1588769-34-9

Basic information

• Product Name: [1,2,4]Triazolo[1,5-A]Pyridine-6-Boronic Acid
• Synonyms: [1,2,4]Triazolo[1,5-A]Pyridine-6-Boronic Acid;[1,2,4]triazolo[1,5-a]pyridin-6-ylboronic acid;[1,2,4]Triazolo[1,5-A]Pyridine-6-Boronic Acid(WX654039)
• CAS NO: 1588769-34-9
• Molecular Formula: C₆H₆BN₃O₂
• Molecular Weight: 162.94174
• Mol File: 1588769-34-9.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• Density: 1.45±0.1 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 7.60±0.43(Predicted)
• CAS DataBase Reference: [1,2,4]Triazolo[1,5-A]Pyridine-6-Boronic Acid(CAS DataBase Reference)
• NIST Chemistry Reference: [1,2,4]Triazolo[1,5-A]Pyridine-6-Boronic Acid(1588769-34-9)
• EPA Substance Registry System: [1,2,4]Triazolo[1,5-A]Pyridine-6-Boronic Acid(1588769-34-9)

Safety Data

• Hazardous Substances Data: 1588769-34-9(Hazardous Substances Data)

Usage

General Description

[1,2,4]Triazolo[1,5-A]Pyridine-6-Boronic Acid is a chemical compound that belongs to the class of boronic acids. It is commonly used in organic synthesis and medicinal chemistry due to its ability to form stable complexes with diols and other nucleophiles. Boronic acids have been widely employed as building blocks for the preparation of various pharmaceuticals, agrochemicals, and materials. The [1,2,4]Triazolo[1,5-A]Pyridine-6-Boronic Acid is a versatile reagent that is useful for the functionalization of aromatic compounds and for the preparation of diverse heterocyclic structures. Overall, this chemical compound has important applications in the field of chemical research and drug development.

Upstream product

• 356560-80-0 6-bromo[1,2,4]triazolo[1,5-a]pyridine 
• 13675-18-8 tetrahydroxydiboron 
• 382592-25-8 N-(5-bromopyrid-2-yl)formamidoxime 
• 1072-97-5 5-bromo-2-pyridylamine 
• 150-46-9 triethyl borate 

Downstream Products

• 1236325-03-3 (S)-3-((S)-1-(4-([1,2,4]triazolo[1,5-a]pyridin-6-yl)phenyl)ethyl)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-one 

Relevant articles and documents

Pd- And Ni-Based Systems for the Catalytic Borylation of Aryl (Pseudo)halides with B2(OH)4

Despite recent advancements in metal-catalyzed borylations of aryl (pseudo)halides, there is a continuing need to develop robust methods to access both early-stage and late-stage organoboron intermediates amendable for further functionalization. In particular, the development of general catalytic systems that operate under mild reaction conditions across a broad range of electrophilic partners remains elusive. Herein, we report the development and application of three catalytic systems (two Pd-based and one Ni-based) for the direct borylation of aryl (pseudo)halides using tetrahydroxydiboron (B2(OH)4). For the Pd-based catalyst systems, we have identified general reaction conditions that allow for the sequestration of halide ions through simple precipitation that results in catalyst loadings as low as 0.01 mol % (100 ppm) and reaction temperatures as low as room temperature. We also describe a complementary Ni-based catalyst system that employs simple unligated Ni(II) salts as an inexpensive alternative to the Pd-based systems for the borylation of aryl (pseudo)halides. Extrapolation of all three systems to a one-pot tandem borylation/Suzuki-Miyaura cross-coupling is also demonstrated on advanced intermediates and drug substances.