905718-45-8

Basic information

• Product Name: (4-Nitrophenyl)phenyliodonium trifluoromethanesulfonate
• Synonyms: (4-Nitrophenyl)phenyliodonium trifluoromethanesulfonate
• CAS NO: 905718-45-8
• Molecular Formula: CF₃O₃S*C₁₂H₉INO₂
• Molecular Weight: 475.1789396
• Mol File: 905718-45-8.mol
• Article Data: 7

Chemical Properties

• Melting Point: 198.0 to 202.0 °C
• Appearance: /
• Solubility: soluble in Methanol
• BRN: 10500170
• CAS DataBase Reference: (4-Nitrophenyl)phenyliodonium trifluoromethanesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: (4-Nitrophenyl)phenyliodonium trifluoromethanesulfonate(905718-45-8)
• EPA Substance Registry System: (4-Nitrophenyl)phenyliodonium trifluoromethanesulfonate(905718-45-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 905718-45-8(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(4-Nitrophenyl)phenyliodonium trifluoromethanesulfonate is used as a reagent for oxidative transformations and as a source of electrophilic aromatic iodine species. It is particularly useful for its mild and selective reactivity in organic synthesis processes.
Used in Pharmaceutical and Agrochemical Synthesis:
(4-Nitrophenyl)phenyliodonium trifluoromethanesulfonate is employed in the synthesis of various pharmaceuticals and agrochemicals. Its ability to facilitate carbon-carbon and carbon-heteroatom bond formations makes it a versatile reagent in these industries.

Upstream product

• 591-50-4 iodobenzene 
• 1493-13-6 trifluorormethanesulfonic acid 
• 98-95-3 nitrobenzene 
• 35895-70-6 tetrabutylammonium trifluoromethylsulfonate 
• 636-98-6 p-nitrobenzene iodide 
• 98-80-6 phenylboronic acid 
• 2926-30-9 sodium triflate 
• 71-43-2 benzene 

Downstream Products

• 224184-25-2 1-(4-nitrophenyl)-3-benzyl-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one 
• 35895-70-6 tetrabutylammonium trifluoromethylsulfonate 
• 104226-37-1 N-benzyl-N-methyl-4-nitroaniline 

Relevant articles and documents

Palladium(ii)-catalyzed stereoselective synthesis of: C-glycosides from glycals with diaryliodonium salts

An efficient palladium(ii) mediated C-glycosylation of glycals with diaryliodonium salts is described, providing a new strategy for the synthesis of 2,3-dideoxy C-Aryl glycosides with excellent stereoselectivity. The C-glycosylation of a diverse range of

Lewis Acidity Scale of Diaryliodonium Ions toward Oxygen, Nitrogen, and Halogen Lewis Bases

Equilibrium constants for the associations of 17 diaryliodonium salts Ar2I+X- with 11 different Lewis bases (halide ions, carboxylates, p-nitrophenolate, amines, and tris(p-anisyl)phosphine) have been investigated by titrations followed by photometric or conductometric methods as well as by isothermal titration calorimetry (ITC) in acetonitrile at 20 °C. The resulting set of equilibrium constants KI covers 6 orders of magnitude and can be expressed by the linear free-energy relationship lg KI = sI LAI + LBI, which characterizes iodonium ions by the Lewis acidity parameter LAI, as well as the iodonium-specific affinities of Lewis bases by the Lewis basicity parameter LBI and the susceptibility sI. Least squares minimization with the definition LAI = 0 for Ph2I+ and sI = 1.00 for the benzoate ion provides Lewis acidities LAI for 17 iodonium ions and Lewis basicities LBI and sI for 10 Lewis bases. The lack of a general correlation between the Lewis basicities LBI (with respect to Ar2I+) and LB (with respect to Ar2CH+) indicates that different factors control the thermodynamics of Lewis adduct formation for iodonium ions and carbenium ions. Analysis of temperature-dependent equilibrium measurements as well as ITC experiments reveal a large entropic contribution to the observed Gibbs reaction energies for the Lewis adduct formations from iodonium ions and Lewis bases originating from solvation effects. The kinetics of the benzoate transfer from the bis(4-dimethylamino)-substituted benzhydryl benzoate Ar2CH-OBz to the phenyl(perfluorophenyl)iodonium ion was found to follow a first-order rate law. The first-order rate constant kobs was not affected by the concentration of Ph(C6F5)I+ indicating that the benzoate release from Ar2CH-OBz proceeds via an unassisted SN1-type mechanism followed by interception of the released benzoate ions by Ph(C6F5)I+ ions.

Metal-Free C-Arylation of Nitro Compounds with Diaryliodonium Salts

An efficient, mild, and metal-free arylation of nitroalkanes with diaryliodonium salts has been developed, giving easy access to tertiary nitro compounds. The reaction proceeds in high yields without the need for excess reagents and can be extended to α-arylation of nitroesters. Nitroalkanes were selectively C-arylated in the presence of other easily arylated functional groups, such as phenols and aliphatic alcohols.

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

Reaction of iodoarenes with potassium peroxodisulfate/trifluoroacetic acid in the presence of aromatics. Direct preparation of diaryliodonium triflates from iodoarenes

Diaryliodonium triflates have been directly prepared by reaction of some iodoarenes with aromatic substrates in good yields by using K2S2O8/CF3COOH/CH2Cl2. Treatment of a variety of iodoare

Novel anthracene derivative and radiation-sensitive resin composition

A novel anthracene derivative useful as an additive to a radiation-sensitive resin composition is disclosed. The anthracene derivative has the following formula (1), wherein R1 groups individually represent a hydroxyl group or a monovalent organic group having 1-20 carbon atoms, n is an integer of 0-9, X is a single bond or a divalent organic group having 1-12 carbon atoms, and R2 represents a monovalent acid-dissociable group. The radiation-sensitive resin composition comprises the anthracene derivative of the formula (1), a resin insoluble or scarcely soluble in alkali, but becomes alkali soluble in the presence of an acid, and a photoacid generator. The composition is useful as a chemically-amplified resist for microfabrication utilizing deep ultraviolet rays, typified by a KrF excimer laser and ArF excimer laser.

Novel carbazole derivative and chemically amplified radiation-sensitive resin composition

A carbazole derivative of the following formula (1), wherein R1 and R2 individually represent a hydrogen atom or a monovalent organic group, or R1 and R2 form, together with the carbon atom to which R1 and R2 bond, a divalent organic group having a 3-8 member carbocyclic structure or a 3-8 member heterocyclic structure, and R3 represents a hydrogen atom or a monovalent organic group. The carbazole derivative is suitable as an additive for increasing sensitivity of a chemically amplified resist. A chemically amplified radiation-sensitive resin composition, useful as a chemically amplified resist, comprising the carbazole derivative is also disclosed.