14353-88-9

Basic information

• Product Name: [BIS(TRIFLUOROACETOXY)IODO]PENTAFLUOROBENZENE
• Synonyms: [Bis(trifluoroacetoxy)iodo]pentafluorobenzene, Titr. 97%;FPIFA;PENTAFLUORO[BIS(TRIFLUOROACETOXY)IODO]BENZENE;IODOPENTAFLUOROBENZENE BIS(TRIFLUOROACETATE);[BIS(TRIFLUOROACETOXY)IODO]PENTAFLUOROBENZENE;[Bis(trifluoroacetoxy)]iodopentafluorobenzene 95%;[Bis(trifluoroacetoxy)]iodopentafluorobenzene95%
• CAS NO: 14353-88-9
• Molecular Formula: C₁₀F₁₁IO₄
• Molecular Weight: 519.99
• EINECS: 1533716-785-6
• Product Categories: Hypervalent Iodine Compounds;Oxidation;Synthetic Organic Chemistry
• Mol File: 14353-88-9.mol
• Article Data: 8

Chemical Properties

• Melting Point: 117-119 °C(lit.)
• Appearance: /
• Solubility: soluble in Methanol
• CAS DataBase Reference: [BIS(TRIFLUOROACETOXY)IODO]PENTAFLUOROBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: [BIS(TRIFLUOROACETOXY)IODO]PENTAFLUOROBENZENE(14353-88-9)
• EPA Substance Registry System: [BIS(TRIFLUOROACETOXY)IODO]PENTAFLUOROBENZENE(14353-88-9)

Safety Data

• Hazard Codes: C,Xi
• Statements: 34
• Safety Statements: 22-26-27-36/37/39-45
• RIDADR: UN 1759 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 14353-88-9(Hazardous Substances Data)

Usage

Description

[BIS(TRIFLUOROACETOXY)IODO]PENTAFLUOROBENZENE is a complex organic compound with a unique structure that features a benzene ring with pentafluoro substitution and an iodo group connected to two trifluoroacetoxy groups. It is known for its versatile reactivity and application in various chemical reactions.

Uses

Used in Chemical Synthesis:
[BIS(TRIFLUOROACETOXY)IODO]PENTAFLUOROBENZENE is used as a reactant or reagent for the following applications:
1. Oxidation of organic iodides using oxone and trifluoroacetic acid: It serves as an effective oxidizing agent, facilitating the conversion of organic iodides to the desired products.
2. Base hydrolysis: The compound can be used to promote hydrolysis reactions under basic conditions, leading to the formation of the corresponding products.
3. Oxidative cross-coupling of arenes: It acts as a coupling agent, enabling the formation of biaryl compounds through an oxidative process.
4. Oxidation of phenolic compounds with organohypervalent iodine: The compound is utilized to oxidize phenolic compounds, leading to the formation of various products with organohypervalent iodine.
5. Aziridination of alkenes: It is employed as a reagent in the aziridination process, where alkenes are converted to aziridines.
6. Oxidation of organic compounds: The compound is used to oxidize a wide range of organic compounds, promoting the formation of oxidized products.
7. Oxidative fragmentation of α-amino acids or β-amino alcohols: It is used to selectively oxidize and fragment α-amino acids or β-amino alcohols, leading to the formation of specific products.
8. Oxidative biaryl coupling of thiophenes: The compound is employed as a reagent in the oxidative coupling of thiophenes to form biaryl compounds.

InChI:InChI=1/C10F11IO4/c11-1-2(12)4(14)6(5(15)3(1)13)22(25-7(23)9(16,17)18)26-8(24)10(19,20)21

Upstream product

• 827-15-6 1,2,3,4,5-pentafluoro-6-iodobenzene 
• 407-25-0 trifluoroacetic anhydride 
• 359-48-8 trifluoroacetyl peroxide 
• 76-05-1 trifluoroacetic acid 
• 14353-90-3 1,2,3,4,5-pentafluoro-6-iodosylbenzene 
• 1109-15-5 tris(pentafluorophenyl)borate 

Downstream Products

• 14353-90-3 1,2,3,4,5-pentafluoro-6-iodosylbenzene 
• 383-63-1 ethyl trifluoroacetate, 
• 160001-85-4 1-(tert-butyl)-4-(trifluoromethyl)benzene 
• 2967-66-0 methyl 4-(trifluoromethyl)benzoate 
• 2557-13-3 3-trifluoromethylbenzoic acid methyl ester 
• 344-96-7 2-trifluoromethyl-benzoic acid methyl ester 
• 401-78-5 3-bromo-1-trifluoromethylbenzene 
• 392-83-6 o-trifluoromethylphenyl bromide 
• 402-43-7 p-trifluoromethylphenyl bromide 
• 368-77-4 3-trifluoromethylbenzonitrile 
• 455-18-5 4-CF₃C₆H₄CN 
• 447-60-9 2-(trifluoromethyl)benzonitrile 
• 709-63-7 1-(4-trifluoromethylphenyl)ethanone 
• 17408-14-9 1-(2-(trifluoromethyl)phenyl)ethan-1-one 

Relevant articles and documents

Simple direct synthesis of [bis(trifluoroacetoxy)iodo]arenes

A modified procedure for the direct synthesis of hypervalent [bis(trifluoroacetoxy)iodo]arenes is described. It avoids the use of hazardous reagents with the workup being only an aqueous extraction. Georg Thieme Verlag Stuttgart.

Alternative Strategies with Iodine: Fast Access to Previously Inaccessible Iodine(III) Compounds

Non-iodinated arenes can be easily and selectively converted into (diacetoxyiodo)arenes in a single step under mild conditions by using iodine triacetates as reagents. The oxidative step is decoupled from the synthesis of hypervalent iodine(III) reagents, which can now be prepared conveniently in a one-pot synthesis for subsequent reactions without prior purification. The chemistry of iodine triacetates was also expanded to heteroatom ligand exchanges to form novel inorganic hypervalent iodine compounds.

Facile One-Pot Synthesis of Diaryliodonium Salts from Arenes and Aryl Iodides with Oxone

A straightforward synthesis of diaryliodonium salts is achieved by using Oxone as the stoichiometric oxidant. Slow addition is the key to obtaining good yields and purities of the reaction products, which are highly useful reagents in many different areas of organic synthesis.

Fluorine-containing diaryliodonium salt and application thereof

The invention relates to fluorine-containing diaryliodonium salt as well as a preparation method and an application thereof. The fluorine-containing diaryliodonium salt has a structure represented as a formula I and is taken as an arylation reagent. The fluorine-containing diaryliodonium salt has the advantages that the preparation is easy, when the fluorine-containing diaryliodonium salt is applied to an arylation reaction, the arylation reaction condition is relatively mild, the selectivity of an arylation product is good and the like; in the formula I shown in the specification, R1 represents an aromatic ring group or a heteroaromatic ring group or represents a substituted aromatic ring group or a substituted heteroaromatic ring group, and Y represents a univalent organic or inorganic acid radical anion.