CAS 27126-76-7|hydroxy phenyl 4-methylbenzenesulfonoperoxoyl iodide|hydroxy phenyl 4-methylbenzene-1-sulfonoperoxoyl iodide|Hydroxy(tosyloxy)iodobenzene|hydroxy phenyl 4-methylbenzene-1-sulfonoperox...

General Information

Structure

Molecular Formula

C₁₃H₁₃IO₄S

Molecular Mass

392.20939

Exact Mass

391.9579279

Charge

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

Canonic Smiles

Cc1ccc(cc1)S(=O)(=O)O[I](c1ccccc1)O

Isomeric Smiles

S(=O)(=O)(O[I](c1ccccc1)O)c1ccc(cc1)C

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

Polarizability

33.725174

Polar Surface Area

63.6

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

IUPAC Traditional name

hydroxy phenyl 4-methylbenzenesulfonoperoxoyl iodide

IUPAC name

hydroxy phenyl 4-methylbenzene-1-sulfonoperoxoyl iodide

Synonyms

Hydroxy(tosyloxy)iodobenzenehydroxy phenyl 4-methylbenzene-1-sulfonoperoxoyl iodideIodosobenzene-I-mono-p-toluenesulfonateKoser 试剂[Hydroxy(4-toluenesulfonato)iodo]benzeneHTIBNSC 294176[Hydroxy(tosyloxy)iodo]benzenePhenyliodosyl hydroxide tosylate羟基(甲苯磺酰氧代)碘苯羟基(甲苯磺酰氧代)碘苯羟基甲苯磺酰碘苯Koser’s reagentHydroxy(4-methylbenzenesulfonato-O)phenyliodineHydroxy(phenyl)iodo tosylateHydroxy(tosyloxy)iodobenzeneKoser's Reagent[Hydroxy(tosyloxy)iodo]benzene

Names and Identifiers

Registration numbers

CAS Number

MDL Number

Beilstein Number

PubChem SID

PubChem CID

EC Number

Registration numbers

Properties

Related Proteins

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Molecular Spectra

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Molecule 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

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

Molecule Details

References

PubChem Literature

From Data Sources

• 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).

• Reagent for ɑ-tosyloxylation of various functional groups; review: Synlett, 337 (1990).

• 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):

• 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).

• 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).

References

Bioactivity

PubChem BioAssay

Bioactivity