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Sigma-Aldrich

[Bis(trifluoroacetoxy)iodo]benzene

97%

Synonym(s):

BTI, Iodobenzene I,I-bis(trifluoroacetate), PIFA

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About This Item

Linear Formula:
(CF3CO2)2IC6H5
CAS Number:
2712-78-9
Molecular Weight:
430.04
Beilstein:
764767
EC Number:
220-308-0
MDL number:
MFCD00009672
UNSPSC Code:
12352002
PubChem Substance ID:
24853882
NACRES:
NA.22

Quality Level

200

Assay

97%

form

solid

reaction suitability

reagent type: oxidant

mp

121-125 °C (lit.)

SMILES string

FC(F)(F)C(=O)O[I](OC(=O)C(F)(F)F)c1ccccc1

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

InChI key

PEZNEXFPRSOYPL-UHFFFAOYSA-N

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Application

Reactant or reagent for:
  • Pummerer-like reactions
  • Chemoselective deprotection of dimethoxybenzyl ethers
  • Mediating oxidative cycloisomerization
  • Tosyloxylation of anilides
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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Yunfei Du et al.
Organic letters, 8(26), 5919-5922 (2006-12-15)
[Structure: see text] A variety of N-arylated and N-alkylated indole derivatives were synthesized by way of a phenyliodine bis(trifluoroacetate) (PIFA)-mediated intramolecular cyclization. This novel method allows for the construction of an indole skeleton by joining the N-atom on the side
Tetrahedron Letters, 33, 6065-6065 (1992)
Tetrahedron Letters, 35, 2541-2541 (1994)
Synthetic Communications, 36, 2927-2927 (2006)
Determination of asparagine and glutamine in polypeptides using bis(I,I-trifluoroacetoxy)iodobenzene.
L M Soby et al.
Analytical biochemistry, 113(1), 149-153 (1981-05-01)
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