3483-19-0

Basic information

• Product Name: 1,2,3-OxadiazoliuM, 5-hydroxy-3-(4-Methylphenyl)-, inner salt
• Synonyms: 1,2,3-OxadiazoliuM, 5-hydroxy-3-(4-Methylphenyl)-, inner salt
• CAS NO: 3483-19-0
• Molecular Formula: C₉H₈N₂O₂
• Molecular Weight: 178.1879
• EINECS: -0
• Mol File: 3483-19-0.mol
• Article Data: 19

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• CAS DataBase Reference: 1,2,3-OxadiazoliuM, 5-hydroxy-3-(4-Methylphenyl)-, inner salt(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3-OxadiazoliuM, 5-hydroxy-3-(4-Methylphenyl)-, inner salt(3483-19-0)
• EPA Substance Registry System: 1,2,3-OxadiazoliuM, 5-hydroxy-3-(4-Methylphenyl)-, inner salt(3483-19-0)

Safety Data

• Hazardous Substances Data: 3483-19-0(Hazardous Substances Data)

Usage

Type of Compound

Oxadiazolium derivative

Functional Groups

Oxadiazolium ring
Hydroxy group
4-Methylphenyl substituent

Potential Applications

Pharmaceutical industry
Medicinal chemistry

Biological Activity

Antimicrobial properties
Antioxidant properties

Structure Significance

The oxadiazolium ring provides a stable and versatile chemical framework
The hydroxy group allows for hydrogen bonding and increased solubility
The 4-Methylphenyl substituent introduces steric hindrance and electronic effects, potentially influencing the compound's biological activity

Research and Development

Valuable for exploring new drug candidates
Contributes to the advancement of pharmaceutical chemistry

Inner Salt

Indicates the presence of a charged species within the molecule, which can affect its reactivity and interactions with other molecules.

InChI:InChI=1/C9H8N2O2/c1-7-2-4-8(5-3-7)11-6-9(12)13-10-11/h2-6H,1H3

Upstream product

• 52827-02-8 2-(nitroso(p-tolyl)amino)acetic acid 
• 21911-69-3 N-(p-tolyl)glycine 
• 106-49-0 p-toluidine 
• 21911-68-2 ethyl 2-(p-tolylamino)acetate 
• 106-38-7 para-bromotoluene 

Downstream Products

• 68657-36-3 alpha-(2-(2,2-dicyanovinyl)-2-(p-tolyl)hydrazono)malononitrile 
• 21977-61-7 3-(4-methyl-3-nitro-phenyl)-sydnone 
• 4918-23-4 4-bromo-3-p-tolyl-sydnone 
• 60642-50-4 bis<3-(p-tolyl)-4-sydnonyl>sulfide 
• 98700-47-1 1-(4-Methylphenyl)-1H-pyrazole-3-carbaldehyde 
• 98700-46-0 3-(4-Fluorophenylimino)methyl-1-(4-methylphenyl)-1H-pyrazole 
• 98700-45-9 3-(4-Fluorophenylimino)methyl-4,5-dihydro-1-(4-methylphenyl)-5-morpholino-1H-pyrazole 
• 78702-49-5 4-(chlorosulfonyl)-3-(p-tolyl)sydnone 
• 72913-08-7 4-acetyl-3-(4-methylphenyl)sydnone 
• 3815-76-7 4-chloro-3-(4-tolyl)sydnone 
• 637-60-5 p-tolylhydrazine hydrochloride 
• 86870-31-7 4-(4-carboxyphenylhydrazono)methyl-3-(4-methylphenyl)sydnone 
• 23875-86-7 dimethyl 1-(p-tolyl)-1H-pyrazol-3,4-dicarboxylate 
• 76242-34-7 4-bromoacetyl-3-(4-methylphenyl)sydnone 

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.

Novel sydnone derivatives carrying azidomethyl-1,2, 4-oxadiazole unit and their 1,3-dipolar cycloadditions

A series of 1,2,4-oxadiazolymethyl sydnones carrying azido group were synthesized and subjected to react with a variety of alkenic and acetylenic dipolarophilic reagents; N-phenyl maleimide, phenyl vinyl sulfone, and phenyl propiolic acid. All the new products are identified by spectral/physical data including high-resolution mass measurements and X-ray diffraction data.

Ultrafast Click Chemistry with Fluorosydnones

We report the synthesis and reactivity of 4-fluorosydnones, a unique class of mesoionic dipoles displaying exquisite reactivity towards both copper-catalyzed and strain-promoted cycloaddition reactions with alkynes. Synthetic access to these new mesoionic compounds was granted by electrophilic fluorination of σ-sydnone PdIIprecursors in the presence of Selectfluor. Their reactions with terminal and cyclic alkynes were found to proceed very rapidly and selectively, affording 5-fluoro-1,4-pyrazoles with bimolecular rate constants up to 104m?1s?1, surpassing those documented in the literature with cycloalkynes. Kinetic studies were carried out to unravel the mechanism of the reaction, and the value of 4-fluorosydnones was further highlighted by successful radiolabeling with [18F]Selectfluor.