[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
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) |
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
Abamectin manufacturer
JSK Chemicals
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