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[Bis(trifluoroacetoxy)iodo]benzene

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[Bis(trifluoroacetoxy)iodo]benzene Basic information

Product Name:
[Bis(trifluoroacetoxy)iodo]benzene
Synonyms:
  • IODOSOBENZENE I,I-BIS(TRIFLUOROACETATE)
  • IODINE, PHENYLBIS(TRIFLUOROACETATO)-
  • IODOBENZENE BIS(TRIFLUOROACETATE)
  • IODOBENZENE I,I-BIS(TRIFLUOROACETATE)
  • BTI
  • BIS(TRIFLUORACETOXY)- IODOBENZENE
  • [BIS(TRIFLUOROACETOXY)IODO]BENZENE
  • [Bis(trifluoroacetoxy)](phenyl)iodane
CAS:
2712-78-9
MF:
C10H5F6IO4
MW:
430.04
EINECS:
220-308-0
Product Categories:
  • Carbazoles
Mol File:
2712-78-9.mol
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[Bis(trifluoroacetoxy)iodo]benzene Chemical Properties

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)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36-37/39
WGK Germany 
3
4.10-8-9-21
Hazard Note 
Irritant/Keep Cold
HazardClass 
IRRITANT, KEEP COLD, LIGHT SENSITIVE
HS Code 
29036990

MSDS

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[Bis(trifluoroacetoxy)iodo]benzene Usage And Synthesis

Chemical Properties

White to pale yellow crystalline powder

Uses

[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.

Uses

In oxidation, cyclization, dehydrogenation, and dearomatization reactions.

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.]

[Bis(trifluoroacetoxy)iodo]benzene Preparation Products And Raw materials

Raw materials

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