[Hydroxy(tosyloxy)iodo]benzene

Base Information

• Chemical Name: [Hydroxy(tosyloxy)iodo]benzene
• CAS No.: 27126-76-7
• Molecular Formula: C13H13IO4S
• Molecular Weight: 392.214
• Hs Code.: 29039990
• European Community (EC) Number: 629-501-8
• NSC Number: 294176
• UNII: 2EOA97B14A
• DSSTox Substance ID: DTXSID10315359
• Nikkaji Number: J208.907F
• Wikidata: Q27254634
• Mol file: 27126-76-7.mol

Synonyms:(hydroxy(tosyloxy)iodo)benzene;HTIB cpd

Chemical Property of [Hydroxy(tosyloxy)iodo]benzene

Chemical Property:

• Appearance/Colour: Pale yellow crystalline powder
• Melting Point: 131-137 °C(lit.)
• PKA: 7.59±0.58(Predicted)
• PSA: 71.98000
• LogP: 4.35980
• Storage Temp.: Refrigerator (+4°C)
• Sensitive.: Light Sensitive
• Solubility.: soluble in Methanol
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 391.95793
• Heavy Atom Count: 19
• Complexity: 365

Purity/Quality:

98%, ^*data from raw suppliers

[Hydroxy(tosyloxy)iodo]benzene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)OI(C2=CC=CC=C2)O
• Uses: Versatile synthetic reagent in phenyliodination and/or tosylation of a range of organic substrates; in oxidative transformations including oxidative rearrangements. Reactant for:Ligand-free palladium-catalyzed Heck-type coupling reactionsPreparation of carbodiimides via dehydrosulfurization of thioureasPreparation of nitriles by oxidative conversion of alcohols, aldehydes, and aminesPreparation of substituted anilines via aromatic aldoxime reactionPreparation of tetrahydrofurans by oxidative cyclization of homoallylic alcoholsPreparation of isoxazoline N-Oxides from ?-hydroxyketoximes via oxidative N-O couplingRing expansion in synthesis of aminopeptidase inhibitorsOxidation and protonation reactions in acidic conditions

Technology Process of [Hydroxy(tosyloxy)iodo]benzene

There total 18 articles about [Hydroxy(tosyloxy)iodo]benzene 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: 100.0%

[bis(acetoxy)iodo]benzene (3240-34-4) + toluene-4-sulfonic acid (104-15-4) → [hydroxy(tosyloxy)iodo]benzene (27126-76-7)

Guidance literature:

In acetonitrile;

DOI:10.1002/anie.201209007

Reference yield: 99.0%

iodobenzene (591-50-4) + toluene-4-sulfonic acid (104-15-4) → [hydroxy(tosyloxy)iodo]benzene (27126-76-7)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In chloroform; at 20 ℃; for 2h;

DOI:10.1055/s-2005-872697

Reference yield: 98.0%

[bis(acetoxy)iodo]benzene (3240-34-4) + p-toluenesulfonic acid monohydrate (6192-52-5) → [hydroxy(tosyloxy)iodo]benzene (27126-76-7)

Guidance literature:

for 0.00555556h; Microwave irradiation; neat (no solvent);

DOI:10.3184/030823409X396427

upstream raw materials:

iodobenzene

(hydroxy(tosyloxy)iodo)pentafluorobenzene

benzene

[bis(acetoxy)iodo]benzene

Downstream raw materials:

2-thienylphenyliodonium tosylate

phenyl(5-bromo-2-thienyl)iodonium tosylate

Toluene-4-sulfonate(5-iodo-thiophen-2-yl)-phenyl-iodonium;

phenyl(5-ethyl-2-thienyl)iodonium tosylate

Refernces

• 1、 Stang,P.J.,Surber,B.W.. "-". . p. 1452. Retrieved 1985.
• 2、 Wang, Chenyang,Ma, Ding,Tu, Yongliang,Bolm, Carsten. "Use of hypervalent iodine reagents in visible light-promoted α-ketoacylations of sulfoximines with aryl alkynes". . p. 8937 - 8940. Retrieved 2020.
• 3、 -. "SYNTHESIS OF HYPERVALENT IODINE REAGENTS WITH DIOXYGEN". Paragraph 0085-0086. . Retrieved 2019/01/15.