696-33-3

Basic information

• Product Name: Iodoxybenzene
• Synonyms: Dioxophenyliodine(V);Iodylbenzene;Phenyldioxyiodine(V);Benzene, iodyl-;Nsc 60684
• CAS NO: 696-33-3
• Molecular Formula: C₆H₅IO₂
• Molecular Weight: 236.0
• Mol File: 696-33-3.mol
• Article Data: 23

Chemical Properties

• Melting Point: 230°C
• Boiling Point: 198.4°C at 760 mmHg
• Flash Point: 73.8°C
• Appearance: /
• Density: 1.8665 (estimate)
• Vapor Pressure: 0.508mmHg at 25°C
• Refractive Index: 1.631
• CAS DataBase Reference: Iodoxybenzene(CAS DataBase Reference)
• NIST Chemistry Reference: Iodoxybenzene(696-33-3)
• EPA Substance Registry System: Iodoxybenzene(696-33-3)

Safety Data

• Statements: R1
• Safety Statements: 35
• Hazardous Substances Data: 696-33-3(Hazardous Substances Data)

Usage

General Description

Iodoxybenzene, also known as benzene-1-iodoxy, is an organic compound with the molecular formula C6H5IO. It is a powerful oxidizing agent and is used as a reagent in organic synthesis. Iodoxybenzene is particularly useful in the oxidation of alcohols to carbonyl compounds, and it also participates in other types of oxidation reactions such as the conversion of sulfides to sulfoxides and the cleavage of vicinal diols to carbonyl compounds. Additionally, iodoxybenzene has been studied for its potential applications in the development of new pharmaceuticals and as a reagent in metal-catalyzed oxidation reactions. However, it is important to note that iodoxybenzene is a highly toxic and potentially explosive chemical, requiring careful handling and storage.

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 
• 64846-42-0 C₂₂H₅F₂₈IO₈ 
• 84-11-7 9,10-phenanthrenequinone 
• 84-65-1 9,10-phenanthrenequinone 
• 17105-71-4 N-methyl-N-benzylformamide 
• 100-52-7 benzaldehyde 
• 65-85-0 benzoic acid 
• 536-80-1 iodosylbenzene 
• 50700-49-7 N-acetyl-p-benzoquinoneimine 
• 780-25-6 N-benzylidene benzylamine 
• 81-84-5 1,8-Naphthalic anhydride 
• 66959-13-5 Bis-(perfluorbutyroxy)-iodylbenzol 

Relevant articles and documents

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.

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

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 %.