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

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.

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.

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.

Synthesis, anti-bacterial, and anti-fungal activity of sydnone-based aromatic compounds

In order to investigate the biological importance of sydnone ring system, two new series viz. 4-(N-(4-(3-(substitutedphenyl)acryloyl) phenyl) sulfamoyl)-3-p-tolyl-sydnone (Series-A) and 4-(N-(4-(5-(substitutedphenyl)isoxazol-3-yl)phenyl)4-sulfamoyl)-3-p-t

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.

One-pot synthesis of 1,4-disubstituted pyrazoles from arylglycines via copper-catalyzed sydnone-alkyne cycloaddition reaction

A robust method for constructing 1,4-pyrazoles from arylglycines was developed using the copper-catalyzed sydnone-alkyne cycloaddition reaction. The procedure offers a straightforward and general route to the pyrazole heterocycle through a three-step one-pot procedure.

Regioselective reaction: Synthesis, characterization and pharmacological activity of some new Mannich and Schiff bases containing sydnone

A novel series of 1-substituted aminomethyl-3-[1-(4-isobutylphenyl)ethyl]- 4-(3-aryl-4-sydnonylidene) amino-1,2,4-triazol-5-thiones (9), was prepared from the 3-[1-(4-isobutylphenyl)ethyl]-4-(3-aryl-4-sydnonylidene) amino 5-mercapto-1,2,4-triazoles (8) by aminomethylation with formaldehyde and secondary amine. The structures of Schiff bases (8) and Mannich bases (9) were characterized on the basis of IR, NMR, mass spectra1 data and elemental analysis. The newly synthesized compounds were screened for their anti-inflammatory and analgesic activities. Mannich bases (9) carrying piperidine and morpholine residues showed promising anti-inflammatory and analgesic activity.

Synthesis of 2 H-indazoles by the [3 + 2] dipolar cycloaddition of sydnones with arynes

A rapid and efficient synthesis of 2H-indazoles has been developed using a [3 + 2] dipolar cycloaddition of sydnones and arynes. A series of 2H-indazoles have been prepared in good to excellent yields using this protocol, and subsequent Pd-catalyzed coupl