132292-78-5

Basic information

• Product Name: 2-(4-fluorophenyl)-5-methyl-1,3-benzoxazole
• Synonyms: 2-(4-fluorophenyl)-5-methyl-1,3-benzoxazole
• CAS NO: 132292-78-5
• Molecular Formula: C₁₄H₁₀FNO
• Molecular Weight: 227.2337032
• Mol File: 132292-78-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(4-fluorophenyl)-5-methyl-1,3-benzoxazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-fluorophenyl)-5-methyl-1,3-benzoxazole(132292-78-5)
• EPA Substance Registry System: 2-(4-fluorophenyl)-5-methyl-1,3-benzoxazole(132292-78-5)

Safety Data

• Hazardous Substances Data: 132292-78-5(Hazardous Substances Data)

Upstream product

• 10531-78-9 5-methyl-1,3-benzoxazole 
• 462-06-6 fluorobenzene 
• 459-57-4 4-fluorobenzaldehyde 
• 95-84-1 3-amino-4-hydroxytoluene 
• 119-33-5 4-methyl-2-nitrophenol 
• 7292-73-1 (2RS)-N-(p-fluorophenyl)glycine 
• 352-33-0 1-Chloro-4-fluorobenzene 
• 766-98-3 1-ethynyl-4-fluorobenzene 
• 98-88-4 benzoyl chloride 
• 39833-45-9 3-(4-fluorophenyl)-1-phenylprop-2-yn-1-one 
• 183280-13-9 para-fluorophenyl pivalate 
• 6627-55-0 2-bromo-p-cresol 
• 456-14-4 4-fluorobenzamidine hydrochloride 
• 18441-43-5 5-methylbenzofuran 

Relevant articles and documents

Vibrational spectroscopic studies and ab initio calculations of 5-methyl-2-(p-fluorophenyl)benzoxazole

FT-Raman and FT-IR spectra of 5-methyl-2-(p-fluorophenyl)benzoxazole were recorded and analysed. The vibrational frequencies of the compound have been computed using the Hartree-Fock/6-31G* basis and compared with the experimental values.

Ni-Catalyzed C-H Arylation of Oxazoles and Benzoxazoles Using Pharmaceutically Relevant Aryl Chlorides and Bromides

This manuscript details the development of the nickel-catalyzed arylation of oxazoles and benzoxazoles with aryl halides. A series of aryl, heteroaryl, and druglike electrophiles relevant to pharmaceutical applications were surveyed. The desired arylated products were obtained in synthetically useful yields using electronically and structurally varied aryl halides. The use of microscale high-throughput experimentation was essential for both the rapid identification of optimal reaction parameters and the investigation of the aryl halide scope.

Synthesis of benzoxazoles via the copper-catalyzed hydroamination of alkynones with 2-aminophenols

We describe herein the synthetic method to benzoxazole derivatives via the copper-catalyzed hydroamination of alkynones with 2-aminophenols. The method produced a wide variety of functionalized benzoxazole derivatives in good yields. Preliminary mechanistic experiments revealed that the reaction would proceed through the copper-catalyzed hydroamination of alkynones and the sequential intramolecular cyclization of β-iminoketones/elimination of acetophenone promoted by the copper catalyst.

A benzoxazole for the arylation method (by machine translation)

The invention relates to a benzoxazole for the arylation method, comprises the following steps: under the protection of the inert gas, the benzoxazole, aryl/heteroaryl tosylates, catalyst nitrogen heterocyclic carbene - palladium complex, alkaline material, reaction solvent, in the 80 - 150 °C reaction 12 - 24 H of the reaction liquid obtained, then processing reaction liquid to obtain product, to obtain 2 - aryl benzoxazole. The invention discloses a benzoxazole for the arylation method development of novel catalytic system, catalyst stability, is easy to obtain, can make the stable, low price of the aryl/heteroaryl tosylates participate in the reaction, reaction operation is simple, low cost, product yield and purity and the like, has good value for research and industrial application produces the scenery. (by machine translation)

Unexpected Decarboxylation-Triggered o-Hydroxyl-Controlled Redox Condensation of Phenylglycines with 2-Nitrophenols in Aqueous Media

A decarboxylation-triggered and o-hydroxyl-controlled hydrogen-transfer strategy for the one-pot synthesis of benzoxazoles from readily available amino acids and 2-nitrophenols is reported. On the basis of this autoredox reaction, the C?N bond can be efficiently constructed to afford the desired products in moderate to good yields under transition-metal-free conditions in aqueous media. (Figure presented.).

