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

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 
• 103-01-5 N-Phenylglycine 
• 6415-68-5 N-nitroso-N-phenylglycine 

Downstream Products

• 70428-84-1 3-Bromo-2-cyano-3-(N'-dicyanomethylene-N-phenyl-hydrazino)-acrylonitrile 
• 34731-93-6 3-Phenyl-4-(triethylsilyl)sydnon 
• 34740-31-3 4-(Pentamethyldisilanyl)-3-phenylsydnon 
• 34740-32-4 1,1,2,2-Tetramethyl-1,2-bis(3-phenyl-4-sydnonyl)disilan 
• 16796-23-9 phenylbis(3-phenyl-4-sydnonyl)methanol 
• 34740-30-2 3-phenyl-4-trimethylsilanyl-sydnone 
• 508191-77-3 3-phenylsydnone 
• 5319-54-0 4-(anilino-morpholin-4-yl-acetyl)-morpholine 
• 16796-28-4 bis(3-phenyl-4-sydnonyl)sulfide 
• 109411-37-2 4-(α-hydroxy-benzyl)-3-phenyl-sydnone 
• 37429-52-0 4-(1-hydroxy-1-methyl-ethyl)-3-phenyl-sydnone 
• 13183-08-9 4-carboxy-3-phenyl-sydnone 
• 13973-33-6 4-acetyl-3-phenylsydnone 
• 13858-07-6 4-iodo-3-phenyl-1,2,3-λ⁵-oxadiazol-3-ium-5-olate 

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.

Anionic N-heterocyclic carbenes by decarboxylation of sydnone-4-carboxylates

Unstable N-heterocyclic carbenes can be masked and stabilized as pseudo-cross-conjugated hetarenium-carboxylates which decarboxylate on warming. This study deals with the decarboxylation of carboxylates of mesoionic compounds to generate anionic N-heteroc

Bioorthogonal Click and Release Reaction of Iminosydnones with Cycloalkynes

We report the discovery of a new bioorthogonal click-and-release reaction involving iminosydnones and strained alkynes. This transformation leads to two products resulting from the ligation and fragmentation of iminosydnones under physiological conditions. Optimized iminosydnones were successfully used to design innovative cleavable linkers for protein modification, thus opening up new areas in the fields of drug release and target-fishing applications. This click-and-release technology offers the possibility of exchanging tags on proteins for functionalized cyclooctynes under mild and bioorthogonal conditions.

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

4-Halogeno-sydnones for fast strain promoted cycloaddition with bicyclo-[6.1.0]-nonyne

New sydnone derivatives have been synthesized and screened for their capacity to undergo fast copper-free cycloaddition reaction with bicyclo-[6.1.0]-nonyne. The influences of substitution in positions N-3 and C-4 of sydnones have been particularly studied leading to the identification of highly reactive partners for bio-orthogonal ligation reactions.

Cross coupling of bromo sydnones: Development of a flexible route toward functionalized pyrazoles

(Chemical Equation Presented) The application of a Suzuki cross coupling approach to a range of C-4 substituted sydnones from a 4-bromosydnone is described. Moreover, the potential of this approach to prepare a diverse range of pyrazoles is demonstrated.

Catalytic activity of 1,3-dibromo-5,5-dimethylhydantoin (DBH) in the one-pot transformation of N-arylglycines to N-arylsydnones in the presence of NaNO2/Ac2O under neutral conditions: Subsequent bromination of these sydnones to their

1,3-Dibromo-5,5-dimethylhydantoin (DBH) has been found to efficiently catalyze the one-pot conversion of various N-arylglycines through N-nitrosation and cyclization to sydnones in combination with NaNO2 and Ac 2O in high yields (80-

Transformation of the sydnone ring into oxadiazolinones. A convenient one-pot synthesis of 3-aryl-5-methyl-1,3,4-oxadiazolin-2-ones from 3- arylsydnones and their antimicrobial activity

3-Arylsydnones (Ia-u) have been converted into the corresponding 3-aryl- 5-methyl-1,3,4-oxadiazolin-2-ones (IIIa-u) by a single-step reaction with bromine in acetic anhydride. In the preliminary screening of all these compounds, the halogen-substituted de