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Merck
CN

301035

[Hydroxy(tosyloxy)iodo]benzene

96%

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:
27126-76-7
Molecular Weight:
392.21
UNSPSC Code:
12352002
NACRES:
NA.22
PubChem Substance ID:
24858159
MDL number:
MFCD00011547
Beilstein/REAXYS Number:
2150074
Assay:
96%

Key Documents

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Product Name

[Hydroxy(tosyloxy)iodo]benzene, 96%

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

SMILES string

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

InChI key

LRIUKPUCKCECPT-UHFFFAOYSA-N

assay

96%

reaction suitability

reagent type: oxidant

mp

131-137 °C (lit.)

functional group

iodo
tosylate

Quality Level

200

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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 ß-hydroxyketoximes via oxidative N-O coupling
  • Ring expansion in synthesis of aminopeptidase inhibitors
  • Oxidation and protonation reactions in acidic conditions
Widely used oxidant in the synthesis of various organic compounds.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCC4417
BCCB0588
BCBN7235V
BCBF6164V
BCBH3258V

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Kumar, R.
Synlett, 2764-2764 (2007)
S Tuuli Karhu et al.
Archives of toxicology (2018-07-11)
Safety assessment of drug candidates in numerous in vitro and experimental animal models is expensive, time consuming and animal intensive. More thorough toxicity profiling already in the early drug discovery projects using human cell models, which more closely resemble the
Damian Tarasek et al.
Bioorganic chemistry, 97, 103692-103692 (2020-03-11)
p-Diphenols, such as homogentisic acid, gentisic acid, etamsylate, and calcium dobesilate, interfere with diagnostic tests utilizing the Trinder reaction but the mechanisms of these effects are not fully understood. We observed substantial differences both in oxidation of p-diphenols by horseradish

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