phenyl[(trifluoroacetyl)oxy]-$l^{3}-iodanyl 2,2,2-trifluoroacetate

• ChemBase ID: 8596
• Molecular Formular: C10H5F6IO4
• Molecular Mass: 430.0391892
• Monoisotopic Mass: 429.91367596
• SMILES: O=C(C(F)(F)F)O[I](c1ccccc1)OC(=O)C(F)(F)F
• Canonical SMILES: O=C(C(F)(F)F)O[I](c1ccccc1)OC(=O)C(F)(F)F
• InChI: InChI=1S/C10H5F6IO4/c11-9(12,13)7(18)20-17(6-4-2-1-3-5-6)21-8(19)10(14,15)16/h1-5H
• InChIKey: PEZNEXFPRSOYPL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: phenyl[(trifluoroacetyl)oxy]-$l^{3}-iodanyl 2,2,2-trifluoroacetate; phenyl[(trifluoroacetyl)oxy]-λ^3-iodanyl 2,2,2-trifluoroacetate
• IUPAC Traditional name: phenyl[(trifluoroacetyl)oxy]-$l^{3}-iodanyl 2,2,2-trifluoroacetate; phenyl[(trifluoroacetyl)oxy]-λ^3-iodanyl 2,2,2-trifluoroacetate
• Synonyms: [Bis(trifluoroacetoxy)iodo]benzene; [Bis(trifluoroacetoxy)iodo]benzene; [Bis(trifluoroacetoxy)](phenyl)iodane; Iodosobenzene bis(trifluoroacetate); BTI; PIFA; Iodobenzene I,I-bis(trifluoroacetate); [Bis(trifluoroacetoxy)iodo]benzene; (Bis(trifluoroacetoxy)iodo)benzene; 二(三氟乙酰氧基)碘代苯; I,I-双(三氟乙酸)碘苯; [双(三氟乙酰氧基)碘]苯

Database IDs

• CAS Number: 2712-78-9
• EC Number: 220-308-0
• MDL Number: MFCD00009672
• Beilstein Number: 764767
• PubChem SID: 24849220; 160971903; 24853882
• PubChem CID: 102317
• Chemspider ID: 92428
• Wikipedia Title: (Bis(trifluoroacetoxy)iodo)benzene

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 5.005431
• LogD (pH = 7.4): 5.005431
• Log P: 5.005431
• Molar Refractivity: 64.8731 cm^3
• Polarizability: 25.709503 Å^3
• Polar Surface Area: 52.6 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 121-125 °C(lit.); 122-125 °C; 122-125°C; 122-125°C

Safety Information

• Storage Warning: IRRITANT, KEEP COLD, LIGHT SENSITIVE; Irritant/Light Sensitive/Moisture Sensitive/Keep Cold/Store under Argon; Moisture & Light Sensitive
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥95.0% (AT); 97%
• Grade: purum
• Linear Formula: (CF3CO2)2IC6H5

DETAILS

Apollo Scientific Ltd - PC0403

Used to estimate asparagine and glutamine in peptides and proteins.

Sigma Aldrich - 232130

Packaging
10, 50 g in glass bottle
Application
Reactant or reagent for:
• Pummerer-like reactions1,2
• Chemoselective deprotection of dimethoxybenzyl ethers3
• Mediating oxidative cycloisomerization4,5
• Tosyloxylation of anilides6
Used for the direct α-hydroxylation of ketones under acidic conditions. Also employed as a p-fluorination reagent of 4-alkylphenols in the presence of HF·pyridine (cat. no. 184225) for synthesis of 4-fluorocyclohexa-2,5-dienones.Reagent for the oxidation of N-acylhydrazones to 1,3,4-oxadiazoles. Promotes the cyclization of styryl amines to N-alkyl or N-aryl indoles.

Sigma Aldrich - 15230

Other Notes
Reagent for dehydrogenation and oxidation reactions, review7; New reagent for the direct conversions of amides to amines (Hofmann-type rearrangement) and key substance for carboxyterminal peptide sequencing8; Smooth dethioacetalization to the carbonyls9
Application
Reactant or reagent for:
• Pummerer-like reactions1,2
• Chemoselective deprotection of dimethoxybenzyl ethers3
• Mediating oxidative cycloisomerization4,5
• Tosyloxylation of anilides6

REFERENCES

• Terminal alkynes are oxidized by PIFA to ɑ-hydroxy ketones: Tetrahedron Lett., 26, 3837 (1985).
• 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).
• 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).
• Mediates the selective cyanation of electron-rich aromatics with Trimethylsilyl cyanide, A19598, e.g. indoles to 2-cyanoindoles: Org. Lett., 7, 537 (2005).
• 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).