508191-77-3

Basic information

• Product Name: 1,2,3-Oxadiazolium,2,5-dihydro-5-oxo-3-phenyl-,innersalt(9CI)
• Synonyms: 1,2,3-Oxadiazolium,2,5-dihydro-5-oxo-3-phenyl-,innersalt(9CI)
• CAS NO: 508191-77-3
• Molecular Formula: C₈H₆N₂O₂
• Molecular Weight: 163.15338
• Product Categories: AMINESECONDARY
• Mol File: 508191-77-3.mol
• Article Data: 33

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,2,3-Oxadiazolium,2,5-dihydro-5-oxo-3-phenyl-,innersalt(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3-Oxadiazolium,2,5-dihydro-5-oxo-3-phenyl-,innersalt(9CI)(508191-77-3)
• EPA Substance Registry System: 1,2,3-Oxadiazolium,2,5-dihydro-5-oxo-3-phenyl-,innersalt(9CI)(508191-77-3)

Safety Data

• Hazardous Substances Data: 508191-77-3(Hazardous Substances Data)

Usage

Chemical class

Heterocyclic compound

Explanation

Different sources of media describe the Explanation of 508191-77-3 differently. You can refer to the following data:
1. It is a compound with a ring structure containing oxygen and nitrogen atoms.
2. The oxadiazole ring consists of five atoms.
3. The compound has an oxadiazolium group and a phenyl group attached to the ring.
4. The compound is named according to the 9CI nomenclature system, which is a systematic method for naming organic compounds.
5. The compound has a positive charge on the oxadiazolium ring and a negative charge on the adjacent atom, forming an innersalt.
6. Due to its unique chemical structure, the compound may have applications in the development of drugs and agrochemicals.
7. Further research is being conducted to explore the properties and potential uses of this compound in various industries.
8. The compound has a dihydro (two hydrogen atoms) and a keto (carbonyl group) functional group at the 5-position, and a phenyl group at the 3-position of the oxadiazolium ring.
9. The molecular formula is not given in the material provided, but it can be inferred that it contains carbon, hydrogen, oxygen, and nitrogen atoms.
10. The stability of the compound is not mentioned in the material provided, but it is an important factor to consider when evaluating its potential applications.

Ring structure

Five-membered

Functional groups

Oxadiazolium and phenyl

Nomenclature

9CI

Innersalt

Exists as an innersalt

Applications

Potential use in pharmaceuticals and agrochemicals

Research status

Ongoing

Chemical structure

2,5-dihydro-5-oxo-3-phenyl

Stability

Not specified

Upstream product

• 108-24-7 acetic anhydride 
• 6415-68-5 N-nitroso-N-phenylglycine 
• 13973-33-6 4-acetyl-3-phenylsydnone 
• 62-53-3 aniline 
• 108-86-1 bromobenzene 
• 2216-92-4 N-phenylglycine ethyl ester 
• 51126-04-6 4-bromoacetyl-3-phenylsydnone 
• 103-01-5 N-Phenylglycine 
• 14484-83-4 4-formyl-3-phenyl-sydnone 
• 13183-09-0 3-phenyl-4-bromosydnone 
• 75-77-4 chloro-trimethyl-silane 
• 51126-13-7 1-[2-oxo-2-(5-oxo-3-phenyl-2,5-dihydro-[1,2,3]oxadiazolium-4-yl)-ethyl]-pyridinium; bromide 

Downstream Products

• 1666-85-9 1,3,4-triphenyl-1H-pyrazole 
• 19307-52-9 3-benzo[1,3]dioxol-5-ylmethyl-1-phenyl-4,5-dihydro-1H-pyrazole 
• 29179-68-8 4-(methylsulfanyl)-3-phenyl-1,2,3-oxadiazol-3-ium-5-olate 
• 38532-40-0 4-(1-hydroxy-1-methyl-butyl)-3-phenyl-sydnone 
• 13973-35-8 4-propanoyl-3-phenylsydnone 
• 69163-19-5 4-(4-nitrophenyl)-3-phenyl-1,2,3-oxadiazol-3-ium-5-olate 
• 34740-30-2 3-phenyl-4-trimethylsilanyl-sydnone 
• 3815-83-6 3,4-diphenylsydnone 
• 122682-48-8 4-(4-methoxyphenyl)-3-phenyl-1,2,3-oxadiazol-3-ium-5-olate 
• 105786-84-3 1,4-dihydro-4-isopropylidene-1-phenyl-5H-1,2-diazepin-5-one 
• 109123-09-3 3-tert-Butyl-1-phenyl-1H-1,2,4-diazaphosphol 
• 110256-51-4 1,3-Diphenyl-1H-[1,2,4]diazaphosphole 
• 137046-53-8 (Z)-1-Phenylpyrazolo<3,4-c>-bicyclo<4.4.1>undeca-3,6,8,10-tetraen-2,5-dion-2-(4-nitrophenyl)hydrazon 
• 137046-54-9 (E)-1-Phenylpyrazolo<3,4,-g>-tricyclo<4.4.1.0^1.6>undeca-3,7,9-trien-2,5-dion-2-N-methyl-(4-nitrophenyl)hydrazon 

Relevant articles and documents

Water-Involved Ring-Opening of 4-Phenyl-1,2,4-triazoline-3,5-dione for “Photo-Clicked” Access to Carbamoyl Formazan Photoswitches In Situ

Cyclic azodicarbonyl derivatives, particularly 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD), commonly serve as arenophile, dienophile, enophile and electrophile. Perplexed by its instability in aqueous environment, there are few studies focused on the transient intermediate produced by hydrolysis of PTAD to achieve synthetic significance. Herein, we describe a “photo-click” method that involves nitrile imine (NI) from diarylsydnone to capture the diazenecarbonyl-phenyl-carbamic acid (DACPA) generated by water-promoted ring-opening of PTAD. DFT calculation reveal that H-bonding interactions between PTAD and water are vital to form DACPA which exhibited an umpolung effect during ligation by nature bond orbit (NBO) analysis. The ultra-fast ligation resulted in carbamoyl formazans, as a unique Z?E photo-switchable linker on target molecules, including peptide and drugs, with excellent anti-fatigue performance. This strategy is showcased to construct highly functionalized carbamoyl formazans in situ for photo-pharmacology and material studies, which also expands the chemistry of PTAD in aqueous media.

Mechanosynthesis of sydnone-containing coordination complexes

N-Phenyl-4-(2-pyridinyl) sydnone was shown to act as a four-electron donor N,O-ligand in unprecedented coordination complexes featuring three different metallic centers (Co, Cu, and Zn). Starting with various anilines, the use of a ball-mill efficiently enabled the synthesis of N-arylglycines, subsequent nitrosylation and cyclization into sydnones, and further metalation.

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.