696-33-3

Usage

Uses

Used in Organic Synthesis:
Iodoxybenzene is used as an oxidizing reagent for the conversion of alcohols to carbonyl compounds, a critical transformation in the synthesis of complex organic molecules. Its ability to selectively oxidize primary and secondary alcohols without over-oxidation to carboxylic acids makes it a valuable tool in organic chemistry.
Used in Pharmaceutical Development:
Iodoxybenzene is studied for its potential applications in the development of new pharmaceuticals. Its strong oxidizing properties can be harnessed to create novel drug candidates with unique mechanisms of action, potentially leading to the discovery of new treatments for various diseases.
Used in Metal-Catalyzed Oxidation Reactions:
Iodoxybenzene serves as a reagent in metal-catalyzed oxidation reactions, where it can enhance the efficiency and selectivity of oxidation processes. This application is particularly relevant in the synthesis of fine chemicals and pharmaceutical intermediates, where precise control over oxidation states is crucial.
Used in the Conversion of Sulfides to Sulfoxides:
Iodoxybenzene is utilized in the selective oxidation of sulfides to sulfoxides, a transformation that is important in the synthesis of chiral compounds and the preparation of certain pharmaceuticals. Its ability to perform this oxidation without affecting other functional groups in a molecule highlights its synthetic utility.
Used in the Cleavage of Vicinal Diols to Carbonyl Compounds:
In the context of carbohydrate chemistry and the synthesis of complex polyol derivatives, iodoxybenzene is employed for the cleavage of vicinal diols to carbonyl compounds. This reaction is useful for the construction of aldehydes and ketones from diols, expanding the synthetic potential of these substrates.

InChI:InChI=1/C6H5IO/c7-8-6-4-2-1-3-5-6/h1-5H

Upstream product

• 93-59-4 Perbenzoic acid 
• 591-50-4 iodobenzene 
• 67-66-3 chloroform 
• 60-29-7 diethyl ether 
• 110-22-5 diacetyl peroxide 
• 536-80-1 iodosylbenzene 
• 932-72-9 (Dichloroiodo)benzene 
• 87301-33-5 Bisiodobenzene 
• 1015765-81-7 iodosylbenzene 
• 75-07-0 acetaldehyde 
• 64-19-7 acetic acid 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 22121-26-2 phenyliodine(V) tetrafluoride 
• 64846-35-1 Tetrakisiodobenzene 

Downstream Products

• 591-50-4 iodobenzene 
• 16825-78-8 1-iodoxy-3-nitrobenzene 
• 5584-41-8 4,4'-bis-phenyliodonio-biphenyl; diiodide 
• 16975-78-3 bis(acetoxy)iodylbenzene 
• 64846-35-1 Tetrakisiodobenzene 
• 64846-42-0 C₂₂H₅F₂₈IO₈ 
• 17105-71-4 N-methyl-N-benzylformamide 
• 780-25-6 N-benzylidene benzylamine 
• 100-52-7 benzaldehyde 
• 1785-51-9 pyrene-1,6-dione 
• 2304-85-0 pyrene-1,8-dione 
• 6217-22-7 pyrene-4,5-dione 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 119-61-9 benzophenone 

Relevant academic research and scientific papers

Safer Synthesis of (Diacetoxyiodo)arenes Using Sodium Hypochlorite Pentahydrate

A practical method for the preparation of (diacetoxyiodo)arene ArI(OAc)2 is described. The use of commercially available sodium hypochlorite pentahydrate (NaClO·5H2O) enabled safe, rapid, and inexpensive oxidation of iodoarenes with electron-withdrawing and -donating substituents. The method allows tandem divergent access to synthetically useful organo-λ3-iodanes such as hydroxyl(tosyloxy)iodobenzene, iodosylbenzene, iodonium ylide, etc.

Mild and efficient synthesis of iodylarenes using Oxone as oxidant

Mild and efficient method for the preparation of iodylarenes by oxidation of iodoarenes with Oxone in aqueous acetonitrile at room temperature is described. This new procedure allows the preparation of various iodylarenes with electron-donating or electron-withdrawing substituents in the aromatic ring including the previously unknown 1,2-diiodylbenzene.

Iodobenzene and m-chloroperbenzoic acid mediated oxidative dearomatization of phenols

Oxidative dearomatization of 2- and 4-substituted phenols to their corresponding benzoquinone monoketals by catalytic amount of iodobenzene, and m-CPBA as a co-oxidant has been achieved via in situ generation of PhIO2, a hypervalent iodine(V) s

Oxidations of alkenes with hypervalent iodine reagents: An alternative ozonolysis of phenyl substituted alkenes and allylic oxidation of unsubstituted cyclic alkenes

Unsaturated CC double bonds with a phenyl substituent can be cleaved with iodylbenzene and iodosylbenzene to give carbonyl compounds. It is believed that the reactions occur via a radical pathway. The allylic oxidation of cyclic alkenes lacking a phenyl substituent was achieved in acetonitrile/water mixture (3:1) also using iodylbenzene and iodosylbenzene.

