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301035 Sigma-Aldrich

[Hydroxy(tosyloxy)iodo]benzene

96%

Synonym: 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

  • CAS Number 27126-76-7

  • Linear Formula CH3C6H4SO3I(OH)C6H5

  • Molecular Weight 392.21

  •  Beilstein/REAXYS Number 2150074

  •  MDL number MFCD00011547

  •  PubChem Substance ID 24858159

  •  NACRES NA.22

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Properties

Related Categories Chemical Synthesis, Hypervalent Iodine, Oxidizing Agents, Synthetic Reagents
assay   96%
mp   131-137 °C (lit.)
storage temp.   room temp
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

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.

Packaging

5, 25 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable
Protocols & Articles
Peer-Reviewed Papers
15

References

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