7420-86-2

Basic information

• Product Name: 5-methyl-2-phenylbenzoxazole
• Synonyms: 5-methyl-2-phenylbenzoxazole;witisol;2-PHENYL-5-METHYLBENZOXAZOLE;Einecs 231-040-9;5-methyl-2-phenylbenzo[d]oxazole;5-methyl-2-phenyl-1,3-benzoxazole
• CAS NO: 7420-86-2
• Molecular Formula: C₁₄H₁₁NO
• Molecular Weight: 209.24324
• EINECS: 231-040-9
• Mol File: 7420-86-2.mol
• Article Data: 102

Chemical Properties

• Melting Point: 108 °C
• Boiling Point: 314.7°C at 760 mmHg
• Flash Point: 128°C
• Appearance: /
• Density: 1.155g/cm³
• Vapor Pressure: 0.000847mmHg at 25°C
• Refractive Index: 1.623
• PKA: 2?+-.0.10(Predicted)
• CAS DataBase Reference: 5-methyl-2-phenylbenzoxazole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-methyl-2-phenylbenzoxazole(7420-86-2)
• EPA Substance Registry System: 5-methyl-2-phenylbenzoxazole(7420-86-2)

Safety Data

• Hazardous Substances Data: 7420-86-2(Hazardous Substances Data)

Usage

General Description

5-methyl-2-phenylbenzoxazole is a chemical compound with the molecular formula C15H13NO. It is a heterocyclic compound containing a benzoxazole ring with a phenyl and a methyl group attached to it. 5-methyl-2-phenylbenzoxazole is known for its fluorescent properties and is used as a fluorescence probe in various applications such as in the field of analytical chemistry, biochemistry, and materials science. It is also used in the synthesis of various organic compounds and pharmaceuticals due to its unique structural and chemical properties. Additionally, it has been studied for its potential biological activities and pharmacological effects. Overall, 5-methyl-2-phenylbenzoxazole is a versatile compound with diverse applications in various scientific and industrial fields.

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

Upstream product

• 110-86-1 pyridine 
• 64712-30-7 2-hydroxy-5-methylbenzophenone (E) oxime 
• 98-09-9 benzenesulfonyl chloride 
• 64-17-5 ethanol 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 854160-46-6 3-benzoylamino-4-benzoyloxy-toluene 
• 75-36-5 acetyl chloride 
• 93-63-0 2-benzoylamino-4-methyl-phenol 
• 19430-24-1 4-methyl-2-[(phenylmethylene)amino]phenol 
• 62103-87-1 6-methyl-3-phenyl-2H-benzo[b][1,4]oxazin-2-one 
• 591-50-4 iodobenzene 
• 201230-82-2 carbon monoxide 
• 452-84-6 3-amino-4-fluorotoluene 
• 878193-80-7 (E)-2-(benzylideneamino)-4-methylphenol 

Downstream Products

• 54785-43-2 5-bromomethyl-2-phenyl-benzooxazole 
• 95-84-1 3-amino-4-hydroxytoluene 
• 65-85-0 benzoic acid 
• 35875-76-4 5-methyl-2-(2-hydroxyphenyl)benzoxazole 

Relevant articles and documents

Cu-Catalyzed Synthesis of Benzoxazole with Phenol and Cyclic Oxime

A Cu-catalyzed straightforward synthesis of benzoxazoles from free phenols and cyclic oxime esters is reported. The mild reaction conditions tolerate various electron-withdrawing and electron-donating functional groups on both substrates, affording benzoxazoles in moderate to good yields. With this protocol, large-scale syntheses of Ezutromid and Flunoxaprofe in one or two steps are demonstrated. A catalytic mechanism, which includes Cu-catalyzed amination via inner-sphere electron transfer and consequent annulation, is proposed.

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.

One-Pot, Borax-mediated synthesis of structurally diverse N, S-heterocycles in water

Herein, a borax–mediated convenient and efficient strategy for the synthesis of prominent structurally diverse N, S-heterocycles such as quinazolin-4(3H)-one, benzothiadiazine 1,1-dioxide, benzothioazole, and benzoxazoles from readily available 2-aminobenzamide/2-aminobenzenesulfonamide/2-aminothiophenol/2-aminophenol with α,α,α-trihalotoluenes at 100 ℃ in water is elaborated. Upon using aldehydes instead of α,α,α-trihalotoluenes, the reactions proceed through domino fashion under the catalytic effect borax to yield 2,3-dihydroquinazolin-4(1H)-one, 3,4-dihydrothiadiazine 1,1-dioxide, and benzothiazoles in one-pot at 60 ℃. The advantages of this protocol are practical simplicity, large substrate scope, moderate to excellent yields, and the use of water as the solvent.