[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

InChI

InChI=1S/C10H5F6IO4/c11-9(12,13)7(18)20-17(6-4-2-1-3-5-6)21-8(19)10(14,15)16/h1-5H

InChIKey

PEZNEXFPRSOYPL-UHFFFAOYSA-N

SMILES

I(C1C=CC=CC=1)(OC(=O)C(F)(F)F)OC(=O)C(F)(F)F

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

Synthesis

Under an argon atmosphere (protected with an argon balloon), iodobenzene (28 mL, 250 mmol) was added to the reaction vessel, followed by trifluoroacetic acid (TFA, 100 mL) and chloroform (CHCl3, 240 mL). Oxone (116 g, 377 mmol, 1.5 eq.) was added slowly under vigorous stirring conditions. Immediately after the addition, the reaction mixture was cooled in an ice bath for 30 min due to the exothermic nature of the reaction. After removal of the ice bath, the reaction mixture was stirred continuously at room temperature for 48 hours. Upon completion of the reaction, the solid was suspended in chloroform and separated by filtration. The filtrate was concentrated to dryness under reduced pressure to afford [bis(trifluoroacetoxy)iodo]benzene as an off-white solid (89.3 g, 208 mmol, 83% yield). The product was characterized by 1H NMR (300 MHz, chloroform-d): δ 8.20 (d, J = 7.8 Hz, 2H), 7.74 (t, J = 7.4 Hz, 1H), 7.62 (t, J = 7.8 Hz, 2H).

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.]

References

[1] Journal of Organic Chemistry, 2010, vol. 75, # 6, p. 2119 - 2122
[2] Patent: WO2018/106112, 2018, A1. Location in patent: Page/Page column 67
[3] Bulletin of the Chemical Society of Japan, 2006, vol. 79, # 1, p. 142 - 144
[4] Nature Chemistry, 2018, vol. 10, # 2, p. 200 - 204
[5] Russian Journal of General Chemistry, 1994, vol. 64, # 12.2, p. 1826

[Bis(trifluoroacetoxy)iodo]benzene(2712-78-9)Related Product Information

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