream product

• 624-28-2 2,5-dibromopyridine 
• 77992-44-0 5-bromo-2-hydrazineylidene-1,2-dihydropyridine 
• 122-51-0 orthoformic acid triethyl ester 
• 77992-44-0 5-bromo-2-hydrazinylpyridine 
• 68-12-2 N,N-dimethyl-formamide 
• 50-00-0 formaldehyd 
• 14036-06-7 diethoxymethyl acetate 
• 53939-30-3 5-bromo-2-chloropyridine 

Downstream Products

• 1084810-52-5 8-([1,2,4]triazolo[4,3-a]pyridin-6-yl)-5-(3,5-difluorophenoxy)-2-methyl-2,3,4,5-tetrahydro-1H-benzo[c]azepine 
• 1609565-59-4 2,4-difluoro-N-(5-(3-(3-hydroxybut-1-yn-1-yl)-[1,2,4]-triazolo[4,3-a]pyridin-6-yl)-2-methoxypyridin-3-yl)benzenesulfonamide 
• 1609565-57-2 N-(5-([1,2,4]triazolo[4,3-a]pyridin-6-yl)-2-methoxypyridin-3-yl)-2,4-difluorobenzenesulfonamide 
• 1609565-56-1 2,4-difluoro-N-(5-(3-(3-hydroxyprop-1-yn-1-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-2-methoxypyridin-3-yl)benzenesulfonamide 
• 1609565-58-3 N-(5-(3-bromo-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-2-methoxypyridin-3-yl)-2,4-difluorobenzenesulfonamide 
• 1426845-31-9 2-(4-fluorophenyl)-5-(3-(4-fluorophenyl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide 
• 1426845-60-4 5-(3-bromo-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide 
• 1426845-59-1 5-([1,2,4]triazolo[4,3-a]pyridin-6-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide 
• 1313488-94-6 N-(5-([1,2,4]triazolo[4,3-a]pyridin-6-yl)-2-chloropyridin-3-yl)-4-fluorobenzenesulfonamide 
• 1262618-40-5 6-(4-(trifluoromethoxy)phenyl)-[1,2,4]triazolo[4,3-a]pyridine 

Relevant articles and documents

Discovery of Potent and Selective Non-Nucleotide Small Molecule Inhibitors of CD73

CD73 is an extracellular mediator of purinergic signaling. When upregulated in the tumor microenvironment, CD73 has been implicated in the inhibition of immune function through overproduction of adenosine. Traditional efforts to inhibit CD73 have involved antibody therapy or the development of small molecules, the most potent of which mimic the acidic and ionizable structure of the enzyme's natural substrate, adenosine 5′-monophosphate (AMP). Here, we report the systematic discovery of a novel class of non-nucleotide CD73 inhibitors that are more potent than all other nonphosphonate inhibitor classes reported to date. These efforts have culminated in the discovery of 4-({5-[4-fluoro-1-(2H-indazol-6-yl)-1H-1,2,3-benzotriazol-6-yl]-1H-pyrazol-1-yl}methyl)benzonitrile (73, IC50 = 12 nM) and 4-({5-[4-chloro-1-(2H-indazol-6-yl)-1H-1,2,3-benzotriazol-6-yl]-1H-pyrazol-1-yl}methyl)benzonitrile (74, IC50 = 19 nM). Cocrystallization of 74 with human CD73 demonstrates a competitive binding mode. These compounds show promise for the improvement of drug-like character via the attenuation of the acidity and low membrane permeability inherent to known nucleoside inhibitors of CD73.

Metal free [4+1] and [5+1] annulation reactions to prepare heterocycles using DMF and its derivatives as one-carbon source

1,2,4-Triazolo[3,4-a]pyridines and related heterocycles and substituted triazines were commonly discovered scaffolds in a variety of pharmaceutical and agrochemical agents. Herein, we report a highly efficient and practical method using DMF and its derivative for the [4+1] and [5+1] annulation reactions to prepare these heterocycles. This metal free reaction takes advantages of shelf stable DMF as solvent and carbon donor, imidazole chloride as a catalyst, the mild reaction condition tolerates a broad substrate range and substitutes. The prepared 3-unsubstituted 1,2,4-triazolo[3,4-a]pyridine and derivatives allow further introduction of a variety of functional group1 at 3-position.

HETEROAROMATIC COMPOUNDS AS PI3 KINASE MODULATORS AND METHODS OF USE

The present invention provides heteroaromatic derivatives and pharmaceutical acceptable salts and formulations thereof useful in modulating the protein kinase activity, especially phosphatidylinositol 3-kinases (PI3 kinases) and mTOR, and in modulating inter- and/or intra-cellular signaling activities such as proliferation, differentiation, apoptosis, migration and invasion. The invention also provides pharmaceutically acceptable compositions comprising such compounds and methods of using the compositions in the treatment of hyperproliferative disorders in mammals, especially humans.