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301035

Sigma-Aldrich

[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
Beilstein:
2150074
MDL number:
MFCD00011547
UNSPSC Code:
12352002
PubChem Substance ID:
24858159
NACRES:
NA.22

Assay

96%

reaction suitability

reagent type: oxidant

mp

131-137 °C (lit.)

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

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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

Signal Word

Warning

Hazard Statements

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Kumar, R.
Synlett, 2764-2764 (2007)
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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