1310070-02-0

Basic information

• Product Name: (4-methoxyphenyl)(4-nitrophenyl)iodonium p-toluenesulfonate
• Synonyms: (4-methoxyphenyl)(4-nitrophenyl)iodonium p-toluenesulfonate
• CAS NO: 1310070-02-0
• Molecular Weight: 527.337
• Mol File: 1310070-02-0.mol

Chemical Properties

• CAS DataBase Reference: (4-methoxyphenyl)(4-nitrophenyl)iodonium p-toluenesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: (4-methoxyphenyl)(4-nitrophenyl)iodonium p-toluenesulfonate(1310070-02-0)
• EPA Substance Registry System: (4-methoxyphenyl)(4-nitrophenyl)iodonium p-toluenesulfonate(1310070-02-0)

Safety Data

• Hazardous Substances Data: 1310070-02-0(Hazardous Substances Data)

Upstream product

• 636-98-6 p-nitrobenzene iodide 
• 104-15-4 toluene-4-sulfonic acid 
• 100-66-3 methoxybenzene 
• 73178-10-6 4-nitrobenzene 

Downstream Products

• 959-22-8 p-nitrophenylbenzoate 
• 133622-64-7 4-[¹²⁵I]iodonitrobenzene 
• 22865-50-5 4-(4-methoxyphenylsulfanyl)nitrobenzene 
• 501680-99-5 4-nitro-N-(3-phenylpropyl)aniline 
• 909713-18-4 (S)-methyl 2-(4-methoxyphenylamino)-3-phenylpropanoate 
• 10252-51-4 1-(4-nitrophenyl)-3,5-diphenyl-1H-pyrazole 
• 102183-30-2 1,2,5-tri-(4-nitrophenyl)-1H-pyrazole 
• 58750-95-1 4-methyl-N-(4-nitrophenyl)-N-phenylbenzenesulfonamide 
• 432-87-1 1-nitro-4-(trifluoromethylsulfonyl)benzene 
• 15183-74-1 1-methoxy-4-((trifluoromethyl)sulfonyl)benzene 

Relevant articles and documents

Transition Metal-Free N-Arylation of Amino Acid Esters with Diaryliodonium Salts

A transition metal-free approach for the N-arylation of amino acid derivatives has been developed. Key to this method is the use of unsymmetric diaryliodonium salts with anisyl ligands, which proved important to obtain high chemoselectivity and yields. The scope includes the transfer of both electron deficient, electron rich and sterically hindered aryl groups with a variety of different functional groups. Furthermore, a cyclic diaryliodonium salt was successfully employed in the arylation. The N-arylated products were obtained with retained enantiomeric excess.

METHOD FOR SYNTHESIZING IODO- OR ASTATOARENES USING DIARYLIODONIUM SALTS

The present invention concerns a method of synthesizing a iodo- or astatoarene comprising the reaction of a diaryliodonium compound with a iodide or astatide salt, respectively. The invention also relates to said iodo- or astatoarene and diaryliodonium co

Unexpected Behavior of the Heaviest Halogen Astatine in the Nucleophilic Substitution of Aryliodonium Salts

Aryliodonium salts have become precursors of choice for the synthesis of18F-labeled tracers for nuclear imaging. However, little is known on the reactivity of these compounds with heavy halides, that is, radioiodide and astatide, at the radiotracer scale. In the first comparative study of radiohalogenation of aryliodonium salts with125I?and211At?, initial experiments on a model compound highlight the higher reactivity of astatide compared to iodide, which could not be anticipated from the trends previously observed within the halogen series. Kinetic studies indicate a significant difference in activation energy (Ea=23.5 and 17.1 kcal mol?1with125I?and211At?, respectively). Quantum chemical calculations suggest that astatination occurs via the monomeric form of an iodonium complex whereas iodination occurs via a heterodimeric iodonium intermediate. The good to excellent regioselectivity of halogenation and high yields achieved with diversely substituted aryliodonium salts indicate that this class of compounds is a promising alternative to the stannane chemistry currently used for heavy radiohalogen labeling of tracers in nuclear medicine.

Transition-Metal-Free N-Arylation of Pyrazoles with Diaryliodonium Salts

A new synthetic method was developed for the N-arylation of pyrazoles using diaryliodonium salts. The transformation does not require any transition-metal catalyst and provides the desired N-arylpyrazoles rapidly under mild reaction condition in the presence of aqueous ammonia solution as a mild base without the use of inert atmosphere. The chemoselectivity of unsymmetric diaryliodonium salts was also explored with large number of examples.

Metal-free arylation of oxygen nucleophiles with diaryliodonium salts

Phenols and carboxylic acids are efficiently arylated with diaryliodonium salts. The reaction conditions are mild, metal free, and avoid the use of halogenated solvents, additives, and excess reagents. The products are obtained in good-to-excellent yields after short reaction times. Steric hindrance is very well tolerated, both in the nucleophile and diaryliodonium salt. The scope includes ortho- and halo-substituted products, which are difficult to obtain by metal-catalyzed protocols. Many functional groups are tolerated, including carbonyl groups, heteroatoms, and alkenes. Unsymmetric salts can be chemoselectively utilized to obtain products with hitherto unreported levels of steric congestion. The arylation has been extended to sulfonic acids, which can be converted to sulfonate esters by two different approaches. With recent advances in efficient synthetic procedures for diaryliodonium salts the reagents are now inexpensive and readily available. The iodoarene byproduct formed from the iodonium reagent can be recovered quantitatively and used to regenerate the diaryliodonium salt, which improves the atom economy. Copyright

Metal-free synthesis of aryl esters from carboxylic acids and diaryliodonium salts

An efficient arylation of carboxylic acids with diaryliodonium salts has been developed, giving aryl esters in high yields within short reaction times for both aromatic and aliphatic substrates. The transition-metal-free conditions are compatible with a range of functional groups, and good chemoselectivity is observed with unsymmetric diaryliodonium salts. Furthermore, steric hindrance in the ortho positions is well tolerated both in the carboxylic acid and in the diaryliodonium salt, yielding aryl esters that cannot be obtained via other esterification protocols.