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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%

Número CAS
27126-76-7
Nombre Alternativo
HTIB
Iodosobenzene-I-mono-p-toluenesulfonate

Tamaño Precio ($) Cantidad Disponibilidad
5g 36,30
25g 103,00
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Hydroxy(tosyloxy)iodobenzene, 97%

MDL
MFCD00011547
EINECS
000-000-0

Propiedades químicas

Fórmula
C13H13IO4S
Peso molecular
392.22
Punto de fusión
131-136°
Sensibilidad
Light Sensitive

Referencias documentales

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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Indicaciones de peligro y de precaución del GHS

Indicaciones de peligro (UE): H315-H319-H335

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

Indicaciones de precaución: P261-P280a-P305+P351+P338-P304+P340-P405-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/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. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Otras referencias

Beilstein
2150074
Código de tarifa arancelaria unificado
2907.29
TSCA
No

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