32959-62-9

Basic information

• Product Name: 2-(2-Pyridyl)benzoxazole
• Synonyms: 2-(2-Pyridyl)benzoxazole
• CAS NO: 32959-62-9
• Molecular Formula: C₁₂H₈N₂O
• Molecular Weight: 196.2
• Mol File: 32959-62-9.mol

Chemical Properties

• Melting Point: 101.0 to 105.0 °C
• Boiling Point: 150°C/0.4mmHg(lit.)
• Flash Point: 146.9°C
• Appearance: /
• Density: 1.241g/cm³
• Vapor Pressure: 0.000607mmHg at 25°C
• Refractive Index: 1.643
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: slightly sol. in Toluene
• PKA: 1.74±0.19(Predicted)
• CAS DataBase Reference: 2-(2-Pyridyl)benzoxazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-Pyridyl)benzoxazole(32959-62-9)
• EPA Substance Registry System: 2-(2-Pyridyl)benzoxazole(32959-62-9)

Safety Data

• Hazardous Substances Data: 32959-62-9(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 57, p. 2883, 1992 DOI: 10.1021/jo00036a025

InChI:InChI=1/C12H8N2O/c1-2-7-11-9(5-1)14-12(15-11)10-6-3-4-8-13-10/h1-8H

Upstream product

• 14178-31-5 (E)-2-pyridylphenyl ketoxime 
• 26825-30-9 (2-metoxy-phenyl)-pyridin-2-ylmethylene-amine 
• 13141-42-9 2-(2-phenylethynyl)pyridine 
• 95-55-6 2-amino-phenol 
• 110-86-1 pyridine 
• 273-53-0 benzoxazole 

Downstream Products

• 433713-00-9 [Re(OPPh₃)Cl₃(2-(2-pyridyl)benzoxazole))] 

Relevant articles and documents

Regiodivergent Cross-Dehydrogenative Coupling of Pyridines and Benzoxazoles: Discovery of Organic Halides as Regio-Switching Oxidants

Cross-dehydrogenative coupling (CDC) of two unfunctionalized heteroarenes has been recognized as an ideal transformation to synthesize privileged heterobiaryl scaffolds. However, regioselective activation and transformation of a specific set of two heterocyclic C-H bonds among other bonds have been extremely challenging. Thus, discovering a new controlling element to achieve regio-controlled and regio-divergent heterocyclic CDCs is considered crucial. In this Letter, the unprecedented use of organic halides as an oxidant to achieve the CDC reaction of pyridines and benzoxazoles with palladium catalyst is described. Moreover, the regioselectivity of the pyridine functionalization site can be controlled by the choice of organic halides.

Palladium-catalyzed synthesis of benzoxazoles by the cleavage reaction of carbon-carbon triple bonds with o-aminophenol

A novel and mild procedure for efficient synthesis of benzoxazoles by the cleavage reaction of carbon-carbon triple bonds with o-aminophenol in the presence of a catalytic amount of palladium chloride has been successfully developed, which provides rapid and efficient access to benzoxazoles. the Partner Organisations 2014.

Synthesis of 2-arylbenzoxazoles from flash vacuum pyrolysis of 2-methoxy-N-(arenylidene)anilines

Flash vacuum pyrolysis of 2-methoxy-N-(arenylidene)anilines 2a-g at 700 °C and 1 × 10-2 Torr gave the corresponding 2-arylbenzoxazoles 1a-g.

Flash Vacuum Pyrolysis of Aromatic Oximes

Flash vacuum pyrolisis (FVP) of benzaldoximes and aryl ketoximes afforded nitriles and additional aromatic compounds which were presumably generated from intermediary iminyl radicals.The FVP also gave benzoxazoles, which were presumably formed from iminoxyl radicals.Benzyl ketoximes afforded indoles together with fragmentation products of the iminyl radicals.Keyword---gas-phase pyrolysis; flash vacuum pyrolysis; FVP; flash thermolysis; oxime; iminyl radical; iminoxyl radical; substituted indole; benzoxazole; mass spectra