[Bis(trifluoroacetoxy)iodo]benzene, 97%

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.

Specifications

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

• 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

SDS

RUO – Research Use Only