[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)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

F 

4.10-8-9-21

Hazard Note 

Irritant/Keep Cold

HazardClass 

IRRITANT, KEEP COLD, LIGHT SENSITIVE

HS Code 

29036990

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

[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.

reaction suitability

reagent type: oxidant

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(2712-78-9)Related Product Information

• (Trifluoromethoxy)benzene
• Iodine
• Ethylbenzene
• Anisole
• Allylbenzene
• Sodium triacetoxyborohydride
• (Diacetoxyiodo)benzene
• Acetoxyacetic acid
• Benzene
• Acetoxyacetyl chloride
• Povidone iodine
• 2-Phenoxyethanol
• Sliver bis(trifluoromethane sulfonimide)
• Cobalt bis(trifluoroMethylsulfonyl)iMide
• Silicon tetraacetate
• BIS(DICYCLOHEXYLPHOSPHINO)METHANE
• Bis(dibenzylideneacetone)palladium
• Bis(2-dicyclohexylphosphinophenyl)ether, 98%