[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
• Uses: In oxidation, cyclization, dehydrogenation, and dearomatization reactions. [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.

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:

iodobenzene

benzyl chloride

benzenetellurinyl trifluoroacetate

isopropyl Trifluoroacetate

Refernces

• 1、 Carreras, Virginie,Sandtorv, Alexander H.,Stuart, David R.. "Synthesis of Aryl(2,4,6-trimethoxyphenyl)iodonium Trifluoroacetate Salts". . p. 1279 - 1284. Retrieved 2017.
• 2、 Szantay, Csaba,Blasko, Gabor,Barczai-Beke, Marietta,Pechy, Peter,Dornyei, Gabor. "STUDIES AIMING AT THE SYNTHESIS OF MORPHINE II. Studies on Phenolic Coupling of N-Norreticuline Derivates". . p. 3509 - 3512. Retrieved 1980.
• 3、 Alcock,Waddington. "-". . p. 4103,4107. Retrieved 1963.
• 4、 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.. "Ligand exchange of aryl iodine dicarboxylates to form reagents with differing solubilities". . p. 79 - 85. Retrieved 2021/05/11.
• 5、 Doiuchi, Daiki,Uchida, Tatsuya. "Catalytic Highly Regioselective C-H Oxygenation Using Water as the Oxygen Source: Preparation of 17O/18O-Isotope-Labeled Compounds". supporting information. p. 7301 - 7305. Retrieved 2021/10/01.