232130
[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:
Molecular Weight:
430.04
UNSPSC Code:
12352002
NACRES:
NA.22
PubChem Substance ID:
EC Number:
220-308-0
Beilstein/REAXYS Number:
764767
MDL number:
Assay:
97%
Form:
solid
Quality Level
assay
97%
form
solid
reaction suitability
reagent type: oxidant
mp
121-125 °C (lit.)
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
Application
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.
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.
Reactant or reagent for:
- Pummerer-like reactions
- Chemoselective deprotection of dimethoxybenzyl ethers
- Mediating oxidative cycloisomerization
- Tosyloxylation of anilides
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signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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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, 35, 2541-2541 (1994)
Tetrahedron Letters, 33, 6065-6065 (1992)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 232130-50G | 04061838783370 |
| 232130-10G | 04061838783363 |