131-62-4

Basic information

• Product Name: 1-Hydroxy-2-oxa-1-ioda(III)indan-3-one
• Synonyms: 1-Hydroxy-1,2-benziodoxole-3-one;1-Hydroxy-1,3-dihydro-1,2-benziodoxole-3-one;1-Hydroxy-1-ioda(III)-2-oxaindan-3-one;1-Hydroxy-2-oxa-1-ioda(III)indan-3-one;1-Hydroxy-3-oxo-1,3-dihydro-1,2-benzoiodoxole;1-Hydroxy-1H-1|-benzo[d][1,2]iodoxol-3-one;1,2-Benziodoxol-3(1H)-one,1-hydroxy-;1-hydroxy-3H-1λ3,2-benziodaoxol-3-one
• CAS NO: 131-62-4
• Molecular Formula: C₇H₅IO₃
• Molecular Weight: 264.02
• Mol File: 131-62-4.mol
• Article Data: 119

Chemical Properties

• Melting Point: 260 °C (decomp)(Solv: water (7732-18-5))
• Appearance: /
• PKA: 8.12±0.20(Predicted)
• CAS DataBase Reference: 1-Hydroxy-2-oxa-1-ioda(III)indan-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Hydroxy-2-oxa-1-ioda(III)indan-3-one(131-62-4)
• EPA Substance Registry System: 1-Hydroxy-2-oxa-1-ioda(III)indan-3-one(131-62-4)

Safety Data

• Hazardous Substances Data: 131-62-4(Hazardous Substances Data)

Usage

Uses

1-?Hydroxy-?1,?2-?benziodoxol-?3(1H)?-?one (IBA) is an efficient terminal oxidant for gold-?catalyzed, three-?component oxyarylation reactions. It also acted as a catalyst in synthesis of ynones via a hypervalent iodine-catalyzed reaction.

Definition

ChEBI: A benziodoxole compound having a hydroxy substituent at the 1-position and an oxo substituent at the 3-position.

InChI:InChI=1/C7H5IO3/c9-7-5-3-1-2-4-6(5)8(10)11-7/h1-4,10H

Upstream product

• 615-37-2 ortho-methylphenyl iodide 
• 15753-50-1 cis-1,2-cyclohexanedimethanol 
• 1829-25-0 1-methoxy-1λ³-benzo[d][1,2]iodaoxol-3(1H)-one 
• 610-97-9 o-iodo-methyl-benzoic acid 
• 591-50-4 iodobenzene 
• 64-19-7 acetic acid 
• 160732-56-9 1-azido-1λ³-benzo[d][1,2]iodaoxol-3(1H)-one 
• 88-67-5 2-Iodobenzoic acid 
• 7732-18-5 water 
• 61717-82-6 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione 
• 59457-26-0 1-chloro-1λ³-benzo[d][1,2]iodaoxol-3(1H)-one 
• 1493-13-6 trifluorormethanesulfonic acid 
• 142260-70-6 1-(tert-butylperoxy)-1,2-benziodoxol-3(1H)-one 
• 185566-86-3 1-(1-Isopropyl-2-methyl-propoxy)-1-oxo-1H-1λ⁵-benzo[d][1,2]iodoxol-3-one 

Downstream Products

• 1829-26-1 1-acetoxy-1,2-benziodoxol-3-one 
• 108981-92-6 2-(naphthalene-1-yl)benzoic acid 
• 18110-71-9 4'-methoxybiphenyl-2-carboxylic acid 
• 7148-03-0 o-tolylbenzoic acid 
• 7111-77-5 2'-methyl[1,1'-biphenyl]-carboxylic acid 
• 947-84-2 2-Biphenylcarboxylic acid 
• 88-67-5 2-Iodobenzoic acid 
• 1557159-81-5 1-(2-phenylethynyl)-1,2-benziodoxol-3(1H)-one 
• 172876-96-9 3-oxo-1λ³-benzo[d][1,2]iodaoxole-1(3H)-carbonitrile 
• 164268-31-9 phenylethynyl(o-carboxyphenyl)iodonium triflate 
• 164268-27-3 1-hexynyl-(o-carboxyphenyl)iodonium triflate 
• 160732-56-9 1-azido-1λ³-benzo[d][1,2]iodaoxol-3(1H)-one 
• 159950-96-6 1-(p-methylbenzenesulfonyloxy)-1,2-benziodoxol-3(1H)-one 

Relevant articles and documents

Photoredox Imino Functionalizations of Olefins

Shown herein is that polyfunctionalized nitrogen heterocycles can be easily prepared by a visible-light-mediated radical cascade process. This divergent strategy features the oxidative generation of iminyl radicals and subsequent cyclization/radical trapping, which allows the effective construction of highly functionalized heterocycles. The reactions proceed efficiently at room temperature, utilize an organic photocatalyst, use simple and readily available materials, and generate, in a single step, valuable building blocks that would be difficult to prepare by other methods.

