835-71-2

Basic information

• Product Name: 2-(P-TOLYL)BENZOXAZOLE
• Synonyms: 2-(4-methylphenyl)-benzoxazol;2-(4-methylphenyl)benzoxazole;2-p-tolyl-benzoxazol;r619;2-(4-methylphenyl)-1,3-benzoxazole;4-(2-Benzoxazolyl)toluene;2-(4-Methylphenyl)-1,3-benzoxazole,2-p-tolylbenzo[d]oxazole;Benzoxazole, 2-(4-Methylphenyl)-Benzoxazole, 2-p-tolyl- (6CI,7CI,8CI)
• CAS NO: 835-71-2
• Molecular Formula: C₁₄H₁₁NO
• Molecular Weight: 209.24324
• EINECS: 212-643-6
• Mol File: 835-71-2.mol
• Article Data: 238

Chemical Properties

• Melting Point: 112-114℃
• Boiling Point: 309℃
• Flash Point: 125℃
• Appearance: /
• Density: 1.155
• Vapor Pressure: 0.00118mmHg at 25°C
• Refractive Index: 1.623
• PKA: 1.24±0.10(Predicted)
• CAS DataBase Reference: 2-(P-TOLYL)BENZOXAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(P-TOLYL)BENZOXAZOLE(835-71-2)
• EPA Substance Registry System: 2-(P-TOLYL)BENZOXAZOLE(835-71-2)

Safety Data

• Hazardous Substances Data: 835-71-2(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Synthetic Communications, 18, p. 1537, 1988 DOI: 10.1080/00397918808081311

InChI:InChI=1/C14H11NO/c1-10-6-8-11(9-7-10)14-15-12-4-2-3-5-13(12)16-14/h2-9H,1H3

Upstream product

• 57709-82-7 N-(2-hydroxy-phenyl)-4-methyl-benzamide 
• 117649-28-2 N-4-methylbenzylidene-2-hydroxyaniline 
• 624-31-7 4-tolyl iodide 
• 912350-80-2 2-{2-[N-(4-methoxybenzyl)acetamido]-2-phenylacetamido}phenyl 4-methylbenzoate 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 95-55-6 2-amino-phenol 
• 104-84-7 para-methylbenzylamine 
• 273-53-0 benzoxazole 
• 5720-05-8 4-methylphenylboronic acid 
• 36718-35-1 2-nitrophenyl 4-methylbenzoate 
• 98-59-9 p-toluenesulfonyl chloride 
• 583-55-1 1-Bromo-2-iodobenzene 
• 104-85-8 para-methylbenzonitrile 
• 459-44-9 4-methylbenzenediazonium tetrafluoroborate 

Downstream Products

• 16143-40-1 2-[4-(trans-2-thiophen-2-yl-vinyl)-phenyl]-benzooxazole 

Relevant articles and documents

DMF-Assisted Radical Cyclization of o-Isocyanodiaryl Ethers via 1,5-Aryl Migration: Construction of 2-Arylbenzoxazoles

A novel DMF-assisted radical cyclization of o-isocyanodiaryl ethers via 1,5-aryl migration has been developed for the synthesis of a series of 2-arylbenzoxazoles by the FeCl3/TBHP/Et3N catalytic system in DMF. However, N,N-dimethylbenzo[d]thiazole-2-carboxamide and N,N-dimethylbenzo[d]selenazole-2-carboxamide were obtained from the corresponding substrate 2-isocyanophenyl p-methoxyphenyl thioether and 2-isocyanodiphenyl selenoether under the same conditions. A possible mechanism may involve aryl 1,5-migration and DMF-assisted radical cyclization of o-isocyanodiaryl ethers.

Photocatalytic green synthesis of benzazoles from alcohol oxidation/toluene sp3C-H activation over metal-free BCN: effect of crystallinity and N-B pair exposure

Porous borocarbonitride (P-BCN), with the characteristics of enhanced crystallinity and improved N-B pair exposure, was prepared with a simple KCl-assisted molten salt strategy. Efficient heterogeneous photocatalytic tandem synthesis of benzazoles from alcohol oxidation/toluene sp3C-H activation was achieved firstly over the metal-free P-BCN using visible light and the green oxidant O2, with only water as a by-product. Variouso-thio/hydroxy/aminoanilines and alcohols or toluenes could be converted to the corresponding 2-substituted benzothiazoles, benzoxazoles and benzimidazoles with good to excellent photocatalytic performance. The improved photocatalytic performance in comparison to bulk BCN should be due to the crystallinity-enhancement-induced improvement in charge separation and transmission. The increased N-B pair exposure promoted superoxide radical generation due to the electron-enriched N atoms, as well as improved oxidation ability due to the valence band constructed by the B 2p orbital. This work presents a green and efficient synthetic strategy towards benzazoles and other fine chemicalsviametal-free heterogeneous photocatalysis.

TEMPO-mediated aerobic oxidative synthesis of 2-aryl benzoxazoles via ring-opening of benzoxazoles with benzylamines

A simple and efficient TEMPO-mediated system for aerobic oxidative synthesis of 2-aryl benzoxazoles from readily available benzoxazoles and primary benzylic and hetero benzylic amines is presented in one pot. The reaction proceeds through the ring-opening of benzoxazoles and is followed by oxidative condensation with benzylamines. These metal-free, straightforward reactions worked well with a wide range of substrates, yielding moderate to good yields under mild conditions using air as an external green oxidant.