Asymmetric hydroxylative phenol dearomatization promoted by chiral binaphthylic and biphenylic iodanes

The long-standing quest for chiral hypervalent organoiodine compounds (i.e., iodanes) as metal-free reagents for asymmetric synthesis continues. Although remarkable progress has recently been made in organoiodine-catalyzed reactions using a terminal oxidant in stoichiometric amounts, there is still a significant need for "flaskable" chiral iodane reagents. Herein, we describe the synthesis of new iodobinaphthyls and iodobiphenyls, their successful and selective DMDO-mediated oxidation into either λ3- or λ5-iodanes, and the evaluation of their capacity to promote asymmetric hydroxylative phenol dearomatization (HPD) reactions. Most notably, a C2-symmetrical biphenylic λ5-iodane promoted the HPD-induced conversion of the monoterpene thymol into the corresponding ortho-quinol-based [4+2] cyclodimer (i.e., bis(thymol)) with enantiomeric excesses of up to 94 %.

A direct method for oxidizing quinoxaline, tetraazaphenanthrene, and hexaazatriphenylene moieties using hypervalent λ3-iodinane compounds

An efficient oxidation reaction of various electron-poor quinoxaline-core-containing compounds, such as quinoxalines, 1,4,5,8-tetraazaphenanthrenes, and 1,4,5,8,9,12-hexaazatriphenylene, using [bis(trifluoroacetoxy)iodo]benzene is reported. These compounds are converted into the corresponding quinoxalinediones in good to high yields at room temperature using an acetonitrile/water solvent mixture. This unprecedented reaction should enable the synthesis of a wide variety of compounds useful in several fields of chemistry.

Transition metal-mediated oxidations utilizing monomeric iodosyl- and iodylarene species

Several transition metal-mediated oxidations using hypervalent iodine species are reported. A convenient procedure for preparation of iodylarenes via RuCl3-catalyzed oxidation of iodoarenes has been developed. This procedure allows the generation of highly reactive monomeric iodine(V) species, which are excellent oxidants toward alcohols and hydrocarbons in situ. A broad range of substrates can be oxidized to carbonyl compounds by a tandem catalytic system based on the Ru(III)-catalyzed reoxidation of ArIO to ArIO2 using Oxone as oxidant. It was shown that electrophilic iodine(III) species, originating from oligomeric iodosylbenzene sulfate (PhIO)3SO3, are efficient oxygenating agents in catalytic oxidation of aromatic hydrocarbons in the presence of metalloporphyrin complexes.

NUCLEOPHILIC FLUORINATION OF AROMATIC COMPOUNDS

Iodylbenzene derivatives substituted with electron donating as well as electron withdrawing groups on the aromatic ring are used as precursors in aromatic nucleophilic substitution reactions. The iodyl group (IO2) is regiospecifically substituted by nucleophilic fluoride to provide the corresponding fluoroaryl derivatives. No-carrier-added [F-18] fluoride ion derived from anhydrous [F- 18]KF/Kryptofix, [F-18]CsF or a quaternary ammonium fluoride (e.g., Me4NF, Et4NF, n-Bu4NF, (PhCH2)4NF) exclusively substitutes the iodyl moiety in these derivatives and provides high specific activity F- 18 labeled fluoroaryl analogs. Iodyl derivatives of a benzothiazole analog and 6-iodyl-L-dopa derivatives have been synthesized as precursors and have been used in the preparation of no-carrier-added [F-18]fluorobenzothiazole as well as 6-[F-18]fluoro-L-dopa.

Iodine(V)/ruthenium(III)-cocatalyzed oxidations: A highly efficient tandem catalytic system for the oxidation of alcohols and hydrocarbons with oxone

An extremely mild and efficient tandem catalytic system for the oxidation of alcohols and hydrocarbons based on Ru(III)-catalyzed reoxidation of ArIO to ArIO2 was reported, by using Oxone as a stoichiometric oxidant. Oxone was added to a mixture of propylbenzene, PhI, and RuCl3 in acetonitrile and water in five portions over 22 h under stirring at room temperature. The reaction mixture was stirred for an additional 4 h and was monitored by TLC by the disappearance of propylbenzene. Then ethyl acetate and water were added and the mixture was stirred for 5 mm. The organic solution was separated and the aqueous phase was extracted with ethyl acetate. The organic phases were combined, washed with NaCl, and dried over Na2SO 4. The oxidation of the other hydrocarbons was performed by using a similar procedure. The use of smaller amounts of Oxone led to incomplete conversion owing to its noticeable decomposition with loss of oxygen gas under reaction conditions.

Highly efficient RuCl3-catalyzed disproportionation of (diacetoxyiodo)benzene to iodylbenzene and iodobenzene; leading to the efficient oxidation of alcohols to carbonyl compounds

(Diacetoxyiodo)benzene (DIB) selectively oxidizes primary and secondary alcohols to the respective carbonyl compounds in the presence of RuCl3 (0.8-1.0 mol %) at room temperature in aqueous acetonitrile. This reaction proceeds via an initial instantaneous Ru-catalyzed disproportionation of DIB to iodobenzene and iodylbenzene with the latter acting as the actual stoichiometric oxidant toward alcohols.