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HomeProduct name list[Bis(trifluoroacetoxy)iodo]benzene

[Bis(trifluoroacetoxy)iodo]benzene

Synonym(s):BTI;Iodobenzene I,I-bis(trifluoroacetate);PIFA

  • CAS NO.:2712-78-9
  • Empirical Formula: C10H5F6IO4
  • Molecular Weight: 430.04
  • MDL number: MFCD00009672
  • EINECS: 220-308-0
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-08-08 13:40:43
[Bis(trifluoroacetoxy)iodo]benzene Structural

What is [Bis(trifluoroacetoxy)iodo]benzene?

Chemical properties

White to pale yellow crystalline powder

The Uses of [Bis(trifluoroacetoxy)iodo]benzene

In oxidation, cyclization, dehydrogenation, and dearomatization reactions.

The Uses of [Bis(trifluoroacetoxy)iodo]benzene

[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.

What are the applications of Application

[Bis(trifluoroacetoxy)iodo]benzene is Reagent for Pummerer-like reactions, Chemoselective deprotection of dimethoxybenzyl ethers and more

Purification Methods

Crystallise the iodo compound from warm trifluoroacetic acid and dry it over NaOH pellets. Recrystallise it also from Me2CO/pet ether. Its melting point depends on the heating rate. [Spyroudis & Varvoglis Synthesis 445 1975, application: Almond et al. Org Synth 66 132 1988.]

Properties of [Bis(trifluoroacetoxy)iodo]benzene

Melting point: 121-125 °C(lit.)
storage temp.  Keep in dark place,Inert atmosphere,2-8°C
solubility  Chloroform (Slightly), Dichloromethane (Slightly), DMSO (Slightly)
form  Crystalline Powder
color  White to pale yellow
Water Solubility  insoluble
Sensitive  Moisture & Light Sensitive
BRN  764767
Stability: Air and Moisture Sensitive
CAS DataBase Reference 2712-78-9(CAS DataBase Reference)

Safety information for [Bis(trifluoroacetoxy)iodo]benzene

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P271:Use only outdoors or in a well-ventilated area.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for [Bis(trifluoroacetoxy)iodo]benzene

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