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Merck
CN

15230

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

Key Documents

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grade

purum

Quality Level

200

Assay

≥95.0% (AT)

form

solid

reaction suitability

reagent type: oxidant

mp

121-125 °C (lit.)
122-125 °C

functional group

fluoro
iodo

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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN3139
BCCB0155

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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)
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
A. Varvoglis
Synthesis, 709-709 (1984)
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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