IODOSOBENZENE

Base Information

• Chemical Name: IODOSOBENZENE
• CAS No.: 536-80-1
• Deprecated CAS: 125509-11-7,1056742-46-1,1056743-13-5,1015765-81-7,1056742-46-1,1056743-13-5
• Molecular Formula: C6H5 I O
• Molecular Weight: 220.01
• Hs Code.: 2903999090
• European Community (EC) Number: 208-648-8
• NSC Number: 406477
• UNII: TWW7V7Q50P
• DSSTox Substance ID: DTXSID1060213
• Nikkaji Number: J6.356H
• Wikipedia: Iodosobenzene
• Wikidata: Q2179522
• Mol file: 536-80-1.mol

Synonyms:Benzene,iodoso- (6CI,7CI,8CI); Iodosobenzene; Iodosylbenzene; NSC 406477

Chemical Property of IODOSOBENZENE

Chemical Property:

• Melting Point: 210°C (rough estimate)
• PSA: 17.07000
• Density: 1.8665 (estimate)
• LogP: 2.17240
• Storage Temp.: Freezer
• Water Solubility.: Slightly soluble in water
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 219.93851
• Heavy Atom Count: 8
• Complexity: 76.6

Purity/Quality:

98%,99%, ^*data from raw suppliers

Iodosobenzene ^*data from reagent suppliers

Safty Information:

• Safety Statements: 17-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Halogenated Monoaromatics
• Canonical SMILES: C1=CC=C(C=C1)I=O
• Uses: Oxygen transfer reagent for stiochiometric or catalytic cross-functionalization of alkenes, alcohols, sulfides, and organometallo Compounds.Iodosobenzene is used as an oxidizing and acetoxylating agent in organic synthesis. It is actively involved in the preparation of (Z)-3,7-dimethyl-2,6-octadien-1-al(neral) from (Z)-3,7-dimethyl-2,6-octadien-1-ol (nerol) in presence of 2,2,6,6-tetramethylpiperidin-1-oxyl (TEMPO). It is a useful reagent for the synthesis of a wide variety of heterocyclic compounds. It is also used in the Pd-catalyzed 2-arylation of indoles. lodosobenzene is a relatively new, selective oxidizing agent which is particularly useful for the preparation of sulfoxides from unsaturated or otherwise sensitive sulfides. The preparation of diallyl, di-2-hydroxyethyl and phenyl 2-chloroethyl sulfoxides illustrates its use.Iodosobenzene diacetate behaves similarly and oxidizes diphenyl and 4-nitro-phenyl 4'-carboxyphenyl sulfide exclusively to the sulfoxides. This reagent failed, however, to oxidize bis(2-nitro-4-trifuoromethylphenyl) sulfide and in the case of bis(2-aminophenyl) sulfide it gave complex products. Iodosobenzene diacetate caused diacetoxylation of the heterocycle of 2,5-diphenyl-1 ,4-dithiadiene rather than oxidation of the sulfide function, and with 2,5-diphenylI-1 ,4-dithiadiene-1-oxide unexpected results were obtained, as discussed in section C-4.Organic Sulfur Compounds

Technology Process of IODOSOBENZENE

There total 21 articles about IODOSOBENZENE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

bis(acetoxy)iodylbenzene (16975-78-3) → iodosylbenzene (536-80-1)

Guidance literature:

With sodium hydroxide; for 0.75h;

DOI:10.1039/d1cc04521k

Reference yield: 80.0%

iodobenzene (591-50-4) → iodosylbenzene (536-80-1)

Guidance literature:

With water; lithium perchlorate; In 2,2,2-trifluoroethanol; at 20 ℃; for 1.5h; Solvent; Electrochemical reaction;

DOI:10.1002/cjoc.202000501

Reference yield: 73.0%

(Dichloroiodo)benzene (932-72-9) → iodosylbenzene (536-80-1)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran;

upstream raw materials:

iodobenzene

(Dichloroiodo)benzene

[bis(acetoxy)iodo]benzene

iodoxybenzene

Downstream raw materials:

phenyl-[2]thienyl-iodonium ; chloride

Phenyl vinyl sulfoxide

(dibenzoyloxyiodo)benzene

1-phenyl-1λ³-[1,2,7]iodadioxepane-3,6-dione

Refernces

• 1、 Zhao, Ying,Yan, Haiming,Lu, Hanwei,Huang, Zhiliang,Lei, Aiwen. "Para -Selective C-H bond functionalization of iodobenzenes". . p. 11366 - 11369. Retrieved 2016.
• 2、 Bera, Shyamal Kanti,Alam, Md Toufique,Mal, Prasenjit. "C-N Coupling via Antiaromatic Endocyclic Nitrenium Ions". . p. 12009 - 12020. Retrieved 2019.
• 3、 Zu, Bing,Ke, Jie,Guo, Yonghong,He, Chuan. "Synthesis of Diverse Aryliodine(III) Reagents by Anodic Oxidation?". supporting information. p. 627 - 632. Retrieved 2021/02/12.
• 4、 Vo, Nhat Tam,Herrero, Christian,Guillot, Régis,Inceoglu, Tanya,Leibl, Winfried,Clémancey, Martin,Dubourdeaux, Patrick,Blondin, Geneviève,Aukauloo, Ally,Sircoglou, Marie. "Intercepting a transient non-hemic pyridine: N -oxide Fe(iii) species involved in OAT reactions". supporting information. p. 12836 - 12839. Retrieved 2021/12/10.