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  8. [Bis(trifluoroacetoxy)iodo]benzene, 97%

[Bis(trifluoroacetoxy)iodo]benzene, 97%

Catalog No. AAL1514106
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Quantity:
25 g
5 g
Catalog No. Quantity
AAL1514106 5 g
AAL1514114 25 g
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Catalog No. AAL1514106

Supplier: Thermo Scientific Chemicals L1514106

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Description

CAS: 2712-78-9 | C10H5F6IO4 | 430.041 g/mol

[Bis(trifluoroacetoxy)iodo]benzene acts as a reagent in Pummerer-like reactions. It plays an important role in the direct alfa-hydroxylation of ketones under acidic conditions. It is involved in the cyclization of styryl amines to N-alkyl or N-aryl indoles. It serves as a reagent for the chemoselective deprotection of dimethoxybenzyl ethers and tosyloxylation of anilides. Further, it is used in the synthesis of 1,3,4-oxadiazoles by the oxidation of N-acylhydrazones. In addition to this, it is employed in the Hofmann rearrangement for the conversion of cyclobutanecarboxamide to cyclobutylamine hydrochloride.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications
[Bis(trifluoroacetoxy)iodo]benzene acts as a reagent in Pummerer-like reactions. It plays an important role in the direct alfa-hydroxylation of ketones under acidic conditions. It is involved in the cyclization of styryl amines to N-alkyl or N-aryl indoles. It serves as a reagent for the chemoselective deprotection of dimethoxybenzyl ethers and tosyloxylation of anilides. Further, it is used in the synthesis of 1,3,4-oxadiazoles by the oxidation of N-acylhydrazones. In addition to this, it is employed in the Hofmann rearrangement for the conversion of cyclobutanecarboxamide to cyclobutylamine hydrochloride.

Solubility
Insoluble in water.

Notes
Light and moisture sensitive. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with strong bases.

Chemical Identifiers

CAS 2712-78-9
Molecular Formula C10H5F6IO4
Molecular Weight (g/mol) 430.041
MDL Number MFCD00009672
InChI Key PEZNEXFPRSOYPL-UHFFFAOYSA-N
Synonym bis trifluoroacetoxy iodo benzene, pifa, unii-659sfv27xs, bis-trifluoroacetoxyiodobenzene, phenylbis trifluoroacetato-o iodine, bis i,i-trifluoroacetoxy iodobenzene, iodine, phenylbis trifluoroacetato-o, bis trifluoracetoxy-iodobenzene, bis trifluoroacetoxy phenyl iodane
PubChem CID 102317
IUPAC Name [phenyl-(2,2,2-trifluoroacetyl)oxy-$l^{3}-iodanyl] 2,2,2-trifluoroacetate
SMILES C1=CC=C(C=C1)I(OC(=O)C(F)(F)F)OC(=O)C(F)(F)F

Specifications

Melting Point 122°C to 125°C
Quantity 5 g
Beilstein 764767
Sensitivity Light and moisture sensitive
Solubility Information Insoluble in water.
Formula Weight 430.04
Percent Purity 97%
Chemical Name or Material [Bis(trifluoroacetoxy)iodo]benzene

Safety and Handling

Hazard Category H315-H319-H335
Hazard Statement GHS H Statement
H315-H319-H335
Causes skin irritation.
Causes serious eye irritation.
May cause respiratory irritation.
Precautionary Statement P261-P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P362-P501c
EINECSNumber 220-308-0
TSCA No
Recommended Storage Keep cold

RUO – Research Use Only