(acetyloxy)(phenyl)-$l^{3}-iodanyl acetate

• ChemBase ID: 91440
• Molecular Formular: C10H11IO4
• Molecular Mass: 322.09641
• Monoisotopic Mass: 321.97020683
• SMILES: [I](c1ccccc1)(OC(=O)C)OC(=O)C
• Canonical SMILES: CC(=O)O[I](c1ccccc1)OC(=O)C
• InChI: InChI=1S/C10H11IO4/c1-8(12)14-11(15-9(2)13)10-6-4-3-5-7-10/h3-7H,1-2H3
• InChIKey: ZBIKORITPGTTGI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (acetyloxy)(phenyl)-$l^{3}-iodanyl acetate; (acetyloxy)(phenyl)-λ^3-iodanyl acetate
• IUPAC Traditional name: phenyliodosodiacetate; (acetyloxy)(phenyl)-λ^3-iodanyl acetate
• Synonyms: (Diacetoxyiodo)benzene; Iodobenzene diacetate; (acetyloxy)(phenyl)-$l^{3}-iodanyl acetate; (Diacetoxyiodo)benzene; DIB; Iodosobenzene diacetate; Iodobenzene I,I-diacetate; Iodosobenzene I,I-diacetate; (Diacetoxyiodo)benzene; 二乙酸亚碘酰苯; 二乙酸亚碘酰苯; 碘苯二乙酸酯; 碘苯二乙酸

Database IDs

• CAS Number: 3240-34-4
• EC Number: 221-808-1
• MDL Number: MFCD00008692
• Beilstein Number: 1879369
• PubChem SID: 24858980; 24850764; 162078139
• PubChem CID: 76724

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.1789038
• LogD (pH = 7.4): 2.1789038
• Log P: 2.1789038
• Molar Refractivity: 62.2473 cm^3
• Polarizability: 25.908724 Å^3
• Polar Surface Area: 52.6 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 159-161°C; 159-163°C; 161-163 °C; 161-163 °C(lit.)

Safety Information

• Storage Warning: Irritant/Light Sensitive/Keep Cold; Light Sensitive
• RTECS: DA3525000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (AT); 96%; 98%; 98+%
• Grade: purum
• Linear Formula: C6H5I(O2CCH3)2

DETAILS

Sigma Aldrich - 178721

Application
Stoichiometric oxidant in the TEMPO oxidation of nerol to neral.1 Oxidant employed in the rhodium-catalyzed aziridination of olefins with sulfamate esters.2
Unactivated sp3 C-H bonds of both oxime and pyridine substrates undergo highly regio- and chemoselective Pd(II)-catalyzed oxygenation with PhI(OAc)2 as a stoichiometric oxidant.
Used in the room temperature Pd-catalyzed 2-arylation of indoles
Useful reagent for the synthesis of a wide variety of heterocyclic compounds.
Rh2(esp)2: An Exceptionally Efficient and Selective Catalyst for C-H Amination
Packaging
1 kg in glass bottle
5, 25, 100 g in glass bottle

Sigma Aldrich - 31490

Other Notes
Reagent for the cleavage of vic-glycols, hydroxylations and many other oxidation reactions, review1; Preparation of the thermally unstable iodosobenzene2
Application
Rh2(esp)2: An Exceptionally Efficient and Selective Catalyst for C-H Amination

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 ?-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).