536-80-1

Basic information

• Product Name: IODOSOBENZENE
• Synonyms: iodoso-benzen;iodosyl-benzen;IODOSOBENZENE;4-05-00-00692 (Beilstein Handbook Reference);[Oxoiodo(III)]benzene;Phenyliodine(III) oxide;Phenyloxoiodine(III);Benzene, iodosyl-
• CAS NO: 536-80-1
• Molecular Formula: C₆H₅IO
• Molecular Weight: 220.01
• EINECS: 208-648-8
• Product Categories: Benzene derivatives;Hypervalent Iodine Compounds;Oxidation;Synthetic Organic Chemistry
• Mol File: 536-80-1.mol
• Article Data: 60

Chemical Properties

• Melting Point: 210°C (rough estimate)
• Appearance: /
• Density: 1.8665 (estimate)
• Storage Temp.: Freezer
• Water Solubility: Slightly soluble in water
• Merck: 14,5044
• CAS DataBase Reference: IODOSOBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: IODOSOBENZENE(536-80-1)
• EPA Substance Registry System: IODOSOBENZENE(536-80-1)

Safety Data

• Safety Statements: 17-36/37/39
• RIDADR: 1479
• RTECS: DA3500000
• HazardClass: 4.1
• PackingGroup: II
• Hazardous Substances Data: 536-80-1(Hazardous Substances Data)

Usage

Chemical Properties

Iodosobenzene is an amorphous yellow substance; it explodes at 210℃, decomposing with the evolution of iodine vapour, and dissolves in hot water and alcohol. If acids do not oxidise C6H5IO, they give saline compounds in which iodosobenzene appears as a basic oxide of a diatomic metal, C6H5I. Thus, for instance, when an acetic acid solution of iodosobenzene is treated with a solution of nitric acid, it gives large monoclinic crystals of a nitric acid salt having the composition C6H5(NO3)2 [like Ca(NO3)2). Iodosobenzene displaces iodine from potassium iodide (in a solution acidulated with acetic or hydrochloric acid)-ie, it acts with its oxygen like HClO. The action of peroxide of hydrogen, chromic acid, and other similar oxidising agents gives C6H5IO2, which is a neutral substance-i.e, is incapable of giving salts with acids.Iodosobenzene is one of the very first oxidants and remains in use because it has excellent oxygen-transfer behavior and mechanistic cleanliness (Hill & Schardt, 1980; Rezaeifard et al., 2007; Po?towicz et al., 2006).The Principles of Chemistry Volume 1

Uses

Different sources of media describe the Uses of 536-80-1 differently. You can refer to the following data:
1. Oxygen transfer reagent for stiochiometric or catalytic cross-functionalization of alkenes, alcohols, sulfides, and organometallo Compounds.Iodosobenzene is used as an oxidizing and acetoxylating agent in organic synthesis. It is actively involved in the preparation of (Z)-3,7-dimethyl-2,6-octadien-1-al(neral) from (Z)-3,7-dimethyl-2,6-octadien-1-ol (nerol) in presence of 2,2,6,6-tetramethylpiperidin-1-oxyl (TEMPO). It is a useful reagent for the synthesis of a wide variety of heterocyclic compounds. It is also used in the Pd-catalyzed 2-arylation of indoles.
2. lodosobenzene is a relatively new, selective oxidizing agent which is particularly useful for the preparation of sulfoxides from unsaturated or otherwise sensitive sulfides. The preparation of diallyl, di-2-hydroxyethyl and phenyl 2-chloroethyl sulfoxides illustrates its use.Iodosobenzene diacetate behaves similarly and oxidizes diphenyl and 4-nitro-phenyl 4'-carboxyphenyl sulfide exclusively to the sulfoxides. This reagent failed, however, to oxidize bis(2-nitro-4-trifuoromethylphenyl) sulfide and in the case of bis(2-aminophenyl) sulfide it gave complex products. Iodosobenzene diacetate caused diacetoxylation of the heterocycle of 2,5-diphenyl-1 ,4-dithiadiene rather than oxidation of the sulfide function, and with 2,5-diphenylI-1 ,4-dithiadiene-1-oxide unexpected results were obtained, as discussed in section C-4.Organic Sulfur Compounds

Synthesis

Iodosobenzene has been prepared by the action of sodium or potassium hydroxide solution on iodobenzene dichloride and by addition of water to the dichloride.Iodosobenzene is prepared from iodobenzene.It is prepared by first oxidizing iodobenzene by peracetic acid. Hydrolysis of resulting diacetate affords "PhIO":C6H5I + CH3CO3H + CH3CO2H → C6H5I(O2CCH3)2 + H2OC6H5I(O2CCH3)2 + H2O → C6H5IO + 2CH3CO2Hhttp://orgsyn.org

