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15230

Sigma-Aldrich

[Bis(trifluoroacetoxy)iodo]benzene

purum, ≥95.0% (AT)

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/REAXYS Number:
764767
EC Number:
220-308-0
MDL number:
MFCD00009672
UNSPSC Code:
12352002
PubChem Substance ID:
329750783
NACRES:
NA.22

grade

purum

Quality Level

200

assay

≥95.0% (AT)

form

solid

reaction suitability

reagent type: oxidant

mp

121-125 °C (lit.)
122-125 °C

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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Related Categories

Application

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

Other Notes

Reagent for dehydrogenation and oxidation reactions, review; New reagent for the direct conversions of amides to amines (Hofmann-type rearrangement) and key substance for carboxyterminal peptide sequencing; Smooth dethioacetalization to the carbonyls

Pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCB0155
BCBP3064V
BCBH3170V
BCBD2462V
BCBC8019V

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M.R. Almond et al.
Organic Syntheses, 66, 132-132 (1988)
G. Stork et al.
Tetrahedron Letters, 30, 287-287 (1989)
A. Varvoglis
Synthesis, 709-709 (1984)
William C Skarnes et al.
Methods (San Diego, Calif.), 164-165, 18-28 (2019-06-20)
The generation of induced pluripotent stem cell models of human disease requires efficient modification of one or both alleles depending on dominant or recessive inheritance of the disease. To faithfully recapitulate many disease variants, the introduction of a single base
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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