[Bis(trifluoroacetoxy)iodo]benzene, 97%
[Bis(trifluoroacetoxy)iodo]benzene, 97%
[Bis(trifluoroacetoxy)iodo]benzene, 97%
Thermo Scientific Chemicals

[Bis(trifluoroacetoxy)iodo]benzene, 97%

CAS: 2712-78-9 | C10H5F6IO4 | 430.041 g/mol
Have Questions?
Change viewbuttonViewtableView
Quantity:
5 g
25 g
Catalog number L15141.06
also known as L15141-06
Price (USD)
43.65
Online Exclusive
48.10
Save 4.45 (9%)
Each
Quantity:
5 g
Request bulk or custom format
Price (USD)
43.65
Online Exclusive
48.10
Save 4.45 (9%)
Each
Chemical Identifiers
CAS2712-78-9
IUPAC Namephenyl[(2,2,2-trifluoroacetyl)oxy]-λ³-iodanyl 2,2,2-trifluoroacetate
Molecular FormulaC10H5F6IO4
InChI KeyPEZNEXFPRSOYPL-UHFFFAOYSA-N
SMILESFC(F)(F)C(=O)O[I](OC(=O)C(F)(F)F)C1=CC=CC=C1
View more
SpecificationsSpecification SheetSpecification Sheet
FormCrystals or powder or crystalline powder
Identification (FTIR)Conforms
Assay (Iodometric Titration)≥96.0 to ≤104.0%
Melting Point (clear melt)119.0-128.0?C
Appearance (Color)White
[Bis(trifluoroacetoxy)iodo]benzene acts as a reagent in Pummerer-like reactions. It plays an important role in the direct alfa-hydroxylation of ketones under acidic conditions. It is involved in the cyclization of styryl amines to N-alkyl or N-aryl indoles. It serves as a reagent for the chemoselective deprotection of dimethoxybenzyl ethers and tosyloxylation of anilides. Further, it is used in the synthesis of 1,3,4-oxadiazoles by the oxidation of N-acylhydrazones. In addition to this, it is employed in the Hofmann rearrangement for the conversion of cyclobutanecarboxamide to cyclobutylamine hydrochloride.

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
[Bis(trifluoroacetoxy)iodo]benzene acts as a reagent in Pummerer-like reactions. It plays an important role in the direct alfa-hydroxylation of ketones under acidic conditions. It is involved in the cyclization of styryl amines to N-alkyl or N-aryl indoles. It serves as a reagent for the chemoselective deprotection of dimethoxybenzyl ethers and tosyloxylation of anilides. Further, it is used in the synthesis of 1,3,4-oxadiazoles by the oxidation of N-acylhydrazones. In addition to this, it is employed in the Hofmann rearrangement for the conversion of cyclobutanecarboxamide to cyclobutylamine hydrochloride.

Solubility
Insoluble in water.

Notes
Light and moisture sensitive. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with strong bases.
RUO – Research Use Only

General References:

  1. Hypervalent iodine oxidizing agent, cf Iodosobenzene diacetate, B24531. PIFA oxidizes hydroquinones and catechols to benzoquinones. In the presence of a nucleophile, 4-substituted phenols give the corresponding 4,4-disubstituted cyclohexadienone: J. Chem. Soc., Perkin 1, 1891 (1993); 2047 (1994), and refs. therein. In water, 1,4-dimethoxy aromatics undergo oxidative demethylation to p-quinones: Tetrahedron Lett., 42, 6899 (2001). In TFA, acetanilides can be hydroxylated in the p-position: J. Org. Chem., 67, 7424 (2002).
  2. Terminal alkynes are oxidized by PIFA to ɑ-hydroxy ketones: Tetrahedron Lett., 26, 3837 (1985).
  3. Primary amides undergo a Hofmann-like rearrangement to amines, avoiding the harsh conditions often required for the classical method: J. Org. Chem., 49, 4272, 4277 (1984); Synth. Commun., 18, 1615 (1988); Org. Synth. Coll., 8, 132 (1993). Promotes the azidation of alkyl groups of p-alkylanisoles with TMS azide: Tetrahedron Lett., 32, 4321 (1991); J. Am. Chem. Soc., 116, 3684 (1994); Synlett, 427 (1994), and also the direct nucleophilic sulfenylation and thiocyanation of phenol ethers with thiols and TMS isothiocyanate respectively: Synlett, 211 (1995); J. Org. Chem., 60, 7144 (1995).
  4. Mediates the selective cyanation of electron-rich aromatics with Trimethyl silyl cyanide, A19598, e.g. indoles to 2-cyanoindoles: Org. Lett., 7, 537 (2005).
  5. For a brief feature on uses of this reagent in synthesis, see: Synlett, 2851 (2006). For a comprehensive review of polyvalent iodine compounds, see: Chem. Rev., 96, 1123 (1996).