InChI:InChI=1/C6H5IO/c8-7-6-4-2-1-3-5-6/h1-5H

Upstream product

• 591-50-4 iodobenzene 
• 10028-15-6 ozone 
• 7601-90-3 perchloric acid 
• 64-19-7 acetic acid 
• 7664-93-9 sulfuric acid 
• 16975-78-3 bis(acetoxy)iodylbenzene 
• 1613-37-2 Quinoline N-oxide 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 26735-53-5 iodobenzene difluoride 
• 429-41-4 tetrabutyl ammonium fluoride 
• 932-72-9 (Dichloroiodo)benzene 
• 7732-18-5 water 
• 696-33-3 iodoxybenzene 
• 123-30-8 4-amino-phenol 

Downstream Products

• 85083-59-6 iodobenzene dimethoxide 
• 91146-10-0 cis-1,2-cyclohexanediyl 1,2-bis(trifluoromethanesulfonate) 
• 115298-63-0 phenyl(4-methoxyphenyl)iodonium triflate 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 114820-32-5 4-Nitro-benzenesulfonatephenyl-prop-1-ynyl-iodonium; 
• 94957-41-2 phenyl(propenyl)iodonium tosylate 
• 1932-53-2 1-phenyl-1λ³-[1,2,7]iodadioxepane-3,6-dione 
• 100-52-7 benzaldehyde 
• 6597-18-8 (dibenzoyloxyiodo)benzene 
• 2665-60-3 (p-methylphenyl)phenyliodonium bromide 
• 591-50-4 iodobenzene 
• 92-52-4 biphenyl 
• 10182-84-0 diphenyliodonium 
• 55145-91-0 4-acetylaminodiphenyliodonium bromide 

Relevant articles and documents

Chiral-at-Ruthenium Catalyst with Sterically Demanding Furo[3,2-b]pyridine Ligands

A sterically demanding derivative of a previously introduced chiral-at-metal ruthenium(II) catalyst scaffold is introduced. It is composed of two bidentate furo[3,2-b]pyridyl functionalized N-heterocyclic carbene ligands. Their cis-coordination generates helical chirality and a stereogenic ruthenium center. Two additional labile acetonitriles compose the catalytic site which is highly shielded by two 2-(tert-butyl)furo[3,2-b]pyridine moieties. The synthesis of the non-racemic ruthenium catalyst and its catalytic properties for the enantioselective alkynylation of 2,2,2-trifluoroacetophenone and pentafluorobenzaldehyde are reported and compared with sterically less demanding derivatives.

Modifying the Product Distribution of a Reaction within the Controlled Microenvironment of a Colloidosome

A water-soluble colloidosome composed of PGMA-PS latex was used as a microcapsule to host a catalyzed oxidation reaction within its dodecane core. When compared to a control reaction a significant colloidosome effect was observed. Specifically, a 233% increase in the relative yield of all products was observed for the colloidosome reaction. Furthermore, when the product distributions were calculated it was evident that a switch in selectivity had taken place. These studies showed there is a significant reduction in the relative yield of the epoxide product compared to the remaining oxidation products. Additional control experiments confirmed that rate enhancements were not simply a result of concentration and that reactions were not occurring in the outer latex phase. As a consequence of these control experiments, we suggest that the colloidosome enhancement and shift in product distribution, comes about from differences in electronic environment at or close to the interface between the internal oil phase and the outer colloidal particles. This environment is able to stabilize any specific intermediates and or transition states leading to enhanced reactions for these products and higher relative yields.

CO2-activated NaClO-5H2O enabled smooth oxygen transfer to iodoarene: A highly practical synthesis of iodosylarene

A safe, rapid, and environmentally friendly synthesis of iodosylarene (ArIO) has been developed using NaClO under a carbon dioxide (CO2) atmosphere. Exposure of iodoarene to NaClO-5H2O in acetonitrile under CO2 (1 atm) resulted in the clean formation of ArIO within 10 minutes in high yield. The absence of a base in this method enables the direct use of in-situ-generated iodosylarene not only for a variety of oxidative transformations (synthesis of sulfilimine, pentavalent bismuth, benzyne adduct, etc.), but also for the synthesis of iodonium ylide and imino-λ3-iodane in one pot.

N?N Bond Formation Using an Iodonitrene as an Umpolung of Ammonia: Straightforward and Chemoselective Synthesis of Hydrazinium Salts

The formation of hydrazinium salts by N?N bond formation has typically involved the use of hazardous and difficult to handle reagents. Here, mild and operationally simple conditions for the synthesis of hydrazinium salts are reported. Electrophilic nitrogen transfer to the nitrogen atom of tertiary amines is achieved using iodosylbenzene as oxidant and ammonium carbamate as the N-source. The resulting process is highly chemoselective and tolerant to other functional groups. A wide scope is reported, including examples with bioactive molecules. Insights on the structure of hydrazinium salts were provided by X-ray analysis. (Figure presented.).