[Bis(trifluoroacetoxy)iodo]benzene

Base Information

• Chemical Name: [Bis(trifluoroacetoxy)iodo]benzene
• CAS No.: 2712-78-9
• Molecular Formula: C10H5F6IO4
• Molecular Weight: 430.042
• Hs Code.: 29036990
• European Community (EC) Number: 220-308-0
• UNII: 659SFV27XS
• DSSTox Substance ID: DTXSID40181584
• Nikkaji Number: J376.762K
• Wikipedia: (Bis(trifluoroacetoxy)iodo)benzene
• Wikidata: Q158535
• Mol file: 2712-78-9.mol

Synonyms:[Bis(trifluoroacetoxy)iodo]benzene;2712-78-9;(Bis(trifluoroacetoxy)iodo)benzene;PIFA;BIS(TRIFLUOROACETOXY)IODOBENZENE;Bis(I,I-trifluoroacetoxy)iodobenzene;Phenylbis(trifluoroacetato-O)iodine;Iodine, phenylbis(trifluoroacetato-O)-;UNII-659SFV27XS;bis-trifluoroacetoxyiodobenzene;659SFV27XS;iodobenzene bis(trifluoroacetate);phenyliodine bis(trifluoroacetate);EINECS 220-308-0;I,I-bis(trifluoroacetoxy)iodobenzene;phenyliodine(III) bis(trifluoroacetate);Iodine, phenylbis(trifluoroacetato-.kappa.O)-;[phenyl-(2,2,2-trifluoroacetyl)oxy-lambda3-iodanyl] 2,2,2-trifluoroacetate;iodine, phenylbis(trifluoroacetato)-;MFCD00009672;C10H5F6IO4;PhI(OCOCF3)2;SCHEMBL57095;bis(trifluoroacetoxy)iodo-benzene;DTXSID40181584;Bis(trifluoroacetoxy)phenyl iodine;[bis(trifluoroacetoxyl)iodo]benzene;[bis(trifluoro-acetoxy)iodo]benzene;[bis(trifluoroacetoxy) iodo]benzene;[bis(trifluoroacetoxy)-iodo]benzene;[bis(trifluoroacetoxy)iodo] benzene;[bis(trifluoroacetoxyl)-iodo]benzene;C10-H5-F6-I-O4;I,I-bis(trifluoroacetate)iodobenzene;Phenylbis(trifluoroacetato-?O)iodine;[bis-(trifluoroacetoxy) iodo]benzene;I,I-bis-(trifluoroacetoxy)iodobenzene;Iodobenzene I,I-bis(trifluoroacetate);AKOS005146009;AB00978;AC-3051;AM84863;CS-W011628;IODOBENZENE DI(TRIFLUOROACETATE);[Bis(trifluoroacetoxy)iodo]benzene, 97%;BIS(TRIFLUOROACETATO)PHENYL IODIDE;BTI;PHENYLIODOSO BIS(TRIFLUOROACETATE);AS-14346;BIS(TRIFLUOROACETATO)(PHENYL)IODINE;A5291;B1175;FT-0602447;BENZENE, (BIS(TRIFLUOROACETOXY)IODO)-;EN300-179189;I11501;Iodine, phenylbis[(2,2,2-trifluoroacetyl)oxy]-;PHENYLBIS(TRIFLUOROACETATO-.KAPPA.O)IODINE;Q158535;J-502779;Phenyl[bis(2,2,2-trifluoroacetoxy)]-lambda3-iodane;PHENYLIODINE(III) BIS(TRIFLUOROACETATE) [MI];PHENYLBIS(2,2,2-TRIFLUOROACETATO-.KAPPA.O)IODINE;[Bis(trifluoroacetoxy)iodo]benzene, purum, >=95.0% (AT);[phenyl-(2,2,2-trifluoroacetyl)oxy-3-iodanyl] 2,2,2-trifluoroacetate;phenyl[(2,2,2-trifluoroacetyl)oxy]-lambda3-iodanyl 2,2,2-trifluoroacetate

Chemical Property of [Bis(trifluoroacetoxy)iodo]benzene

Chemical Property:

• 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
• Storage Temp.: Keep Cold
• Sensitive.: Moisture & Light Sensitive
• Solubility.: Chloroform (Slightly), Dichloromethane (Slightly), DMSO (Slightly)
• Water Solubility.: insoluble
• XLogP3: 5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 5
• Exact Mass: 429.91368
• Heavy Atom Count: 21
• Complexity: 360

Purity/Quality:

99% ^*data from raw suppliers

[Bis(trifluoroacetoxy)iodo]benzene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)I(OC(=O)C(F)(F)F)OC(=O)C(F)(F)F
• 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.

