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27126-76-7 - Hydroxy(tosyloxy)iodobenzene, 97% - HTIB - Iodosobenzene-I-mono-p-toluenesulfonate - L15701 - Alfa Aesar

L15701 Hydroxy(tosyloxy)iodobenzene, 97%

CAS Number
27126-76-7
Synonyms
HTIB
Iodosobenzene-I-mono-p-toluenesulfonate

Size Price ($) Quantity Availability
5g 36.30
25g 103.00
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Hydroxy(tosyloxy)iodobenzene, 97%

MDL
MFCD00011547
EINECS
000-000-0

Chemical Properties

Formula
C13H13IO4S
Formula Weight
392.22
Melting point
131-136°
Sensitivity
Light Sensitive

Literature References

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

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Ketones and ß-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).

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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):

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Benzylic alcohols can be oxidized to benzaldehydes in high yield under microwave irradiation: Tetrahedron Lett., 45, 4939 (2004).

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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).

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Can be used as a source of a phenyl group in the Stille coupling with organostannanes: Tetrahedron Lett., 37, 531 (1996).

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For a comprehensive review of polyvalent iodine compounds, see: Chem. Rev., 96, 1123 (1996).

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GHS Hazard and Precautionary Statements

Hazard Statements: H315-H319-H335

Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P261-P280-P305+P351+P338-P304+P340-P362-P312-P321-P405-P403+P233-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Take off contaminated clothing and wash before reuse. Call a POISON CENTER or doctor/physician if you feel unwell. Specific treatment (see label). Store locked up. Store in a well-ventilated place. Keep container tightly closed. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
2150074
Harmonized Tariff Code
2904.10
TSCA
No

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