1829-25-0

Usage

Chemical compound

1-Methoxy-1,2-benziodoxol-3-(1H)-one is a chemical compound.

Appearance

It is a white solid.

Use as a reagent

It is commonly used as a hypervalent iodine reagent in organic synthesis.

Electrophilic iodinating agent

1-Methoxy-1,2-benziodoxol-3-(1H)-one is known for its ability to act as an electrophilic iodinating agent.

Chemical reactions

It is useful for various chemical reactions, including halogenations, oxidations, and functional group transformations.

Preparation of organic molecules

1-Methoxy-1,2-benziodoxol-3-(1H)-one is often utilized in the preparation of organic molecules.

Value in synthetic chemistry

It is considered a valuable tool in synthetic chemistry.

Stability and reactivity

The methoxy group in the compound provides stability and enhanced reactivity, making it a versatile reagent for a wide range of applications in organic synthesis.

Upstream product

• 67-56-1 methanol 
• 1829-26-1 1-acetoxy-1,2-benziodoxol-3-one 
• 124-41-4 sodium methylate 
• 87413-09-0 Dess-Martin periodane 
• 61717-82-6 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione 
• 88-67-5 2-Iodobenzoic acid 
• 131-62-4 1-hydroxy-1,2-benzodioxol-3-(1H)-one 
• 59457-26-0 1-chloro-1λ³-benzo[d][1,2]iodaoxol-3(1H)-one 
• 142260-70-6 1-(tert-butylperoxy)-1,2-benziodoxol-3(1H)-one 
• 155791-59-6 Phosphoric acid 3-oxo-3H-1λ³-benzo[d][1,2]iodoxol-1-yl ester diphenyl ester 

Downstream Products

• 887144-94-7 Togni's reagent II 
• 1825-61-2 Trimethylmethoxysilane 
• 65880-87-7 3,3-bis(methylthio)-2-methoxy-1-phenylprop-2-en-1-one 
• 131-62-4 1-hydroxy-1,2-benzodioxol-3-(1H)-one 
• 947-84-2 2-Biphenylcarboxylic acid 

Relevant academic research and scientific papers

CHEMISTRY OF AN ACYLOXYIODINANE, THE INTERMEDIATE IN IODOSOBENZOATE CATALYZED CLEAVAGE OF ACTIVE ESTERS

The 1-acetoxy-1,2-benziodoxol-3(1H)-one intermediate in the o-iodosobenzoate cleavage of p-nitrophenyl acetate can be directly observed in dimethyl sulfoxide.

Synthesis of polycyclic aminal heterocycles via decarboxylative cyclisation of dipeptide derivatives

An oxidative-decarboxylative intramolecular cyclisation of dipeptide derivatives is reported. This transformation is promoted by phenyl iodine(iii) diacetate (PIDA) in combination with BF3·OEt2. The reaction gives access to a variety of valuable polycyclic N-heterocyclic scaffolds containing 5-, 6-, or 7-membered rings.

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

Visible Light-Induced [3+2] Cyclization Reactions of Hydrazones with Hypervalent Iodine Diazo Reagents for the Synthesis of 1-Amino-1,2,3-Triazoles

In this study, visible-light-induced [3+2] cyclization reactions of hydrazones with hypervalent iodine diazo reagents as diazomethyl radical precursors are reported. Mild reaction conditions, a broad substrate scope, and excellent functional group compatibility were observed. Furthermore, the synthetic utility was demonstrated by gram-scale synthesis and elaboration to several value-added products. This protocol broadens the scope of diazo chemistry, and is applicable to the late-stage functionalization of natural products. (Figure presented.).

Practical synthesis of 2-iodosobenzoic acid (IBA) without contamination by hazardous 2-iodoxybenzoic acid (IBX) under mild conditions

We report a convenient and practical method for the preparation of nonexplosive cyclic hypervalent iodine(III) oxidants as efficient organocatalysts and reagents for various reactions using Oxone in aqueous solution under mild conditions at room temperature. The thus obtained 2-iodosobenzoic acids (IBAs) could be used as precursors of other cyclic organoiodine(III) derivatives by the solvolytic derivatization of the hydroxy group under mild conditions of 80 °C or lower temperature. These sequential procedures are highly reliable to selectively afford cyclic hypervalent iodine compounds in excellent yields without contamination by hazardous pentavalent iodine(III) compound.

Synthesis of Diverse Aryliodine(III) Reagents by Anodic Oxidation?

An anodic oxidation enabled synthesis of hypervalent iodine(III) reagents from aryl iodides is demonstrated. Under mild electrochemical conditions, a range of aryliodine(III) reagents including iodosylarenes, (difunctionaliodo)arenes, benziodoxoles and diaryliodonium salts can be efficiently synthesized and derivatized in good to excellent yields with high selectivity. As only electrons serve as the oxidation reagents, this method offers a more straightforward and sustainable manner avoiding the use of expensive or hazardous chemical oxidants.

Copper-promoted direct C-H alkoxylation of: S, S -functionalized internal olefins with alcohols

Copper-promoted direct C-H alkoxylation of S,S-functionalized internal olefins, that is, α-oxo ketene dithioacetals, was efficiently achieved with alcohols as the alkoxylating agents, (diacetoxyiodo)benzene (PhI(OAc)2) as the oxidant, and benzoquinone (BQ) as the co-oxidant. The alkoxylated olefins were thus constructed and applied for the synthesis of alkoxylated N-heterocycles. The polarization of the olefinic carbon-carbon double bond by the electron-donating dialkylthio and electron-withdrawing α-oxo functionalities plays a crucial role in making such C-H alkoxylation reactions to occur under mild conditions. Mechanistic studies implicate a single-electron-transfer (SET) reaction pathway involved in the overall catalytic cycle.

Pd(II) catalyzed ortho C-H iodination of phenylcarbamates at room temperature using cyclic hypervalent iodine reagents

A novel approach to access ortho iodinated phenols using cyclic hypervalent iodine reagents through palladium(II) catalyzed C-H activation has been developed through weak coordination. The reaction showed excellent regioselectivity, reactivity and good functional group tolerance. A unique mechanism was proposed.

Unactivated C(sp3)-H hydroxylation through palladium catalysis with H2O as the oxygen source

A novel palladium catalyzed hydroxylation of unactivated aliphatic C(sp3)-H bonds was successfully developed. Different from conventional methods, water serves as the hydroxyl group source in the reaction. This new reaction demonstrates good reactivity and broad functional group tolerance. The C-H hydroxylated products can be readily transformed into various highly valuable chemicals via known transformations. Based on experimental and theoretical studies, a mechanism involving the Pd(ii)/(iv) pathway is proposed for this hydroxylation reaction.

Dual Hypervalent Iodine(III) Reagents and Photoredox Catalysis Enable Decarboxylative Ynonylation under Mild Conditions

A combination of hypervalent iodine(III) reagents (HIR) and photoredox catalysis with visible light has enabled chemoselective decarboxylative ynonylation to construct ynones, ynamides, and ynoates. This ynonylation occurs effectively under mild reaction conditions at room temperature and on substrates with various sensitive and reactive functional groups. The reaction represents the first HIR/photoredox dual catalysis to form acyl radicals from α-ketoacids, followed by an unprecedented acyl radical addition to HIR-bound alkynes. Its efficient construction of an mGlu5 receptor inhibitor under neutral aqueous conditions suggests future visible-light-induced biological applications.