1121-86-4

Usage

Uses

Used in Pharmaceutical Industry:
1-Fluoro-3-iodobenzene is used as a key intermediate for the synthesis of 4-substituted benzo[b]thiophene-2-carboxamidines. These compounds are important in the development of pharmaceuticals, particularly for the preparation of methyl 4-iodobenzo[b]thiophene-2-carboxylate, which serves as a crucial step in the production of various drug molecules.
Used in Organic Synthesis:
1-Fluoro-3-iodobenzene is utilized as a reactant in palladium-catalyzed hydroarylation of arylpropiolamides. This reaction is a valuable method for the formation of carbon-carbon bonds in organic chemistry, allowing for the creation of complex molecular structures that are essential in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and advanced materials.

InChI:InChI=1/C6H5BBrFO2/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,10-11H

Upstream product

• 20460-04-2 m-Fluor-benzoldiazonium-ion 
• 7217-41-6 (3-fluorophenyl)trimethylsilane 
• 462-06-6 fluorobenzene 
• 108-95-2 phenol 
• 768-35-4 3-fluorophenylboronic acid 
• 626-01-7 3-Iodoaniline 
• 57606-65-2 m-fluorophenyl trifluoromethanesulfonate 
• 128254-27-3 2-Fluoro-1,4-bis-trimethylsilanyl-benzene 
• 372-19-0 meta-fluoroaniline 

Downstream Products

• 2367-22-8 3-fluorobiphenyl 
• 120866-16-2 3-iodosylfluorobenzene 
• 40276-34-4 (3-Fluoro-phenyl)-diphenyl-amine 
• 1005407-88-4 5-(3-Fluoro-phenyl)-pent-4-yn-1-ol 
• 23588-07-0 diethyl (3-fluorophenyl)phosphonate 
• 40154-91-4 1-fluoro-3-phenylsulfanyl-benzene 
• 51788-78-4 4-fluoro-2'-iodo-acetophenone 
• 462-06-6 fluorobenzene 
• 696-39-9 1-fluoro-3-ethylbenzene 
• 74325-03-4 methyl (E)-m-fluorocinnamate 
• 87895-07-6 1-tosyl-2,5-dimethyl-1H-pyrrol-3-carboxylic acid ethyl ester 
• 211512-98-0 2-(3-fluorophenyl)propiolamide 

Relevant academic research and scientific papers

Synthesis of biaryl compounds via Suzuki homocoupling reactions catalyzed by metal organic frameworks encapsulated with palladium nanoparticles

Heterogeneous homocoupling reactions of phenylboronic acids were greatly accelerated via Suzuki homocoupling reactions. In this work, a tandem route was designed which firstly one part of phenylboronic acids reacted with iodine to form iodobenzenes, then another part of phenylboronic acids coupled with iodobenzenes to produce biaryl compounds. The tandem reaction were catalyzed by a bifunctional heterogeneous catalyst of metal organic frameworks encapsulated with palladium nanoparticles (Pd?MOFs). This strategy for forming symmetric C-C bond between benzene rings has obvious advantages such as high efficiency, easy separation, good recyclability and no addition of toxic halogenated benzene.

A meta-Selective C?H Alumination of Mono-Substituted Benzene by Using An Alkyl-Substituted Al Anion through Hydride-Eliminating SNAr Reaction

Reaction of an Al-centered anion with toluene proceeded to form C?H cleaved product with a perfect meta-selectivity and a relatively small kinetic isotope effect (KIE, kH/kD=1.51). DFT calculations suggested a two-step reaction mechanism and electronically controlled meta-selectivity arising from the electron-donating methyl group. The reaction with other mono-substituted arenes was also investigated.

Electrochemical Synthesis of Aryl Iodides by Anodic Iododesilylation

An electrochemical access to iodinated aromatic compounds starting from trimethylsilyl-substituted arenes is presented. By design of experiments, highly efficient and mild conditions were identified for a wide range of substrates. A functional group stability test and the synthesis of an important 3-iodobenzylguanidine radiotracer illustrate the scope of this process.

