129112-26-1

Basic information

• Product Name: 2-IODOPHENYL TRIFLUOROMETHANESULFONATE
• Synonyms: 2-IODOPHENYL TRIFLUOROMETHANESULFONATE;2-IODOPHENYL TRIFLUOROMETHANESULFONATE, 97% MIN.;2-Iodophenyl triflate;Trifluoromethanesulfonic Acid 2-Iodophenyl Ester 2-Iodophenyl Triflate
• CAS NO: 129112-26-1
• Molecular Formula: C₇H₄F₃IO₃S
• Molecular Weight: 352.07
• Mol File: 129112-26-1.mol

Chemical Properties

• Boiling Point: 308℃
• Flash Point: 140℃
• Appearance: /
• Density: 2.035
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.5100 to 1.5150
• CAS DataBase Reference: 2-IODOPHENYL TRIFLUOROMETHANESULFONATE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-IODOPHENYL TRIFLUOROMETHANESULFONATE(129112-26-1)
• EPA Substance Registry System: 2-IODOPHENYL TRIFLUOROMETHANESULFONATE(129112-26-1)

Safety Data

• Hazardous Substances Data: 129112-26-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2-IODOPHENYL TRIFLUOROMETHANESULFONATE is used as a reagent for the conversion of alcohols to iodides, which is crucial in the synthesis of various organic compounds. Its application reason lies in its ability to facilitate this transformation under mild conditions with high selectivity, making it a preferred choice in organic chemistry.
Used in the Preparation of Aryl Iodides:
In the field of synthetic chemistry, 2-IODOPHENYL TRIFLUOROMETHANESULFONATE is used as a reagent for the preparation of aryl iodides from aryl boronic acids. The reason for its use in this application is its effectiveness in promoting the conversion process, providing a pathway to access aryl iodides, which are important intermediates in the synthesis of pharmaceuticals and other organic compounds.
Used in Research Laboratories:
2-IODOPHENYL TRIFLUOROMETHANESULFONATE is used as a research tool in academic and industrial laboratories for conducting experiments and developing new synthetic methodologies. Its application reason is based on its stability, reactivity, and selectivity, which are essential for exploring novel chemical reactions and pathways.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-IODOPHENYL TRIFLUOROMETHANESULFONATE is used as an intermediate in the synthesis of active pharmaceutical ingredients. Its application reason is due to its role in the preparation of key building blocks, which are then used to construct complex drug molecules with desired therapeutic properties.
Used in Material Science:
2-IODOPHENYL TRIFLUOROMETHANESULFONATE is also used in material science for the synthesis of novel materials with specific properties. Its application reason is attributed to its ability to participate in reactions that lead to the formation of materials with unique electronic, optical, or magnetic characteristics, which can be utilized in various high-tech applications.

InChI:InChI=1/C7H4F3IO3S/c8-7(9,10)15(12,13)14-6-4-2-1-3-5(6)11/h1-4H

Upstream product

• 358-23-6 trifluoromethylsulfonic anhydride 
• 533-58-4 2-Iodophenol 
• 108-95-2 phenol 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 17614-10-7 phenyl N-isopropylcarbamate 
• 864908-76-9 2-iodophenyl isopropylcarbamate 

Downstream Products

• 84-15-1 o-terphenyl 
• 17763-65-4 biphenyl-2-yl trifluoromethanesulfonate 
• 90-43-7 2-Phenylphenol 
• 199188-29-9 2-trifluoromethyl-1-trifluoromethanesulfonyloxybenzene 
• 1159-86-0 o-dibenzoylbenzene 
• 110349-12-7 o-n-butyliodobenzene 
• 104-51-8 1-butylbenzene 
• 1075184-55-2 1-(2-((E)-3-(trimethylsilyl)allyl)phenyl)piperidine 
• 1075184-54-1 ethyl 2-((E)-3-(trimethylsilyl)allyl)benzoate 
• 1075184-53-0 ((E)-3-(2-allylphenyl)prop-1-enyl)trimethylsilane 
• 611-64-3 9-methyl-acridine 
• 857934-92-0 4,4,5,5-tetramethyl-2-[2-(2-propenyl)phenyl]-1,3,2-dioxaborolane 
• 229-87-8 phenanthridine 
• 483-55-6 phthiocol 

Relevant articles and documents

Could London Dispersion Force Control Regioselective (2 + 2) Cyclodimerizations of Benzynes? YES: Application to the Synthesis of Helical Biphenylenes

In recent years, London dispersion interactions, which are the attractive component of the van der Waals potential, have been found to play an important role in controlling the regio- and/or stereoselectivity of various reactions. Particularly, the dispersion interactions between substrates and catalysts (or ligands) are dominant in various selective catalyzes. In contrast, repulsive steric interactions, rather than the attractive dispersion interactions, between bulky substituents are predominant in most of the noncatalytic reactions. Herein, we demonstrate the first example of London dispersion-controlled noncatalytic (2 + 2) cyclodimerization of substituted benzynes to selectively afford proximal biphenylenes in high yields and regioselectivities, depending on the extent of dispersion interactions in the substituents. This method can be applied for the synthesis of novel helical biphenylenes, which would be fascinating for chemists as these compounds are potential skeletons for ligands, catalysts, and medicines.

