96908-21-3

Basic information

• Product Name: Oxazole, 5-(4-bromophenyl)-2-phenyl-
• CAS NO: 96908-21-3
• Molecular Formula: C15H10BrNO
• Molecular Weight: 300.154
• Mol File: 96908-21-3.mol
• Article Data: 17

Chemical Properties

• CAS DataBase Reference: Oxazole, 5-(4-bromophenyl)-2-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Oxazole, 5-(4-bromophenyl)-2-phenyl-(96908-21-3)
• EPA Substance Registry System: Oxazole, 5-(4-bromophenyl)-2-phenyl-(96908-21-3)

Safety Data

• Hazardous Substances Data: 96908-21-3(Hazardous Substances Data)

Upstream product

• 98-88-4 benzoyl chloride 
• 72571-06-3 5-(4-bromophenyl)oxazole 
• 591-50-4 iodobenzene 
• 2039-82-9 1-bromo-4-ethenyl-benzene 
• 100-46-9 benzylamine 
• 99-73-0 para-bromophenacyl bromide 
• 3185-50-0 N-(4-bromophenethyl)benzamide 
• 2403-27-2 1-(4-bromophenyl)-3-phenyl-2-propen-1-one 
• 766-96-1 4-bromo-1-ethynylbenzene 
• 61650-22-4 N-(pivaloyloxy)benzamide 
• 582-61-6 benzoyl azide 
• 126443-12-7 4'-bromo-4-methoxy-trans-chalcone 
• 72997-91-2 4-(4-bromo-phenyl)-(trans-3-phenyl-aziridin-2-yl)-ketone 
• 14367-97-6 1-(4-bromophenyl)-2-nitro-1-ethanone 

Downstream Products

• 370598-02-0 4-(2-phenyl-oxazol-5-yl)-benzenesulfonyl chloride 

Relevant articles and documents

Metal-free iodine(iii)-promoted synthesis of 2,5-diaryloxazoles

A nonmetal-catalyzed oxidative cyclization to achieve 2,5-disubstituted oxazoles from inexpensive and readily available substituted chalcone, (diacetoxyiodo)benzene (PIDA) and ammonium acetate (NH4OAc) at room temperature is described. The reaction forms a variety of 2,5-diaryloxazoles in good to excellent yields with broad substrate scope under mild conditions without the requirement of ligands and additional bases.

N -Bromosuccinimide as a Brominating Agent for the Transformation of N -H (or N -Benzyl) Ketoaziridines into Oxazoles

A novel procedure for the direct synthesis of 2,5-diaryloxazoles starting from N-H ketoaziridines is described. The method proceeds via the in situ formation of N-bromoketoaziridines in the presence of N-bromosuccinimide followed by the generation of intermediate azomethine ylides. A plausible mechanism for this transformation is proposed.

Reaction of alkynes and azides: Not triazoles through copper-acetylides but oxazoles through copper-nitrene intermediates

Well-defined copper(I) complexes of composition [Tpm* ,BrCu(NCMe)]BF4 (Tpm*,Br=tris(3,5- dimethyl-4-bromo-pyrazolyl)methane) or [Tpa* Cu]PF6 (Tpa=tris(3,5-dimethyl-pyrazolylmethyl)amine) catalyze the formation of 2,5-disubstituted oxazoles from carbonyl azides and terminal alkynes in a direct manner. This process represents a novel procedure for the synthesis of this valuable heterocycle from readily available starting materials, leading exclusively to the 2,5-isomer, attesting to a completely regioselective transformation. Experimental evidence and computational studies have allowed the proposal of a reaction mechanism based on the initial formation of a copper-acyl nitrene species, in contrast to the well-known mechanism for the copper-catalyzed alkyne and azide cycloaddition reactions (CuAAC) that is triggered by the formation of a copper-acetylide complex.