Hydroxy(tosyloxy)iodobenzene

• Catalog No.: L15701
• CAS Number: 27126-76-7
• M. F.: C13H13IO4S
• M. W.: 392.20939
• Purity: 97%

SYNONYMS

• Title: 羟基(甲苯磺酰氧代)碘苯
• IUPAC name: hydroxy phenyl 4-methylbenzene-1-sulfonoperoxoyl iodide
• IUPAC Traditional name: hydroxy phenyl 4-methylbenzenesulfonoperoxoyl iodide
• Synonyms: HTIB; Iodosobenzene-I-mono-p-toluenesulfonate

DATABASE IDS

• CAS Number: 27126-76-7
• EC Number: 000-000-0
• MDL Number: MFCD00011547
• Beilstein Number: 2150074

PROPERTIES

• Purity: 97%
• Melting Point: 131-136°C
• GHS Hazard statements: H315-H319-H335
• European Hazard Symbols: Irritant (Xi)
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• Storage Warning: Light Sensitive
• TSCA Listed: 否

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).