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

B24531 Iodosobenzene diacetate, 98+%

CAS Number

Size Price ($) Quantity Availability
25g 50.70
100g 134.00
500g 571.00
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Iodosobenzene diacetate, 98+%


Chemical Properties

Formula Weight
Melting point
Light Sensitive
Insoluble in water.


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.


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-P280a-P305+P351+P338-P304+P340-P312a-P321-P332+P313-P405-P403+P233-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. Specific treatment (see label). If skin irritation occurs: Get medical advice/attention. 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.

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