What is the [Bis(trifluoroacetoxy)iodo]benzene?

[Bis(trifluoroacetoxy)iodo]benzene is White to pale yellow crystalline powder, while it's Molecular Formula is C10H5F6IO4. White to pale yellow crystalline powder [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 is the CAS number for [Bis(trifluoroacetoxy)iodo]benzene?

The CAS number of [Bis(trifluoroacetoxy)iodo]benzene is 2712-78-9.

What is [Bis(trifluoroacetoxy)iodo]benzene (2712-78-9) used for?

[Bis(trifluoroacetoxy)iodo]benzene is a white to pale yellow crystalline powder that is widely utilized in various chemical reactions due to its unique properties. It is known for its ability to act as a reagent in a range of processes, including oxidation, cyclization, dehydrogenation, and dearomatization reactions.InChI:InChI=1/C10H3F6IO4/c11-9(12,13)7(18)20-5-3-1-2-4(17)6(5)21-8(19)10(14,15)16/h1-3H

What is the [Bis(trifluoroacetoxy)iodo]benzene?

[Bis(trifluoroacetoxy)iodo]benzene is White to pale yellow crystalline powder, while it's Molecular Formula is C10H5F6IO4. White to pale yellow crystalline powder [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 is the CAS number for [Bis(trifluoroacetoxy)iodo]benzene?

The CAS number of [Bis(trifluoroacetoxy)iodo]benzene is 2712-78-9.

What is [Bis(trifluoroacetoxy)iodo]benzene (2712-78-9) used for?

[Bis(trifluoroacetoxy)iodo]benzene is a white to pale yellow crystalline powder that is widely utilized in various chemical reactions due to its unique properties. It is known for its ability to act as a reagent in a range of processes, including oxidation, cyclization, dehydrogenation, and dearomatization reactions.InChI:InChI=1/C10H3F6IO4/c11-9(12,13)7(18)20-5-3-1-2-4(17)6(5)21-8(19)10(14,15)16/h1-3H

Product classification

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[Bis(trifluoroacetoxy)iodo]benzene

Product Name: [Bis(trifluoroacetoxy)iodo]benzene
CAS: 2712-78-9
Purity:
Appearance: White to pale yellow crystalline powder

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Product Details

Factory Supply industrial standard [Bis(trifluoroacetoxy)iodo]benzene 2712-78-9 In Stock

Molecular Formula:C10H5F6IO4
Molecular Weight:430.042
Appearance/Colour:White to pale yellow crystalline powder
Vapor Pressure:0.008mmHg at 25°C
Melting Point:121-125 °C(lit.)
Refractive Index:1.483
Boiling Point:267.573oC at 760 mmHg
Flash Point:115.624oC
PSA：52.60000
Density:1.95g/cm3
LogP:3.40360

[Bis(trifluoroacetoxy)iodo]benzene(Cas 2712-78-9) Usage

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.]

General Description

[Bis(trifluoroacetoxy)iodo]benzene (PIFA) is a hypervalent iodine(III) reagent widely used in organic synthesis for oxidative transformations, including intramolecular cyclizations, oxidative couplings, and decarboxylative alkylations. It serves as a versatile oxidant under mild conditions, enabling selective reactions such as the formation of azacarbocyclic spirodienones, oxidative dimerization of thiophenes, and metal-free C–H functionalizations. Its reactivity is often enhanced by additives like BF3·Et2O or photocatalysts, facilitating efficient bond formations without heavy metals. PIFA is particularly valued for its ability to generate radical intermediates and its compatibility with complex substrates, making it useful in pharmaceutical and materials chemistry.

InChI:InChI=1/C10H3F6IO4/c11-9(12,13)7(18)20-5-3-1-2-4(17)6(5)21-8(19)10(14,15)16/h1-3H

2712-78-9 Relevant articles

SECONDARY BONDING. PART 13. ARYL-TELLURIUM(IV) AND -IODINE(III) ACETATES AND TRIFLUOROACETATES. THE CRYSTAL AND MOLECULAR STRUCTURES OF BIS-(p-METHOXYPHENYL)TELLURIUM DIACETATE, μ-OXO-BIS HYDRATE, AND BENZENE

Alcock, Nathaniel W.,Harrison, W. David,Howes, Colin

, p. 1709 - 1716 (1984)

The crystal and molecular structures of ...

