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3240-34-4 - Iodosobenzene diacetate, 98+% - (Diacetoxyiodo)benzene - DIB - B24531 - Alfa Aesar

B24531 Iodosobenzene diacetate, 98+%

CAS Number
3240-34-4
Synonyms
(Diacetoxyiodo)benzene
DIB

Size Price ($) Quantity Availability
25g 44.70
100g 126.45
500g 508.50
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Iodosobenzene diacetate, 98+%

MDL
MFCD00008692
EINECS
221-808-1

Chemical Properties

Formula
C10H11IO4
Formula Weight
322.10
Melting point
159-161°
Sensitivity
Light Sensitive
Solubility
Insoluble in water.

Applications

Iodosobenzene is used as an oxidizing and acetoxylating agent in organic synthesis. It is actively involved in the preparation of (Z)-3,7-dimethyl-2,6-octadien-1-al(neral) from (Z)-3,7-dimethyl-2,6-octadien-1-ol (nerol) in presence of 2,2,6,6-tetramethylpiperidin-1-oxyl (TEMPO). It is a useful reagent for the synthesis of a wide variety of heterocyclic compounds. It is also used in the Pd-catalyzed 2-arylation of indoles.

Notes

Light sensitive. Incompatible with strong oxidizing agents.

Literature References

Versatile oxidizing and acetoxylating agent.

For a review of the ɑ-functionalization of carbonyl compounds by hypervalent iodine reagents, see: Contemp. Org. Synth., 2, 121 (1995).

Hydrazine hydrate is oxidized to the useful cis-reducing agent diimide: Synth. Commun., 17, 703 (1987).

Converts primary aliphatic amides to amines, by Hofmann degradation: J. Org. Chem., 44, 1746 (1979); Synthesis, 266 (1981); 31 (1983). For use in the synthesis of ß-alanine derivatives, see: J. Org. Chem., 62, 6918 (1997); for reaction scheme, see N(ɑ)-Benzyl­oxycarbonyl-L-asparagine, L08592.

In the presence of triethyl orthoformate, aryl ethyl ketones undergo a rearrangement to ɑ-methyl arylacetates: Synthesis, 231 (1984):

Similarly, in the presence of an orthoformate and sulfuric acid, flavanones undergo a 1,2-aryl shift to give 2-aryl-2,3-dihydrobenzofuran-3-carboxylates: Bull. Chem. Soc. Jpn., 68, 1168 (1995). However, iodosobenzene diacetate alone oxidizes flavanones to flavones: J. Chem. Res. (Synop.), 213 (1995). For a review of the use of the reagent in heterocyclic synthesis, see: Synlett, 221 (1994).

Useful reagent for mild, rapid cleavage of 1,3-dithianes to the parent carbonyl compounds: Syn. Commun., 30, 4081 (2000).

In combination with iodine, forms the acyl hypoiodite, which adds to alkenes: Bull. Chem. Soc. Jpn., 41, 1476 (1968), iodinates alkylbenzenes: J. Am. Chem. Soc., 90, 6187 (1968), and effects the decarboxylative iodination of aromatic carboxylic acids: Synth. Commun., 18, 1327 (1988).

See cis,cis-1,5-Cyclooctadiene, B21196, for an intramolecular cyclization reaction.

For use in the Pd(II)-catalyzed functionalization of sp2 and sp3 C-H bonds, see: J. Am. Chem. Soc., 126, 2300 (2004).

Treatment with aqueous NaOH gives the useful selective oxidant iodosobenzene (iodosylbenzene): Org. Synth. Coll., 5, 658 (1973).

For a brief feature on uses of the reagent in synthesis, see: Synlett, 657 (2006). For reviews of the use of polyvalent iodine compounds in organic synthesis, see: Synthesis, 709 (1984); Acc. Chem. Res., 19, 244 (1986); Chem. Rev., 96, 1123 (1996). For a monograph, see: A Varvoglis, The Organic Chemistry of Polycoordinated Iodine, VCH, N.Y. (1992).

Wu, J.; Hoang, K. L. M.; Leow, M. L.; Liu, X. W. Pd-catalyzed cross-coupling of aromatic compounds with carboxylic acids via C-H bond activation. Org. Chem. Front. 2015, 2 (5), 502-505.

Ghosh, S.; Chaudhuri, S.; Bisai, A. Oxidative Dimerization of 2-Oxindoles Promoted by KO t Bu-I2: Total Synthesis of (±)-Folicanthine. Org. Lett. 2015, 17 (6), 1373-1376.

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
1879369
Harmonized Tariff Code
2931.90
TSCA
Yes
RTECS
DA3525000

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