Basic information Safety Supplier Related

[Hydroxy(tosyloxy)iodo]benzene

Basic information Safety Supplier Related

[Hydroxy(tosyloxy)iodo]benzene Basic information

Product Name:
[Hydroxy(tosyloxy)iodo]benzene
Synonyms:
  • Iodine,hydroxy(4-Methylbenzenesulfonato-kO)phenyl-
  • [Hydroxy(tosyloxy)iodo]benzene 96%
  • [Hydroxy(4-toluenesulfonato)iodo]benzene
  • Hydroxy(phenyl)iodo tosylate
  • [Hydroxy(tosyloxy)iodo]benzene≥ 98%(Titration)
  • Hydroxy{[(4-methylphenyl)sulfonyl]oxy} phenyliodine
  • Koser's Regent ,HTIB
  • Hydroxyl(toluenesulfonyloxygengeneration)iodobenzene
CAS:
27126-76-7
MF:
C13H13IO4S
MW:
392.21
EINECS:
629-501-8
Product Categories:
  • Hypervalent Iodine Compounds
  • Oxidation
  • Synthetic Organic Chemistry
  • Phenyls & Phenyl-Het
Mol File:
27126-76-7.mol
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[Hydroxy(tosyloxy)iodo]benzene Chemical Properties

Melting point:
131-137 °C (lit.)
storage temp. 
Keep in dark place,Inert atmosphere,Room temperature
solubility 
soluble in Methanol
form 
Crystalline Powder
pka
7.59±0.58(Predicted)
color 
Pale yellow
Sensitive 
Light Sensitive
Merck 
14,5321
BRN 
2150074
InChIKey
LRIUKPUCKCECPT-UHFFFAOYSA-N
CAS DataBase Reference
27126-76-7(CAS DataBase Reference)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/38
Safety Statements 
26-36
WGK Germany 
3
8
HazardClass 
IRRITANT
HS Code 
29039990

MSDS

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[Hydroxy(tosyloxy)iodo]benzene Usage And Synthesis

Chemical Properties

Pale yellow crystalline powder

Uses

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 ?-hydroxyketoximes via oxidative N-O coupling
  • Ring expansion in synthesis of aminopeptidase inhibitors
  • Oxidation and protonation reactions in acidic conditions

Uses

Versatile synthetic reagent in phenyliodination and/or tosylation of a range of organic substrates; in oxidative transformations including oxidative rearrangements.

Purification Methods

Possible impurities are tosic acid (removed by washing with Me2CO) and acetic acid (removed by washing with Et2O). It is purified by dissolving in the minimum volume of MeOH, adding Et2O to cloud point and setting aside for the prisms to separate [Koser & Wettach J Org Chem 42 1476 1977, NMR: Koser et al. J Org Chem 41 3609 1976]. It has also been crystallised from CH2Cl2 (needles, m 140-142o) [Neiland & Karele J Org Chem, USSR (Engl Transl) 6 889 1970].

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