13183-09-0

Basic information

• Product Name: 4-bromo-3-phenyl-1,2,3-oxadiazol-3-ium-5-olate
• Synonyms: 1,2,3-oxadiazolium, 4-bromo-5-hydroxy-3-phenyl-, inner salt; 4-Bromo-3-phenyl-1,2,3-oxadiazol-3-ium-5-olate
• CAS NO: 13183-09-0
• Molecular Formula: C₈H₅BrN₂O₂
• Molecular Weight: 241.0415
• Mol File: 13183-09-0.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: 4-bromo-3-phenyl-1,2,3-oxadiazol-3-ium-5-olate(CAS DataBase Reference)
• NIST Chemistry Reference: 4-bromo-3-phenyl-1,2,3-oxadiazol-3-ium-5-olate(13183-09-0)
• EPA Substance Registry System: 4-bromo-3-phenyl-1,2,3-oxadiazol-3-ium-5-olate(13183-09-0)

Safety Data

• Hazardous Substances Data: 13183-09-0(Hazardous Substances Data)

Upstream product

• 508191-77-3 3-phenylsydnone 
• 6415-68-5 N-nitroso-N-phenylglycine 
• 103-01-5 N-Phenylglycine 

Downstream Products

• 5319-54-0 4-(anilino-morpholin-4-yl-acetyl)-morpholine 
• 70428-84-1 3-Bromo-2-cyano-3-(N'-dicyanomethylene-N-phenyl-hydrazino)-acrylonitrile 
• 34740-32-4 1,1,2,2-Tetramethyl-1,2-bis(3-phenyl-4-sydnonyl)disilan 
• 16796-22-8 3,3'-diphenyl-4,4'-(1-hydroxy-pentane-1,1-diyl)-bis-sydnone 
• 34740-31-3 4-(Pentamethyldisilanyl)-3-phenylsydnon 
• 508191-77-3 3-phenylsydnone 
• 28740-63-8 5-methyl-3-phenyl-1,3,4-oxadiazol-2(3H)-one 

Relevant articles and documents

The reaction of sydnones with bromine in acetic anhydride revisited: A new route to 5-substituted-3-aryl-1,3,4-oxadiazol-2(3H)-ones from N-aryl-N-bromocarbonylhydrazines

The reaction of 3-phenylsydnone with bromine in acetic anhydride to form 5-methyl-3-phenyl-1,3,4-oxadiazol-2(3H)-one has been reexamined and improved. A new mechanism involving a bromocarbonylhydrazine species is proposed and its intermediacy is supported

Sydnone Reporters for Highly Fluorogenic Copper-Free Click Ligations

Bioorthogonal fluorescent turn-on reactions are attractive for the sensitive real-time detection of a variety of phenomena including bioconjugation, chemical reactivity, and material assembly. Herein we describe the use of 3,4-disubstituted sydnones, a singular class of mesoionic dipoles, for highly fluorescent turn-on copper-free click cycloadditions with the fluorogenic dibenzocyclooctyne Fl-DIBO. Coherent with time-dependent density functional theory calculations, the pyrazole cycloadducts were found to be highly fluorescent with compelling photophysical properties including excellent fluorescence enhancement (up to 240-fold), high quantum yields (over 45%), and large Stokes shift (over 100 nm). Furthermore, the good stability and reactivity of 4-chlorosydnones with Fl-DIBO allowed us to employ them as chemical reporters for the challenging detection of modified-proteins in complex cellular extracts, with exquisite specificity in no-wash conditions. This novel fluorogenic system significantly expands our chemical biology toolbox and should be beneficial in countless applications.

Copper(I)-catalyzed cycloaddition of 4-bromosydnones and alkynes for the regioselective synthesis of 1,4,5-trisubstituted pyrazoles

Copper-catalyzed cycloaddition of alkynes with 4-bromosydnones provides a convenient, mild, and regioselective method for the synthesis of a wide range of bromopyrazoles. The broad functional group tolerance of the cycloaddition reaction and further palla