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

• 20389-05-3 2-p-tolyl-Cinchoninic acid 
• 51-19-4 2-aminophenol hydrochloride 
• 104-85-8 para-methylbenzonitrile 
• 95-55-6 2-amino-phenol 
• 104-87-0 4-methyl-benzaldehyde 
• 88-75-5 2-hydroxynitrobenzene 
• 99-94-5 p-Toluic acid 
• 57774-66-0 N-(Ethoxycarbonyl)-4-methylbenzenethiocarboxamide 
• 67213-27-8 p-methylselenobenzamide 
• 57709-82-7 N-(2-hydroxy-phenyl)-4-methyl-benzamide 
• 117649-28-2 N-4-methylbenzylidene-2-hydroxyaniline 
• 93099-43-5 2-nitrophenyl 4-methylbenzylether 
• 19865-55-5 N-(4-methylbenzylidene)aniline oxide 
• 589-18-4 4-Methylbenzyl alcohol 

Downstream Products

• 16143-40-1 2-[4-(trans-2-thiophen-2-yl-vinyl)-phenyl]-benzooxazole 
• 64893-57-8 2-{4-[4-(3-phenyl-[1,2,4]oxadiazol-5-yl)-trans-styryl]-phenyl}-benzooxazole 
• 64893-36-3 2-{4-[4-(5-phenyl-[1,2,4]oxadiazol-3-yl)-trans-styryl]-phenyl}-benzooxazole 
• 72093-68-6 2-(4-{4-[5-(4-chloro-phenyl)-[1,2,4]oxadiazol-3-yl]-trans-styryl}-phenyl)-benzooxazole 
• 64893-30-7 2-(4-{4-[3-(4-methoxy-phenyl)-[1,2,4]oxadiazol-5-yl]-trans-styryl}-phenyl)-benzooxazole 
• 64893-37-4 2-(4-{4-[5-(4-methoxy-phenyl)-[1,2,4]oxadiazol-3-yl]-trans-styryl}-phenyl)-benzooxazole 
• 53348-69-9 2-{4-[trans-2-(2-phenyl-benzofuran-6-yl)-vinyl]-phenyl}-benzooxazole 
• 16143-15-0 2-[4-(trans-2-biphenyl-4-yl-vinyl)-phenyl]-benzooxazole 
• 1552-56-3 (E)-2-(stilben-4-yl)-1,3-benzoxazole 
• 35379-61-4 2-[4-(4-benzooxazol-2-yl-trans-styryl)-phenyl]-7-phenyl-2,7-dihydro-benzo[1,2-d;3,4-d']bis[1,2,3]triazole 
• 53348-63-3 2-[4-(4-trans-styryl-trans-styryl)-phenyl]-benzooxazole 
• 16143-07-0 (E)-2-(4-chlorostilben-4'-yl)-1,3-benzoxazole 
• 59136-21-9 2-{4-[2-(5-methyl-2-phenyl-2H-[1,2,3]triazol-4-yl)-vinyl]-phenyl}-benzooxazole 
• 61519-73-1 2-(4-{2-[2-(4-chloro-phenyl)-2H-[1,2,3]triazol-4-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.

Nickel catalyzed sustainable synthesis of benzazoles and purines: Via acceptorless dehydrogenative coupling and borrowing hydrogen approach

Herein we report nickel-catalyzed sustainable synthesis of a few chosen five-membered fused nitrogen heterocycles such as benzimidazole, purine, benzothiazole, and benzoxazole via acceptorless dehydrogenative functionalization of alcohols. Using a bench stable, easy to prepare, and inexpensive Ni(ii)-catalyst, [Ni(MeTAA)] (1a), featuring a tetraaza macrocyclic ligand (tetramethyltetraaza[14]annulene (MeTAA)), a wide variety of polysubstituted benzimidazole, purine, benzothiazole, and benzoxazole derivatives were prepared via dehydrogenative coupling of alcohols with 1,2-diaminobenzene, 4,5-diaminopyrimidine, 2-aminothiphenol, and 2-aminophenol, respectively. A wide array of benzimidazoles were also prepared via a borrowing hydrogen approach involving alcohols as hydrogen donors and 2-nitroanilines as hydrogen acceptors. A few control experiments were performed to understand the reaction mechanism.

Stable Pd(0) Complexes with Ferrocene Bisphosphanes Bearing Phosphatrioxaadamantyl Substituents Efficiently Catalyze Selective C-H Arylation of Benzoxazoles by Aryl Chlorides

Versatile applications and unique performance of 1,1’-bis(diphenylphosphanyl)ferrocene (dppf) in coordination chemistry and catalysis prompted the search for its analogs. This contribution describes the synthesis of the first donor-unsymmetric dppf congeners bearing bulky and rigid 1,3,5,7-tetramethyl-2,4,6-trioxa-8-phosphaadamantyl (CgP) donor groups, viz. Ph2PfcPCg (1) and Ph2PfcCH2PCg (2; fc=ferrocene-1,1’-diyl). Bis-phosphanes 1 and 2 were converted into air-stable Pd(0) complexes, [Pd(ma)(L^L)] (L^L=1 and 2; ma=maleic anhydride). Together with [Pd(ma)(dppf)], these complexes were applied as catalysts in Pd-catalyzed C?H arylation of benzoxazoles with aryl chlorides in n-butanol as an environmentally benign solvent. Among all catalysts tested in this study, complex [Pd(ma)(2)] performed the best, providing a high-yield and selective synthesis of 2-arylbenzoxazoles from a range of the generally less reactive chloroarenes at low catalyst loading (typically 1 mol.%). Under similar conditions, the structurally related heterocycles (e. g., 1-methylbenzimidazole and benzothiazole) did not react.