69352-04-1

Basic information

• Product Name: 1-Chloro-1,3-dihydro-3,3-diMethyl-1,2-benziodoxole
• Synonyms: 1-Chloro-1,3-dihydro-3,3-diMethyl-1,2-benziodoxole;1,2-Benziodoxole, 1-chloro-1,3-dihydro-3,3-dimethyl-
• CAS NO: 69352-04-1
• Molecular Formula: C₉H₁₀ClIO
• Molecular Weight: 297
• Mol File: 69352-04-1.mol
• Article Data: 20

Chemical Properties

• Melting Point: 143-145 °C(Solv: carbon tetrachloride (56-23-5))
• Appearance: /
• CAS DataBase Reference: 1-Chloro-1,3-dihydro-3,3-diMethyl-1,2-benziodoxole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Chloro-1,3-dihydro-3,3-diMethyl-1,2-benziodoxole(69352-04-1)
• EPA Substance Registry System: 1-Chloro-1,3-dihydro-3,3-diMethyl-1,2-benziodoxole(69352-04-1)

Safety Data

• Hazardous Substances Data: 69352-04-1(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 69352-04-1 differently. You can refer to the following data:
1. 1-?Chloro-?1,?3-?dihydro-?3,?3-?dimethyl-?1,?2-?benziodioxole is used as a reactant in one-pot preparation of hypervalent iodine(III)-CF3 reagent for the use in electrophilic trifluoromethylation reactions.
2. 1-Chloro-3,3-dimethylbenziodoxole is a crystalline, air-stable, yellow chloroiodane compound which finds use as a starting material for production of other hypervalent iodine compounds. It can also be used as a mild chlorinating reagent. The compound shows good solubility in polar organic solvents, typically dichloromethane or ethyl acetate.

Upstream product

• 69352-05-2 2-(2-iodophenyl)propan-2-ol 
• 610-97-9 o-iodo-methyl-benzoic acid 
• 88-67-5 2-Iodobenzoic acid 
• 75-16-1 methylmagnesium bromide 
• 134-20-3 2-carbomethoxyaniline 
• 917-64-6 methyl magnesium iodide 
• 2142-70-3 2-iodoacetophenone 

Downstream Products

• 69352-07-4 3,3-dimethyl-1-(2,2,2-trifluoro-1-phenyl-1-trifluoromethyl-ethoxy)-1,3-dihydro-1λ³-benzo[d][1,2]iodoxole 
• 69429-70-5 1-hydroxy-3,3-dimethyl-1,3-dihydro-λ³-benzo[d][1,2]iodoxole 
• 887144-97-0 Togni's reagent 
• 617-94-7 1-methyl-1-phenylethyl alcohol 
• 2142-70-3 2-iodoacetophenone 
• 187939-76-0 O-deutero-2-(2-iodophenyl)-2-propanol 
• 1391728-13-4 1-fluoro-3,3-dimethyl-1,3-dihydro-1λ³-benzo[d][1,2]iodaoxole 
• 1586794-92-4 C₁₀H₁₀INOS 
• 1584705-82-7 (((2-(2-iodophenyl)propan-2-yl)oxy)(trifluoromethyl)sulfane) 

Relevant articles and documents

Iron-Catalyzed Enantioselective Radical Carboazidation and Diazidation of α,β-Unsaturated Carbonyl Compounds

Azidation of alkenes is an efficient protocol to synthesize organic azides which are important structural motifs in organic synthesis. Enantioselective radical azidation, as a useful strategy to install a C-N3 bond, remains challenging due to the inherently instability and unique structure of radicals. Here, we disclose an efficient enantioselective radical carboazidation and diazidation of α,β-unsaturated ketones and amides catalyzed by chiral N,N′-dioxide/Fe(OTf)2 complexes. An array of substituted alkenes was transformed to the corresponding α-azido carbonyl derivatives in good to excellent enantioselectivities, benefiting the preparation of chiral α-amino ketones, vicinal amino alcohols, and vicinal diamines. Control experiments and mechanistic studies proved the radical pathway in the reaction process. The DFT calculations showed that the azido transferred to the radical intermediate via an intramolecular five-membered transition state with the internal nitrogen of the Fe-N3 species.

Oxidative cyanation of 2-oxindoles: formal total synthesis of (±)-gliocladin C

Efficient oxidative direct cyanations of 3-alkyl/aryl 2-oxindoles using Cyano-1,2-BenziodoXol-3(1H)-one (CBX) (2a) have been reported under 'transition metal-free' conditions to synthesize a wide variety of 3-cyano 3-alkyl/aryl 2-oxindoles sharing an all-carbon quaternary center under additive-free conditions. The application of this process is shown by the formal total synthesis of (±)-gliocladin C (11c) in a few steps.

Metal-Free Oxidative Cross Coupling of Indoles with Electron-Rich (Hetero)arenes

A new method for the synthesis of bi-heteroaryls is reported, based on the umpolung of indoles with benziodoxol(on)e hypervalent iodine reagents (IndoleBX). The oxidative coupling of IndoleBX with an equimolar amount of electron-rich benzenes, indoles, pyrroles, and thiophenes proceeded under mild transition-metal-free conditions. Functionalized non-symmetrical bi-indolyl heterocycles were accessed efficiently. Introduction of a new type of C2-substituted indole benziodoxole reagents further allowed extending the scope of the reaction to NH unprotected and C3-alkylated indoles. The obtained bi-heterocycles are important building blocks in synthetic and medicinal chemistry, and could be easily transformed into more complex heterocyclic systems.