hydroxy phenyl 4-methylbenzene-1-sulfonoperoxoyl iodide

• ChemBase ID: 32051
• Molecular Formular: C13H13IO4S
• Molecular Mass: 392.20939
• Monoisotopic Mass: 391.9579279
• 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

NAMES AND DATABASE IDS

Names

• 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

Database IDs

• 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

• Acid pKa: 12.725231
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.158997
• LogD (pH = 7.4): 4.158995
• Log P: 4.158997
• Molar Refractivity: 81.887 cm^3
• Polarizability: 33.725174 Å^3
• Polar Surface Area: 63.6 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 131-136°C; 131-136°C; 131-137 °C; 131-137 °C(lit.); 134 - 136°C
• Hydrophobicity(logP): 2.431

Safety Information

• Storage Warning: IRRITANT; Irritant; Light Sensitive
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38; 36/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319; H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A; P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥97.0% (AT); 95%; 96%; 97%
• Grade: purum
• Linear Formula: CH3C6H4SO3I(OH)C6H5

DETAILS

Sigma Aldrich - 301035

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

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

• 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).