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
• 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%

Properties

• Quality Segment: 200
• assay: 96%
• reaction suitability: reagent type: oxidant
• mp: 131-137 °C (lit.)
• functional group: iodo, tosylate
• 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

Description

Application

Widely used oxidant in the synthesis of various organic compounds.

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

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H315,H319
• pcodes: P264 - P280 - P302 + P352 - P305 + P351 + P338 - P332 + P313 - P337 + P313
• 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