Hypervalent Iodine(III)-Catalyzed Balz–Schiemann Fluorination under Mild Conditions

An unprecedented hypervalent iodine(III) catalyzed Balz–Schiemann reaction is described. In the presence of a hypervalent iodine compound, the fluorination reaction proceeds under mild conditions (25–60 °C), and features a wide substrate scope and good functional-group compatibility.

Application of trivalent iodine compounds as catalysts in Bal-Schiemann reaction

The invention discloses an application of trivalent iodine compounds shown in formula I and/or II in the description and used as catalysts in Bal-Schiemann reaction. The trivalent iodine compounds areused as the catalysts in the Bal-Schiemann reaction, so that the Bal-Schiemann reaction can be conducted at room temperature or near room temperature when a thermochemical method is used, and the reaction has mild reaction conditions, wide substrate use range and short reaction time, and is safe and easy to operate, products are easy to separate, and raw materials are simple and low in toxicity.

METHOD FOR AROMATIC FLUORINATION

Disclosed is a fluorination method comprising providing an aryl fluorosuifonate and a fluorinating reagent to a reaction mixture; and reacting the aryl fluorosuifonate and the fluorinating reagent to provide a fluorinated aryl species. Also disclosed is a fluorination method comprising providing, a salt comprising a cation and an aryloxyiate, and SO2F2 to a reaction mixture; reacting the SO2F2 and the ammonium salt to provide a fluorinated aryl species. Further disclosed a fluorination method comprising providing a compound having the structure Ar-OH to a reaction mixture; where A is an aryl or heteroaryl; providing SO2F2 to the reaction mixture; providing a fluorinating reagent to the reaction mixture; reacting the SO2F2, the fluorinating reagent and the compound having the structure Ar-OH to provide a fluorinated aryl species having the structure Ar-F.

Nucleophilic deoxyfluorination of phenols via aryl fluorosulfonate intermediates

This report describes a method for the deoxyfluorination of phenols with sulfuryl fluoride (SO2F2) and tetramethylammonium fluoride (NMe4F) via aryl fluorosulfonate (ArOFs) intermediates. We first demonstrate that the reaction of ArOFs with NMe4F proceeds under mild conditions (often at room temperature) to afford a broad range of electronically diverse and functional group-rich aryl fluoride products. This transformation was then translated to a one-pot conversion of phenols to aryl fluorides using the combination of SO2F2 and NMe4F. Ab initio calculations suggest that carbon-fluorine bond formation proceeds via a concerted transition state rather than a discrete Meisenheimer intermediate.

Simple and Efficient Generation of Aryl Radicals from Aryl Triflates: Synthesis of Aryl Boronates and Aryl Iodides at Room Temperature

Despite the wide use of aryl radicals in organic synthesis, current methods to prepare them from aryl halides, carboxylic acids, boronic acids, and diazonium salts suffer from limitations. Aryl triflates, easily obtained from phenols, are promising aryl radical progenitors but remain elusive in this regard. Inspired by the single electron transfer process for aryl halides to access aryl radicals, we developed a simple and efficient protocol to convert aryl triflates to aryl radicals. Our success lies in exploiting sodium iodide as the soft electron donor assisted by light. This strategy enables the scalable synthesis of two types of important organic molecules, i.e., aryl boronates and aryl iodides, in good to high yields, with broad functional group compatibility in a transition-metal-free manner at room temperature. This protocol is anticipated to find potential applications in other aryl-radical-involved reactions by using aryl triflates as aryl radical precursors.

ISOQUINOLINES USEFUL AS INDUCIBLE NITRIC OXIDE SYNTHASE INHIBITORS

Disclosed herein are new isoquinoline compounds and compositions and their application as pharmaceuticals for the treatment of disease. Methods of inhibition of nitric oxide synthase activity in a human or animal subject are also provided for the treatment disease.

Method for producing tetrakis ( fluoroaryl) borate-magnesium compound

Fluoroaryl magnesium halide is reacted with a boron compound so that a molar ratio of the fluoroaryl magnesium halide to the boron compound is not less than 3.0 and not more than 3.7, so as to produce a tetrakis (fluoroaryl) borate·magnesium compound. With this method, there occurs no hydrogen fluoride which corrodes a producing apparatus and requires troublesome waste water treatment.