Synthesis of Stannylated Aryl Imines and Amines via Aryne Insertion Reactions into Sn?N Bonds

The reaction of in situ generated arynes with stannylated imines to provide ortho-stannyl-aniline derivatives is reported. The readily prepared trimethylstannyl benzophenone imine is introduced as an efficient reagent to realize the aryne σ-insertion reaction. The imine functionality is an established N-protecting group and insertions proceed with good yields and good to excellent regioselectivities. The product anilines are valuable starting materials for follow-up chemistry thanks to the rich chemistry offered by the trimethylstannyl moiety.

Facile synthesis of diverse o-iodoaryl triflates from o-silylaryl triflates by aluminum-mediated desilyliodination

A convenient method for preparing diverse o-iodoaryl triflates by the desilyliodination of o-silylaryl triflates has been developed. The treatment of o-silylaryl triflates with 1,3-diiodo- 5,5-dimethylhydantoin (DIH) in the presence of aluminum trichloride efficiently afforded the corresponding o-iodoaryl triflates, including those with multiple 1-iodo-2-(triflyloxy)arene moieties. Various multisubstituted o-iodoaryl triflates were easily prepared by the iridium-catalyzed CH borylation of readily available, simple o-silylaryl triflates, followed by deborylative transformations and subsequent desilyliodinaton.

Diaryl iodide salt compound as well as preparation method and application thereof

The invention discloses a diaryl iodide salt compound, as shown in Formula I which is shown in the specification: wherein R1 and R2 are independently selected from hydrogen, halogen, alkyl, alkoxy, halogen-substituted alkyl, halogen-substituted alkoxy. Th

Intramolecular Aryl Migration of Diaryliodonium Salts: Access to ortho-Iodo Diaryl Ethers

By using vicinal trifluoromethanesulfonate-substituted diaryliodonium salts, a novel approach was developed for the synthesis of ortho-iodo diaryl ethers by intramolecular aryl migration. The reaction conditions are mild with a broad substrate scope. Mechanistic insight suggests a sulfonyl-directed nucleophilic aromatic substitution pathway. Additionally, the product ortho-iodo diaryl ethers serve as versatile synthons as demonstrated with several coupling reactions. Furthermore, a useful thyroxine analogue of the 3-iodo-l-thyronine (3-T1) derivative was synthesized by this aryl migration procedure.

Auto-tandem catalysis: Synthesis of acridines by Pd-catalyzed C=C bond formation and C(sp2)-N cross-coupling

A facile palladium-catalyzed synthesis of acridines has been realized by consecutive C=C double bond formation and C-N cross-coupling. A variety of functionalized acridines can be accessed from easily available o-dihalobenzenes and N-tosylhydrazones in a single operation. This one-pot protocol has a wide scope with respect to both coupling partners, and provides an efficient route to functionalized acridine derivatives, which are generally difficult to synthesize by previously known methods.

Facile preparation of 2-iodophenyl trifluoromethanesulfonates: Superior aryne precursors

A comparative study of 3-methoxyaryne precursors revealed 2-iodo-3-methoxyphenyl triflate as the most effective in nonpolar solvent. Use of Hoppe's N-isopropyl carbamate allows for the systematic preparation of a variety of 2-iodophenyl triflates via a directed ortho-lithiation-iodination- decarbamation sequence. These steps are possible without isolation of the intermediate iodophenyl carbamates. Georg Thieme Verlag Stuttgart.

First synthesis of ortho-trifluoromethylated aryl triflates

An efficient method for the preparation of trifluoromethylated aryl triflates (trifluoromethanesulfonates) has been developed. Treatment of 2-iodophenol with trifluoromethanesulfonic anhydride in the presence of triethylamine gives triflate 3. Then, reaction of compound 3 with FSO2CF2CO2Me and CuI in DMF-HMPA affords trifluoromethylated aryl triflate 2. This reaction sequence is also successful for meta- and para-trifluoromethylated aryl triflates. Based on this methodology, the trifluoromethylated aryl triflate 11, a key intermediate for the preparation of the conformationally restricted retinoid 8 containing a trifluoromethyl group, has been synthesized. The cross-coupling of aryl triflate 11 with vinylstannane 17 under palladium catalysis provides compound 18, the methyl ester of retinoid 8, in moderate yield.