Deep eutectic solvent-catalyzed arylation of benzoxazoles with aromatic aldehydes

A novel and efficient methodology for the arylation of benzoxazoles with aromatic aldehydes catalyzed by deep eutectic solvent has been developed. The reaction smoothly proceeded with a wide range of substrates to give the desired products in high yields within short reaction time. Deep eutectic solvents are easily recovered and reused without significant loss of catalytic activity.

Phosphonium acidic ionic liquid: An efficient and recyclable homogeneous catalyst for the synthesis of 2-Arylbenzoxazoles, 2-Arylbenzimidazoles, and 2-Arylbenzothiazoles

A highly efficient and green strategy for the synthesis of 2-Arylbenzoxazoles, 2-Arylbenzimidazoles, and 2-Arylbenzothiazoles catalyzed by phosphonium acidic ionic liquid has been developed via the condensation of o-Aminophenol, o-phenylenediamines, and o-Aminothiophenol, respectively, with aldehydes. The reaction has a good yield, the broad substrate scope, and mild condition. Triphenyl(butyl-3-sulphonyl)phosphonium toluenesulfonate catalyst was easily obtained from cheap and available starting materials through a one-pot synthesis. Its structure was identified by 1H NMR, 13C NMR, 31P NMR, and FT-IR techniques. Other properties including thermal stability and acidity were determined by TGA and Hammett acidity function method. Interestingly, the catalyst can maintain its constantly outstanding performance till the fourth recovery.

N-Heterocyclic Carbene (NHC)-Catalyzed One-Pot Aerobic Oxidative Synthesis of 2-Substituted Benzo[ d ]oxazoles, Benzo[ d ]thiazoles and 1,2-Disubstituted Benzo[ d ]imidazoles

N-Heterocyclic carbene (NHC), generated in situ from easily available N-heterocyclic imidazolium salt with air as terminal oxidant, has successfully been utilized as a cheap and efficient catalyst for one-pot aerobic oxidative synthesis of 2-arylbenzo[ d ]oxazoles, 2-substituted benzo[ d ]thiazoles, and 1,2-disubstituted benzo[ d ]imidazoles.

Nickel-catalyzed C?H arylation of benzoxazoles and oxazoles: Benchmarking the influence of electronic, steric and leaving group variations in phenolic electrophiles

Electronic, steric and leaving group effects for Ni-catalyzed direct arylations using C?O electrophiles were benchmarked. The scope of arylations with pivalates was general with respect to both the electronics on the electrophile and the azoles. Furthermore, the arylation of azoles with tosylates, mesylates and carbamates with varying electronics was explored, and showed electronic trends similar to those of the pivalate reactions. Finally, the relative rate of arylation of 5-methyl benzoxazole with two electronically-similar electrophiles bearing different leaving groups was established. The results from these studies implicate the following order of relative reactivity: mesylates>pivalates>carbamates.

Copper-catalyzed synthesis of benzoxazoles: Via tandem cyclization of 2-halophenols with amidines

This work reports a simple, efficient and alternative synthetic route for the preparation of benzoxazoles via tandem cyclization of 2-halophenols with amidines. The developed methodology is free from ligands and uses inexpensive and easily available CuCl as a catalyst. This protocol avoids the use of any oxidant or inorganic acids. Various benzoxazole derivatives were synthesized in good to excellent yields. To the best of our knowledge, this is the first time that the synthesis of benzoxazoles from 2-halophenols with both aromatic and aliphatic amidines is reported. Owing to the simplicity of this protocol, the preparation of benzoxazoles could be achieved at a gram scale level.