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27126-76-7 molecular structure
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hydroxy phenyl 4-methylbenzene-1-sulfonoperoxoyl iodide

ChemBase ID: 32051
Molecular Formular: C13H13IO4S
Molecular Mass: 392.20939
Monoisotopic Mass: 391.9579279
SMILES and InChIs

SMILES:
S(=O)(=O)(O[I](c1ccccc1)O)c1ccc(cc1)C
Canonical SMILES:
Cc1ccc(cc1)S(=O)(=O)O[I](c1ccccc1)O
InChI:
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
InChIKey:
LRIUKPUCKCECPT-UHFFFAOYSA-N

Cite this record

CBID:32051 http://www.chembase.cn/molecule-32051.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
hydroxy phenyl 4-methylbenzene-1-sulfonoperoxoyl iodide
IUPAC Traditional name
hydroxy phenyl 4-methylbenzenesulfonoperoxoyl iodide
Synonyms
Iodosobenzene-I-mono-p-toluenesulfonate
Koser's Reagent
Hydroxy(tosyloxy)iodobenzene
HTIB
Hydroxy(phenyl)iodo tosylate
NSC 294176
Phenyliodosyl hydroxide tosylate
[Hydroxy(4-toluenesulfonato)iodo]benzene
Hydroxy(4-methylbenzenesulfonato-O)phenyliodine
Koser’s reagent
[Hydroxy(tosyloxy)iodo]benzene
hydroxy phenyl 4-methylbenzene-1-sulfonoperoxoyl iodide
Hydroxy(tosyloxy)iodobenzene
[Hydroxy(tosyloxy)iodo]benzene
Koser 试剂
羟基(甲苯磺酰氧代)碘苯
羟基甲苯磺酰碘苯
羟基(甲苯磺酰氧代)碘苯
CAS Number
27126-76-7
EC Number
000-000-0
MDL Number
MFCD00011547
Beilstein Number
2150074
PubChem SID
24858159
160995358
PubChem CID
325434

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 12.725231  H Acceptors
H Donor LogD (pH = 5.5) 4.158997 
LogD (pH = 7.4) 4.158995  Log P 4.158997 
Molar Refractivity 81.887 cm3 Polarizability 33.725174 Å3
Polar Surface Area 63.6 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Melting Point
131-136°C expand Show data source
131-136°C expand Show data source
131-137 °C expand Show data source
131-137 °C(lit.) expand Show data source
134 - 136°C expand Show data source
Hydrophobicity(logP)
2.431 expand Show data source
Storage Warning
IRRITANT expand Show data source
Irritant expand Show data source
Light Sensitive expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
36/37/38 expand Show data source
36/38 expand Show data source
Safety Statements
26-36 expand Show data source
26-37 expand Show data source
TSCA Listed
false expand Show data source
expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H315-H319 expand Show data source
H315-H319-H335 expand Show data source
GHS Precautionary statements
P261-P305+P351+P338-P302+P352-P321-P405-P501A expand Show data source
P305 + P351 + P338 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Purity
≥97.0% (AT) expand Show data source
95% expand Show data source
96% expand Show data source
97% expand Show data source
Grade
purum expand Show data source
Linear Formula
CH3C6H4SO3I(OH)C6H5 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - 301035 external link
Application
Widely used oxidant in the synthesis of various organic compounds.9
Reactant for:
• Ligand-free palladium-catalyzed Heck-type coupling reactions1
• Preparation of carbodiimides via dehydrosulfurization of thioureas2
• Preparation of nitriles by oxidative conversion of alcohols, aldehydes, and amines3
• Preparation of substituted anilines via aromatic aldoxime reaction4
• Preparation of tetrahydrofurans by oxidative cyclization of homoallylic alcohols5
• Preparation of isoxazoline N-Oxides from β-hydroxyketoximes via oxidative N-O coupling6
• Ring expansion in synthesis of aminopeptidase inhibitors7
• Oxidation and protonation reactions in acidic conditions8
Packaging
5, 25 g in glass bottle
Sigma Aldrich - 56517 external link
Other Notes
Reagent for the selective syn-1,2-ditosyloxylation of alkenes, tosyloxylation reactions and other transformations 9,10,11
Application
Reactant for:
• Ligand-free palladium-catalyzed Heck-type coupling reactions1
• Preparation of carbodiimides via dehydrosulfurization of thioureas2
• Preparation of nitriles by oxidative conversion of alcohols, aldehydes, and amines3
• Preparation of substituted anilines via aromatic aldoxime reaction4
• Preparation of tetrahydrofurans by oxidative cyclization of homoallylic alcohols5
• Preparation of isoxazoline N-Oxides from β-hydroxyketoximes via oxidative N-O coupling6
• Ring expansion in synthesis of aminopeptidase inhibitors7
• Oxidation and protonation reactions in acidic conditions8

REFERENCES

REFERENCES

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  • • Ketones and ?-dicarbonyl compounds give the ɑ-tosyloxy derivatives: J. Org. Chem., 47, 2487 (1982); see also Synth. Commun., 32, 1875 (2002). For a review of the ɑ-functionalization of carbonyl compounds by hypervalent iodine reagents, see: Contemp. Org. Synth., 2, 121 (1995). Reaction rates are increased by sonication: Tetrahedron Lett., 33, 7647 (1992). Flavanones undergo oxidative rearrangement to isoflavones: Synlett, 337 (1990). For a review of the use of the reagent in heterocyclic synthesis, see: Synlett, 221 (1994).
  • • Alkenes are converted to cis-1,2-ditosyloxyalkanes: J. Org. Chem., 49, 2462 (1984). Unconjugated alkenoic acids undergo cyclization to tosyloxy lactones: Tetrahedron Lett., 27, 4557 (1984); alkenedioic acids give bis-lactones with cis stereoselectivity: Tetrahedron Lett., 27, 5437 (1984):
  • • Benzylic alcohols can be oxidized to benzaldehydes in high yield under microwave irradiation: Tetrahedron Lett., 45, 4939 (2004).
  • • Sulfides are oxidized to sulfoxides in high yields: Synth. Commun., 27, 1315 (1997). In refluxing acetonitrile, alkyl amides are converted to amine tosylates: J. Org. Chem., 51, 2669 (1986), giving better yields from long-chain amides than the classical Hofmann and Curtius methods: J. Org. Chem., 53, 5158 (1988).
  • • Can be used as a source of a phenyl group in the Stille coupling with organostannanes: Tetrahedron Lett., 37, 531 (1996).
  • • For a comprehensive review of polyvalent iodine compounds, see: Chem. Rev., 96, 1123 (1996).
  • • Reagent for ɑ-tosyloxylation of various functional groups; review: Synlett, 337 (1990).
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PATENTS

PATENTS

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INTERNET

INTERNET

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