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Merck
CN

56517

[Hydroxy(tosyloxy)iodo]benzene

purum, ≥97.0% (AT)

Synonym(s):

HTIB, Hydroxy(4-methylbenzenesulfonato-O)phenyliodine, Hydroxy(phenyl)iodo tosylate, Iodosobenzene-I-mono-p-toluenesulfonate, Koser’s reagent, NSC 294176, Phenyliodosyl hydroxide tosylate, [Hydroxy(4-toluenesulfonato)iodo]benzene

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About This Item

Linear Formula:
CH3C6H4SO3I(OH)C6H5
CAS Number:
Molecular Weight:
392.21
UNSPSC Code:
12352000
Beilstein/REAXYS Number:
2150074
MDL number:
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grade

purum

assay

≥97.0% (AT)

reaction suitability

reagent type: oxidant

mp

131-137 °C

SMILES string

Cc1ccc(cc1)S(=O)(=O)O[I](O)c2ccccc2

InChI

1S/C13H13IO4S/c1-11-7-9-13(10-8-11)19(16,17)18-14(15)12-5-3-2-4-6-12/h2-10,15H,1H3

InChI key

LRIUKPUCKCECPT-UHFFFAOYSA-N

Application

Reactant for:
  • Ligand-free palladium-catalyzed Heck-type coupling reactions
  • Preparation of carbodiimides via dehydrosulfurization of thioureas
  • Preparation of nitriles by oxidative conversion of alcohols, aldehydes, and amines
  • Preparation of substituted anilines via aromatic aldoxime reaction
  • Preparation of tetrahydrofurans by oxidative cyclization of homoallylic alcohols
  • Preparation of isoxazoline N-Oxides from β-hydroxyketoximes via oxidative N-O coupling
  • Ring expansion in synthesis of aminopeptidase inhibitors
  • Oxidation and protonation reactions in acidic conditions

Other Notes

Reagent for the selective syn-1,2-ditosyloxylation of alkenes, tosyloxylation reactions and other transformations

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class

13 - Non Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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G.F. Koser et al.
Aldrichimica Acta, 34, 89-89 (2001)
O. Prakash et al.
Heterocycles, 38, 409-409 (1994)
R.M. Moriarty et al.
Synlett, 365-365 (1990)

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