Enantioselective Synthesis of Homoallylic Azides and Nitriles via Palladium-Catalyzed Decarboxylative Allylation

Azides and nitriles are important building blocks for the synthesis of nitrogen-containing bioactive compounds. The first example of enantioselective palladium-catalyzed decarboxylative allylation of α-azido and cyano β-ketoesters is reported. Indanone derivatives were obtained in 50-88% yield/77-97% ee and 46-98% yield/78-93% ee for azide and nitrile substituents, respectively. The required starting materials were synthesized in one step from ketoesters via electrophilic azidation and cyanation using benziodoxole hypervalent iodine reagents. The products could be easily converted into useful nitrogen-containing building blocks, such as triazoles, amides, or α- and β- amino ketones.

o-Iodosobenzoate: Catalyst for the Micellar Cleavage of Activated Esters and Phosphates

-

-

-

The direct electrophilic cyanation of β-keto esters and amides with cyano benziodoxole

The direct electrophilic α-cyanation of β-keto esters and amides has been developed using a hypervalent iodine benziodoxole-derived cyano reagent. The procedure is accomplished within 10 min and without the use of any catalyst in DMF, at room temperature. Thus, the highly functionalized quaternary carbon-centered nitriles were produced in high to excellent yields.

Thermal stability of N-heterocycle-stabilized iodanes-A systematic investigation

The thermal stability of pseudocyclic and cyclic N-heterocycle-stabilized (hydroxy)aryl-and mesityl(aryl)-λ3-iodanes (NHIs) through thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC) is investigated. Peak decomposition temperatures (Tpeak) were observed within a wide range between 120 and 270 °C. Decomposition enthalpies (ΔHdec) varied from-29.81 to 141.13 kJ/mol. A direct comparison between pseudocyclic and cyclic NHIs revealed high Tpeak but also higher ΔHdec values for the latter ones. NHIs bearing N-heterocycles with a high N/C-ratio such as triazoles show among the lowest Tpeak and the highest ΔHdec values. A comparison of NHIs with known (pseudo)cyclic benziodoxolones is made and we further correlated their thermal stability with reactivity in a model oxygenation.

Hypervalent Iodine(III) Reagents with Transferable Primary Amines: Structure and Reactivity on the Electrophilic α-Amination of Stabilized Enolates

A new family of hypervalent iodine reagents containing transferable primary amine groups is described. Benziodoxolone-based reagents were synthesized on the gram-scale through operationally simple reactions in up to quantitative yields. These bench-stable solids were characterized by X-ray analysis and successfully employed in the α-amination of indanone-based β-ketoesters in up to 83% yield. Mechanistic studies indicate a substitution mechanism involving an electrophilic amine.

N-Terminal Selective C?H Azidation of Proline-Containing Peptides: a Platform for Late-Stage Diversification

A methodology for the C?H azidation of N-terminal proline-containing peptides was developed employing only commercially available reagents. Peptides bearing a broad range of functionalities and containing up to 6 amino acids were selectively azidated at the carbamate-protected N-terminal residue in presence of the numerous other functional groups present on the molecules. Post-functionalizations of the obtained aminal compounds were achieved: cycloaddition reactions or C?C bond formations via a sequence of imine formation/nucleophilic addition were performed, offering an easy access to diversified peptides.

1,3-Oxyalkynylation of Aryl Cyclopropanes with Ethylnylbenziodoxolones Using Photoredox Catalysis

Alkynes and cyclopropanes are vital motifs in chemistry. Herein, a photoredox catalyzed 1,3-oxyalkynylation of aryl cyclopropanes with ethylnylbenziodoxolones (EBXs) in an atom-economic fashion is described. This cascade comprises single-electron oxidatio