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[Bis(trifluoroacetoxy)iodo]benzene, 97%, Thermo Scientific Chemicals

Catalog No. AAL1514114
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[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

25 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

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
SDS

RUO – Research Use Only

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