1580548-81-7

Basic information

• Product Name: 1-Acetoxy-5-broMo-1,2-benziodoxol-3(1H)-one
• Synonyms: 1-Acetoxy-5-broMo-1,2-benziodoxol-3(1H)-one;1-Acetoxy-5-bromo-1,2-benziodoxol-3(1H)-one
• CAS NO: 1580548-81-7
• Molecular Formula: C9H6BrIO4
• Molecular Weight: 384.95001
• Mol File: 1580548-81-7.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-Acetoxy-5-broMo-1,2-benziodoxol-3(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Acetoxy-5-broMo-1,2-benziodoxol-3(1H)-one(1580548-81-7)
• EPA Substance Registry System: 1-Acetoxy-5-broMo-1,2-benziodoxol-3(1H)-one(1580548-81-7)

Safety Data

• Hazardous Substances Data: 1580548-81-7(Hazardous Substances Data)

Usage

General Description

1-acetoxy-5-bromo-1,2-benziodoxol-3(1H)-one, also known as ABX, is a synthetic compound with a molecular formula of C8H6BrIO4. It is a hypervalent iodine compound that is commonly used as a reagent in organic synthesis. ABX is known for its versatile reactions in organic chemistry, particularly in the formation of carbon-carbon and carbon-heteroatom bonds. It can be used in various reactions such as oxidative rearrangements, cyclization, and functional group transformations. ABX is a powerful oxidizing agent and is known for its high reactivity. It is often used as a substitute for hazardous and toxic reagents, making it a valuable tool in the field of organic synthesis.

Upstream product

• 21740-00-1 5-bromo-2-iodo-benzoic acid 
• 64-19-7 acetic acid 
• 108-24-7 acetic anhydride 

Relevant articles and documents

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.

Oxidation of Alcohols to Aldehydes or Ketones with 1-Acetoxy-1,2-benziodoxole-3(1H)-one Derivatives

Various benzylic and aliphatic alcohols were smoothly oxidized to the corresponding aromatic aldehydes and ketones as well as aliphatic ketones by treatment with 1-acetoxy-5-nitro-1,2-benziodoxole-3(1H)-one (ANBX), 1-acetoxy-5-bromo-1,2-benziodoxole-3(1H)-one (ABBX), 1-acetoxy-5-chloro-1,2-benziodoxole-3(1H)-one (ACBX), and 1-acetoxy-5-fluoro-1,2-benziodoxole-3(1H)-one (AFBX). These new trivalent iodine compounds were prepared from 5-substituted 2-iodobenzoic acids and meta-chloroperoxybenzoic acid (m-CPBA). ANBX and ABBX were the most effective reagents for this oxidation of alcohols, and this present reaction is very attractive because of the ease of product isolation and the reusability of the reagents.