69180-49-0

Basic information

• Product Name: bis(acetyloxy)(2-methoxyphenyl)-lambda~3~-iodane
• CAS NO: 69180-49-0
• Molecular Formula: C₁₁H₁₃IO₅
• Molecular Weight: 352.1224
• Mol File: 69180-49-0.mol
• Article Data: 18

Chemical Properties

• CAS DataBase Reference: bis(acetyloxy)(2-methoxyphenyl)-lambda~3~-iodane(CAS DataBase Reference)
• NIST Chemistry Reference: bis(acetyloxy)(2-methoxyphenyl)-lambda~3~-iodane(69180-49-0)
• EPA Substance Registry System: bis(acetyloxy)(2-methoxyphenyl)-lambda~3~-iodane(69180-49-0)

Safety Data

• Hazardous Substances Data: 69180-49-0(Hazardous Substances Data)

Upstream product

• 529-28-2 4-iodoanisol 
• 64-19-7 acetic acid 
• 2754-27-0 trimethylsilyl acetate 
• 533-58-4 2-Iodophenol 
• 79-21-0 peracetic acid 
• 108-24-7 acetic anhydride 

Downstream Products

• 73234-87-4 1-methoxy-2(2-propynyl)benzene 
• 139553-91-6 2-Iodo-1-methoxy-3-prop-2-ynyl-benzene 
• 1039396-23-0 (E)-3-((2-methoxyphenyl)(phenyl)methylene)-1-methylindolin-2-one 
• 1379474-24-4 dimethyl 2-((2-methoxyphenyl)-λ³-iodanylidene)malonate 
• 1404368-06-4 C₁₅H₁₇IO₃ 
• 1404368-10-0 2-iodo-3-(2-methoxyphenoxy)-5,5-dimethylcyclohex-2-enone 

Relevant articles and documents

Iodine(III) Reagent-Mediated Intramolecular Amination of 2-Alkenylanilines to Prepare Indoles

A variety of 3-substituted and 2,3-disubstituted indoles were synthesized efficiently in good yields through the intramolecular amination of 2-alkenylanilines promoted by readily available iodine(III) reagents in a short reaction time. Mechanistic studies showed that the reaction pathway went through a nitrenium ion and that 3-acetoxy indoline was the key intermediate in the indole formation. The indole product was easily prepared on a gram scale and amination also proceeded smoothly using catalytic 3,5-dimethylphenyl iodine in the presence of mCPBA. Furthermore, the indolo[3,2-a]carbazole scaffold was prepared in good yield in six steps from commercial ortho-iodoaniline. (Figure presented.).

Generation of Aryl Radicals through Reduction of Hypervalent Iodine(III) Compounds with TEMPONa: Radical Alkene Oxyarylation

A novel method for selective generation of aryl radicals from diaryliodonium salts and iodanylidene malonates with sodium 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPONa) as a single-electron transfer (SET) reducing reagent is described. In the presence of various alkenes, aryl radicals formed after SET-reduction of hypervalent iodine compounds undergo alkene addition and the adduct radicals that are thus generated are efficiently trapped by the concomitantly generated TEMPO radical to eventually afford oxyarylated products in moderate to very good yields. The efficiency of aryl radical generation of various iodine(III) reagents is studied and the generation of an iodanylidene malonate aryl radical is also investigated by computational methods.

Synthesis of ionic-liquid-supported diaryliodonium salts

The synthesis of ionic-liquid-supported diaryliodonium salts is described. The synthesis is simple and practical, and the ionic liquid products require no chromatographic purification. The ionic-liquid-supported diaryliodonium salts are quite stable, and they did not show any sign of decomposition or loss of reactivity, even after being stored for one month at 5 °C. The reactivity of these salts was explored in the phenylation of substituted phenols and carboxylic acids, and the corresponding diaryl ethers and aryl esters, respectively, were synthesized in good to excellent yields and with high purities.