Synthesis of Aryl(2,4,6-trimethoxyphenyl)iodonium Trifluoroacetate Salts

Carreras, Virginie,Sandtorv, Alexander H.,Stuart, David R.

, p. 1279 - 1284 (2017)

The direct synthesis of aryl(2,4,6-trime...

Easy preparation of [bis(trifluoroacetoxy)iodo]arenes from iodoarenes, with sodium percarbonate as the oxidant

Kazmierczak, Pawel,Skulski, Lech

, p. 810 - 812 (2002)

Easy and effective preparations of the n...

STUDIES AIMING AT THE SYNTHESIS OF MORPHINE II. Studies on Phenolic Coupling of N-Norreticuline Derivates

Szantay, Csaba,Blasko, Gabor,Barczai-Beke, Marietta,Pechy, Peter,Dornyei, Gabor

, p. 3509 - 3512 (1980)

The synthesis of salutaridine derivative...

-

Parham,Loudon

, p. 1 (1978)

-

Alcock,Waddington

, p. 4103,4107 (1963)

Direct and convenient synthesis of [bis(trifluoroacetoxy)iodo]arenes from iodoarenes

Hossain, Delwar,Kitamura, Tsugio

, p. 142 - 144 (2006)

An easy, safe, and effective method for ...

Ligand exchange of aryl iodine dicarboxylates to form reagents with differing solubilities

Seecharan, Vanie,Armand, Lyse,Noorollah, Jennifer,Singh, Nirvanie,Zhang, Andrew,Freddo, Kevin P.,Spatola, Nicholas,Prasad, Sailesh,Chaudhry, Azka,War, Su Wint,Hyatt, I.F. Dempsey,Silverio, Daniel L.

, p. 79 - 85 (2021/05/11)

Hypervalent iodine (HVI) reagents are em...

Catalytic Highly Regioselective C-H Oxygenation Using Water as the Oxygen Source: Preparation of 17O/18O-Isotope-Labeled Compounds

Doiuchi, Daiki,Uchida, Tatsuya

supporting information, p. 7301 - 7305 (2021/10/01)

We found that the oxygen atom of water i...

Chemoselective Cleavage of Si-C(sp3) Bonds in Unactivated Tetraalkylsilanes Using Iodine Tris(trifluoroacetate)

Matsuoka, Keitaro,Komami, Narumi,Kojima, Masahiro,Mita, Tsuyoshi,Suzuki, Kimichi,Maeda, Satoshi,Yoshino, Tatsuhiko,Matsunaga, Shigeki

supporting information, p. 103 - 108 (2021/01/13)

Organosilanes are synthetically useful r...

Direct C-H α-Arylation of Enones with ArI(O2CR)2 Reagents

Sousa E Silva, Felipe Cesar,Van, Nguyen T.,Wengryniuk, Sarah E.

supporting information, p. 64 - 69 (2020/01/22)

α-Arylation of α,β-unsaturated ketones c...

2712-78-9 Process route

: 591-50-4
iodobenzene

: 407-25-0
trifluoroacetic anhydride

: 636-98-6
p-nitrobenzene iodide

: 118311-30-1
μ-oxo

: 2712-78-9
bis-[(trifluoroacetoxy)iodo]benzene

Conditions

Conditions	Yield
With nitric acid; acetic anhydride; In dichloromethane; at -20 ℃; for 0.666667h;	2.5% 2 g
With nitric acid; acetic anhydride; In dichloromethane; at -20 ℃; for 0.666667h; Product distribution; variation of temperature, reagent, time;	2.5% 2 g

: 591-50-4
iodobenzene

: 14353-88-9
iodopentafluorobenzene bis(trifluoroacetate)

: 827-15-6
1,2,3,4,5-pentafluoro-6-iodobenzene

: 2712-78-9
bis-[(trifluoroacetoxy)iodo]benzene