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3240-34-4 molecular structure
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(acetyloxy)(phenyl)-$l^{3}-iodanyl acetate

ChemBase ID: 91440
Molecular Formular: C10H11IO4
Molecular Mass: 322.09641
Monoisotopic Mass: 321.97020683
SMILES and InChIs

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

Cite this record

CBID:91440 http://www.chembase.cn/molecule-91440.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(acetyloxy)(phenyl)-$l^{3}-iodanyl acetate
(acetyloxy)(phenyl)-λ3-iodanyl acetate
IUPAC Traditional name
phenyliodosodiacetate
(acetyloxy)(phenyl)-λ3-iodanyl acetate
Synonyms
(Diacetoxyiodo)benzene
Iodobenzene diacetate
(acetyloxy)(phenyl)-$l^{3}-iodanyl acetate
Iodobenzene I,I-diacetate
Iodosobenzene I,I-diacetate
(Diacetoxyiodo)benzene
(Diacetoxyiodo)benzene
DIB
Iodosobenzene diacetate
二乙酸亚碘酰苯
碘苯二乙酸酯
碘苯二乙酸
二乙酸亚碘酰苯
CAS Number
3240-34-4
EC Number
221-808-1
MDL Number
MFCD00008692
Beilstein Number
1879369
PubChem SID
162078139
24858980
24850764
PubChem CID
76724

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
H Acceptors H Donor
LogD (pH = 5.5) 2.1789038  LogD (pH = 7.4) 2.1789038 
Log P 2.1789038  Molar Refractivity 62.2473 cm3
Polarizability 25.908724 Å3 Polar Surface Area 52.6 Å2
Rotatable Bonds Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Melting Point
159-161°C expand Show data source
159-163°C expand Show data source
161-163 °C expand Show data source
161-163 °C(lit.) expand Show data source
Storage Warning
Irritant/Light Sensitive/Keep Cold expand Show data source
Light Sensitive expand Show data source
RTECS
DA3525000 expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
36/37/38 expand Show data source
Safety Statements
26-37 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Hazard statements
H315-H319-H335 expand Show data source
GHS Precautionary statements
P261-P305+P351+P338-P302+P352-P321-P405-P501A expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Purity
≥98.0% (AT) expand Show data source
96% expand Show data source
98% expand Show data source
98+% expand Show data source
Grade
purum expand Show data source
Linear Formula
C6H5I(O2CCH3)2 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - 178721 external link
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 external link
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

REFERENCES

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  • • 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).
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