53573-22-1

Basic information

• Product Name: Isoxazole, 5-(4-bromophenyl)-3-phenyl-
• Synonyms: 5-(4-bromophenyl)-3-phenylisoxazole;3-Phenyl-5-(4-brom-phenyl)-isoxazol;5-(p-bromophenyl)-3-phenyl-2-isoxazole;Isoxazole,5-(4-bromophenyl)-3-phenyl;Phenyl-3p-bronphenyl-5-isoxazol (4c);HMS1674G08;5-(4-Brom-phenyl)-3-phenyl-isoxazol;3-phenyl-5-(p-bromophenyl)-isoxazole
• CAS NO: 53573-22-1
• Molecular Formula: C15H10BrNO
• Molecular Weight: 300.154
• Mol File: 53573-22-1.mol
• Article Data: 18

Chemical Properties

• CAS DataBase Reference: Isoxazole, 5-(4-bromophenyl)-3-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Isoxazole, 5-(4-bromophenyl)-3-phenyl-(53573-22-1)
• EPA Substance Registry System: Isoxazole, 5-(4-bromophenyl)-3-phenyl-(53573-22-1)

Safety Data

• Hazardous Substances Data: 53573-22-1(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 25856-01-3 1-(4-bromophenyl)-3-phenylpropane-1,3-dione 
• 7732-18-5 water 
• 623548-10-7 5-(4-bromophenyl)-4-iodo-3-phenylisoxazole 
• 100-42-5 styrene 
• 1122-91-4 4-bromo-benzaldehyde 
• 39833-48-2 3-(4-bromophenyl)-1-phenylprop-2-yn-1-one 
• 98-88-4 benzoyl chloride 
• 766-96-1 4-bromo-1-ethynylbenzene 
• 14525-88-3 1-(4-bromophenyl)-2-phenylcyclopropane 
• 586-75-4 4-chlorobenzoyl chloride 
• 532-27-4 1-chloroacetophenone 
• 22966-09-2 (2E)-3-(4-bromophenyl)-1-phenylprop-2-en-1-one 
• 698-16-8 benzohydroximoyl chloride 

Downstream Products

• 80223-14-9 5-(4-Bromo-phenyl)-2-methyl-3-phenyl-isoxazol-2-ium; iodide 
• 623548-10-7 5-(4-bromophenyl)-4-iodo-3-phenylisoxazole 

Relevant articles and documents

Method for synthesizing 3,5-disubstituted isoxazole compound based on three-component reaction

The invention provides a method for synthesizing a 3,5-disubstituted isoxazole compound based on three-component reaction, which comprises the following steps: mixing aldehyde, olefin and nitrite, and heating to react to generate the 3,5-disubstituted isoxazole compound. According to the scheme, the safety is greatly improved; the adopted raw materials can be commercially purchased and do not need to be prepared in advance, the reaction implementation is easier, and the reaction operation is simpler and more convenient; the application range of substrates is wider, and aliphatic hydrocarbon, aromatic hydrocarbon, condensed ring and other substrates can be suitable for the reaction system; the reaction can be carried out in both an acidic environment and an alkaline environment; the reaction can be carried out under an air condition without inert gas protection.

One-pot regioselective synthesis of substituted pyrazoles and isoxazoles in PEG-400/water medium by Cu-free nano-Pd catalyzed sequential acyl Sonogashira coupling-intramolecular cyclization

Catalyst efficacy of in situ generated Pd-nanoparticles (PdNPs) in the regioselective one-pot synthesis of 3,5-di & 3,4,5-trisubstituted pyrazoles and 3,5-disubstituted isoxazoles in environmentally benign PEG-400/H2O medium, which involves the sequential (i) Cu-free acyl-Sonogashira coupling (ASC) and (ii) intramolecular ynone-amine cyclization under PTC conditions was described. The results of controlled experiments support the operation of two sequential catalytic cycles (ASC/cyclization) and achievement of complementary/opposite regioselectivity via ynone-bound palladium in a one-pot approach. Moreover, the in situ PdNPs recovered after the first catalytic cycle of the one-pot reaction sequence have been reused again five times successively. Besides, prior to the above studies, the efficacy of some common Pd-N-heterocyclic carbene (Pd-NHC) complexes in catalyzing the same one-pot two-step reaction sequence (Cu-free ASC/cyclization) both in water and organic solvents was also optimized. In situ generation of PdNPs from above Pd-NHCs in water was also identified, but they are not reusable due to their large size distribution.

An Intramolecular Wittig Approach toward Heteroarenes: Synthesis of Pyrazoles, Isoxazoles, and Chromenone-oximes

α-Halohydrazones/ketoximes are transformed into trisubstituted pyrazoles/disubstituted isoxazoles by treatment with phosphine, acyl chloride, and a base. Mechanistic investigations revealed the in situ formation of azo/nitroso olefin intermediates which underwent a tandem phospha-Michael/N- or O-acylation/intramolecular Wittig reaction to afford the heteroarenes in moderate to good yields. Further, proper functionalization of α-haloketoximes and a change of conditions allowed the chemoselective synthesis of chromenone-oximes as well as rearranged isoxazoles, thereby realizing a diversity-oriented synthesis.