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
Beilstein:
764767
EC Number:
MDL number:
UNSPSC Code:
12352002
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
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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Related Categories
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.
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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
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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Customers Also Viewed
Tetrahedron Letters, 35, 2541-2541 (1994)
Tetrahedron Letters, 33, 6065-6065 (1992)
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
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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