Iodosobenzene diacetate, 98+%

Name: Iodosobenzene diacetate, 98+%
SKU: B24531.36

CAS: 3240-34-4 | C10H11IO4 | 322.098 g/mol

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Catalog number B24531.36

also known as B24531-36

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Chemical Identifiers

CAS3240-34-4

IUPAC Name(acetyloxy)(phenyl)-λ³-iodanyl acetate

Molecular FormulaC10H11IO4

InChI KeyZBIKORITPGTTGI-UHFFFAOYSA-N

SMILESCC(=O)O[I](OC(C)=O)C1=CC=CC=C1

Specifications

Specification Sheet

Appearance (Color)White

FormCrystals or powder or crystalline powder

Assay (Iodometric Titration)≥98.0 to ≤102.0%

Identification (FTIR)Conforms

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.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

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.

Solubility
Insoluble in water.

Notes
Light sensitive. Incompatible with strong oxidizing agents.

RUO – Research Use Only

General 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)-Benzyl oxycarbonyl-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).