Technology Process of [Bis(trifluoroacetoxy)iodo]benzene

There total 21 articles about [Bis(trifluoroacetoxy)iodo]benzene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

trimethylsilyl trifluoroacetate (400-53-3) + iodosylbenzene (536-80-1) → bis-[(trifluoroacetoxy)iodo]benzene (2712-78-9)

Guidance literature:

In dichloromethane; Ambient temperature;

Reference yield: 98.0%

[bis(acetoxy)iodo]benzene (3240-34-4) + trifluoroacetic acid (76-05-1) → bis-[(trifluoroacetoxy)iodo]benzene (2712-78-9)

Guidance literature:

at 20 ℃; for 1h;

Reference yield: 97.0%

iodobenzene (591-50-4) + trifluoroacetic acid (76-05-1) → bis-[(trifluoroacetoxy)iodo]benzene (2712-78-9)

Guidance literature:

With Oxone; In chloroform; at 20 ℃; for 1.2h;

DOI:10.1021/jo902733f

upstream raw materials:

[bis(acetoxy)iodo]benzene

trifluoroacetic acid

trimethylsilyl trifluoroacetate

iodosylbenzene

Downstream raw materials:

phenyl-λ³-iodanediyl dipropionate

di(chloroacetoxy)iodosobenzene

(dibenzoyloxyiodo)benzene

iodobenzene

Refernces

An intramolecular cyclization of phenol derivatives bearing aminoquinones using a hypervalent iodine reagent

10.1021/jo951439q

The research investigates the intramolecular cyclization of phenol derivatives bearing aminoquinones using a hypervalent iodine reagent, phenyliodine(III) bis(trifluoroacetate) (PIFA), with the aim of preparing novel antitumor compounds. The study selectively obtained azacarbocyclic spirodienone derivatives or phenol derivatives containing the 2,3-dihydro-1H-azepine systems by reacting ortho- or meta-substituted phenol derivatives with PIFA in 2,2,2-trifluoroethanol. The findings confirm the difference in reactivities between ortho- and meta-substituted phenol derivatives protected by methyl or silyl groups, allowing for the selective synthesis of pharmacologically important compounds.

A novel and direct synthesis of alkylated 2,2′-bithiophene derivatives using a combination of hypervalent iodine(III) reagent and BF₃·Et₂O

10.1039/b302462h

The research focuses on the development of a novel and direct synthetic method for alkylated 2,2'-bithiophene derivatives, which are significant precursors for oligo- and poly-thiophenes due to their valuable physical properties like electrical conductivity and electroluminescence. The study presents a nonmetallic oxidative coupling of alkylthiophene derivatives using a combination of hypervalent iodine(III) reagent, phenyliodine bis(trifluoroacetate) (PIFA), and boron trifluoride diethyl etherate (BF3·Et2O). The purpose of this research was to find a more direct and efficient route to bithiophenes without the need for transition metal catalyzed coupling reactions, which are typically required for their synthesis. The conclusions drawn from the study indicate that the PIFA-BF3·Et2O system successfully led to the formation of 2,2'-bithiophenes in moderate to good yields, providing a novel and direct route to these important compounds without the need for additional activation of thiophene monomers. This method offers a safer alternative to heavy metal reagents and addresses the challenge of selectively obtaining bithiophenes over polythiophenes, which is a common issue with conventional oxidative methods.

Divergent synthesis of lamellarin α 13-sulfate, 20-sulfate, and 13,20-disulfate

10.3987/COM-09-S(S)100

The study presents a divergent synthesis method for three sulfate derivatives of lamellarin, which are lamellarin 13-sulfate, 20-sulfate, and 13,20-disulfate. These compounds were synthesized using a common intermediate, where the 13-OH and 20-OH of the lamellarin core were differentially protected by MOM and benzyl groups. The synthesis involved a series of chemical reactions, including Suzuki-Miyaura coupling, selective debenzylation, trichloroethylsulfonation, reductive cleavage of the trichloroethyl ester, and others. Key chemicals used in the study include 3,4-dihydroxypyrrole bistriflate, arylboronic acids, MOM-Cl, NBS, tert-BuLi, trimethyl borate, Pd(PPh3)4, Cu2O, quinoline, phenyliodine bis(trifluoroacetate) (PIFA), BF3·OEt2, DDQ, and various solvents and reagents for protection and deprotection steps. These chemicals served to construct the lamellarin core, introduce the sulfate groups selectively, and carry out the necessary transformations to obtain the desired sulfate derivatives. The purpose of these chemicals was to facilitate the synthesis of the lamellarin derivatives, which are of interest due to their unique structures and potential biological activities, particularly as anti-HIV agents.

Metal-Free-Visible Light C-H Alkylation of Heteroaromatics via Hypervalent Iodine-Promoted Decarboxylation

10.1021/acs.orglett.8b01085

The study presents a metal-free photoredox C?H alkylation of heteroaromatics using hypervalent iodine dicarboxylates and an organic photocatalyst, 9-mesityl-10-methyl acridinium (MesAcr), under blue LED light. The method leverages readily available carboxylic acids as coupling partners and operates under mild conditions at room temperature. Key chemicals include bis(trifluoroacetoxy)iodobenzene (PIFA) as the oxidant, which helps avoid complications from forming undesired alkylated products and eliminates the need for additional trifluoroacetic acid. The study explores the scope of various carboxylic acids, which generate different alkyl radicals (primary, secondary, tertiary) under the reaction conditions, and tests a range of heteroaromatics and complex molecules, including drugs like voriconazole, varenicline, and quinine, demonstrating good functional group tolerance. Mechanistic investigations, including control experiments, photophysical studies, and DFT calculations, suggest a distinct reaction mechanism involving a chain reaction with a low quantum yield, likely due to an inefficient initiation step.