1829-26-1

Basic information

• Product Name: 1,2-Benziodoxol-3(1H)-one, 1-(acetyloxy)-
• CAS NO: 1829-26-1
• Molecular Formula: C9H7IO4
• Molecular Weight: 306.057
• Mol File: 1829-26-1.mol
• Article Data: 60

Chemical Properties

• CAS DataBase Reference: 1,2-Benziodoxol-3(1H)-one, 1-(acetyloxy)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Benziodoxol-3(1H)-one, 1-(acetyloxy)-(1829-26-1)
• EPA Substance Registry System: 1,2-Benziodoxol-3(1H)-one, 1-(acetyloxy)-(1829-26-1)

Safety Data

• Hazardous Substances Data: 1829-26-1(Hazardous Substances Data)

Usage

General Description

1,2-Benziodoxol-3(1H)-one, 1-(acetyloxy)- is a synthetic chemical compound with the molecular formula C8H5IO4. It is a powerful and versatile reagent with applications in organic synthesis, particularly in the preparation of complex organic molecules. The compound is used as a hypervalent iodine reagent, capable of oxidizing a variety of substrates, and has been utilized in the development of new synthetic methodologies and in the total synthesis of natural products. Additionally, it has been investigated for its potential as an antibacterial and antifungal agent. Despite its potential applications, the compound should be handled with care due to its highly reactive and potentially hazardous nature.

Upstream product

• 79-21-0 peracetic acid 
• 88-67-5 2-Iodobenzoic acid 
• 59457-26-0 1-chloro-1λ³-benzo[d][1,2]iodaoxol-3(1H)-one 
• 64-19-7 acetic acid 
• 618-51-9 3-Iodobenzoic acid 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 131-62-4 1-hydroxy-1,2-benzodioxol-3-(1H)-one 
• 127-08-2 potassium acetate 
• 108-24-7 acetic anhydride 
• 87413-09-0 Dess-Martin periodane 
• 830-03-5 4-nitrophenol acetate 
• 678-39-7 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-1-decanol 
• 84280-67-1 1-oxido-1,2-benziodoxol-3(1H)-one 
• 304-91-6 o-iodosobenzoic acid 

Downstream Products

• 1829-25-0 1-methoxy-1λ³-benzo[d][1,2]iodaoxol-3(1H)-one 
• 1829-24-9 1-ethoxy-1λ³-benzo[d][1,2]iodaoxol-3(1H)-one 
• 887144-94-7 Togni's reagent II 
• 88-67-5 2-Iodobenzoic acid 
• 94298-51-8 N-methyl-N,3-diphenylprop-2-ynamide 
• 943338-77-0 1-(3,4-dihydroisoquinolin-2(1H)-yl)-3-(phenyl)prop-2-yn-1-one 
• 1557159-81-5 1-(2-phenylethynyl)-1,2-benziodoxol-3(1H)-one 

Relevant articles and documents

N-Cyanation of Primary and Secondary Amines with Cyanobenzio-doxolone (CBX) Reagent

An efficient electrophilic N-cyanation of amines with a stable and less-toxic cyanobenziodoxole reagent towards the synthesis of cyanamides is disclosed. This synthetically practicable strategy allows the construction of a wide variety of cyanamides under very mild and simple conditions with a broad functional group compatibility, and showcases a huge potential in late-stage modification of complex molecules.

Site Selective Chlorination of C(sp3)?H Bonds Suitable for Late-Stage Functionalization

C(sp3)?Cl bonds are present in numerous biologically active small molecules, and an ideal route for their preparation is by the chlorination of a C(sp3)?H bond. However, most current methods for the chlorination of C(sp3)?H bonds are insufficiently site selective and tolerant of functional groups to be applicable to the late-stage functionalization of complex molecules. We report a method for the highly selective chlorination of tertiary and benzylic C(sp3)?H bonds to produce the corresponding chlorides, generally in high yields. The reaction occurs with a mixture of an azidoiodinane, which generates a selective H-atom abstractor under mild conditions, and a readily-accessible and inexpensive copper(II) chloride complex, which efficiently transfers a chlorine atom. The reaction's exceptional functional group tolerance is demonstrated by the chlorination of >30 diversely functionalized substrates and the late-stage chlorination of a dozen derivatives of natural products and active pharmaceutical ingredients.

Tosyloxybenziodoxolone: A Platform for Performing the Umpolung of Alkynes in One-Pot Transformations

Ethynylbenziodoxolones (EBXs) are commonly encountered reagents for the electrophilic alkynylation of nucleophiles. Herein, we report a one-pot, two-step process for EBX generation and their direct application in substrate functionalization. Our approach enables us to bypass the originally mandatory isolation and purification of the reagents, resulting in a more efficient synthesis. We could apply this process to seven different transformations involving both two- and one-electron nucleophiles to obtain a large variety of alkynylated products.