696-33-3 Usage
Description
Iodoxybenzene, also known as benzene-1-iodoxy, is an organic compound with the molecular formula C6H5IO. It is a powerful oxidizing agent known for its reactivity in organic synthesis, particularly in the oxidation of alcohols to carbonyl compounds. Its unique properties make it a versatile reagent in various chemical transformations and a candidate for pharmaceutical development and metal-catalyzed oxidation reactions.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 696-33-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,9 and 6 respectively; the second part has 2 digits, 3 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 696-33:
(5*6)+(4*9)+(3*6)+(2*3)+(1*3)=93
93 % 10 = 3
So 696-33-3 is a valid CAS Registry Number.
InChI:InChI=1/C6H5IO/c7-8-6-4-2-1-3-5-6/h1-5H
696-33-3Relevant articles and documents
Safer Synthesis of (Diacetoxyiodo)arenes Using Sodium Hypochlorite Pentahydrate
Watanabe, Ayumi,Miyamoto, Kazunori,Okada, Tomohide,Asawa, Tomotake,Uchiyama, Masanobu
, p. 14262 - 14268 (2018/11/23)
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
Taneja, Neha,Peddinti, Rama Krishna
, p. 3958 - 3963 (2016/08/11)
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
Bosset, Cyril,Coffinier, Romain,Peixoto, Philippe A.,El Assal, Mourad,Pouysegu, Laurent,Quideau, Stephane,Miqueu, Karinne,Sotiropoulos, Jean-Marc
supporting information, p. 9860 - 9864,5 (2014/10/15)
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 %.
