201282-63-5

Basic information

• Product Name: 1,2,3-OxadiazoliuM, 5-hydroxy-4-iodo-3-(4-Methoxyphenyl)-, inner salt
• Synonyms: 1,2,3-OxadiazoliuM, 5-hydroxy-4-iodo-3-(4-Methoxyphenyl)-, inner salt
• CAS NO: 201282-63-5
• Molecular Formula: C9H9IN2O3
• Molecular Weight: 320.08383
• EINECS: -0
• Mol File: 201282-63-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,2,3-OxadiazoliuM, 5-hydroxy-4-iodo-3-(4-Methoxyphenyl)-, inner salt(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3-OxadiazoliuM, 5-hydroxy-4-iodo-3-(4-Methoxyphenyl)-, inner salt(201282-63-5)
• EPA Substance Registry System: 1,2,3-OxadiazoliuM, 5-hydroxy-4-iodo-3-(4-Methoxyphenyl)-, inner salt(201282-63-5)

Safety Data

• Hazardous Substances Data: 201282-63-5(Hazardous Substances Data)

Upstream product

• 3815-80-3 3-(p-anisyl)sydnone 
• 104-94-9 4-methoxy-aniline 
• 50845-77-7 N-(4-methoxy)phenylglycine ethyl ester 

Downstream Products

• 1205123-39-2 5-iodo-1-(4-methoxyphenyl)-3-phenyl-1H-pyrazole 
• 1429485-53-9 4-trifluoromethyl-N-(p-methoxyphenyl)-sydnone 
• 1429485-75-5 1-(4-methoxyphenyl)-3-phenyl-5-(trifluoromethyl)-1H-pyrazole 
• 1429485-77-7 1-(p-methoxyphenyl)-3-n-butyl-5-trifluoromethyl-1H-pyrazole 
• 1429485-79-9 1-(p-methoxyphenyl)-3-cyclopropyl-5-trifluoromethyl-1H-pyrazole 
• 1429486-35-0 1-(4-methoxy-3-nitrophenyl)-3-phenyl-5-trifluoromethyl-1H-pyrazole 

Relevant articles and documents

Discovery of Fluorogenic Diarylsydnone-Alkene Photoligation: Conversion of ortho-Dual-Twisted Diarylsydnones into Planar Pyrazolines

A small library of diarylsydnones (DASyds) was constructed based on aryl-pairing combinations and subjected to click reaction toward alkenes under photoirradiation with high efficiency. We were able to demonstrate the utility of DASyds for highly fluorescent turn-on ligation targeting the trans-cyclooct-4-en-1-ol moieties on protein.

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.

Improved method for the iodination of sydnones

Iodination at the sydnone C-4 position has been achieved in good yields for a series of 3-arylsydnones using N-iodosuccinimide in acetic acid. Taylor & Francis Group, LLC.

Facile access to 3,5-dihalogenated pyrazoles by sydnone cycloaddition and their versatile functionalization by Pd-catalyzed cross-coupling processes

The 1,3-dipolar cycloaddition of diversely N-substituted 4-iodosydnones with 3-halopropiolates produces easily separable mixtures of dihalogenated pyrazolylcarboxylic esters at a preparative scale level, with the 3,5-dihalogenopyrazole regioisomers always predominating. Further decarboxylation of the major isomers provided the corresponding 3,5-dihalogenopyrazoles with a free C-4 position. These were found to be valuable scaffolds for the elaboration of unsymmetrically 1,3,5-trisubstituted pyrazole derivatives by site-selective Pd-catalyzed cross-coupling reactions. Notably, the flexible and site-selective introduction of different (hetero)aryl, vinyl, or alkyl substituents at the C-5 and C-3 positions of the pyrazole core could be achieved through sequential Suzuki-type reactions with various boron compounds. Copyright

Alkyne [3 + 2] cycloadditions of iodosydnones toward functionalized 1,3,5-trisubstituted pyrazoles

(Chemical Equation Presented) The cycloaddition of 4-iodosydnones with terminal alkynes proceeds with excellent regiocontrol to provide 5-iodo pyrazoles. These products participate smoothly in subsequent C-C and C-heteroatom bond forming processes.