394-65-0

Usage

Uses

Used in Pharmaceutical Industry:
1-fluoroisoquinoline is used as a building block for the synthesis of biologically active compounds due to its unique structure and reactivity, which can contribute to the development of new pharmaceuticals.
Used in Analytical Chemistry and Bioimaging:
1-fluoroisoquinoline is used as a fluorescent probe for its potential applications in analytical chemistry and bioimaging, where its chemical properties can be leveraged to enhance imaging techniques and analytical processes.

Upstream product

• 19658-77-6 1-iodoisoquiniline 
• 19493-44-8 1-chloroisoquinoline 
• 1532-71-4 1-bromoisoquinoline 

Relevant academic research and scientific papers

Tetramethylammonium Fluoride Alcohol Adducts for SNAr Fluorination

Nucleophilic aromatic fluorination (SNAr) is among the most common methods for the formation of C(sp2)-F bonds. Despite many recent advances, a long-standing limitation of these transformations is the requirement for rigorously dry, aprotic conditions to maintain the nucleophilicity of fluoride and suppress the generation of side products. This report addresses this challenge by leveraging tetramethylammonium fluoride alcohol adducts (Me4NF·ROH) as fluoride sources for SNAr fluorination. Through systematic tuning of the alcohol substituent (R), tetramethylammonium fluoride tert-amyl alcohol (Me4NF·t-AmylOH) was identified as an inexpensive, practical, and bench-stable reagent for SNAr fluorination under mild and convenient conditions (80 °C in DMSO, without the requirement for drying of reagents or solvent). A substrate scope of more than 50 (hetero) aryl halides and nitroarene electrophiles is demonstrated.

Multiple Approaches to the in Situ Generation of Anhydrous Tetraalkylammonium Fluoride Salts for SNAr Fluorination Reactions

This article focuses on the development of practical approaches to the in situ generation of anhydrous fluoride salts for applications in nucleophilic aromatic substitution (SNAr) reactions. We report herein that a variety of combinations of inexpensive nucleophiles (e.g., tetraalkylammonium cyanide and phenoxide salts) and fluorine-containing electrophiles (e.g., acid fluoride, fluoroformate, benzenesulfonyl fluoride, and aryl fluorosulfonate derivatives) are effective for this transformation. Ultimately, we demonstrate that the combination of tetramethylammonium 2,6-dimethylphenoxide and sulfuryl fluoride (SO2F2) serves as a particularly practical route to anhydrous tetramethylammonium fluoride. This procedure is applied to the SNAr fluorination of a range of electron-deficient aryl and heteroaryl chlorides as well as nitroarenes.

PROCESS FOR FLUORINATING COMPOUNDS

Disclosed are mild temperature (e.g., from 0 to 80°C) SNAr fluorinations of a variety of halide and sulfonate substituted aryl and heteroaryl substrates using NMe4F.

Diastereoselective Synthesis of Dialkylated Bis(phosphino)ferrocenes: Their Use in Promoting Silver-Mediated Nucleophilic Fluorination of Chloroquinolines

The diastereoselective synthesis of dialkylated ferrocenyl bis(phosphane)s bearing aryl, alkyl, and hetero- or polycyclic substituents on the phosphino groups is reported, together with their characterization in the solid state by X-ray structure analysis

Anhydrous Tetramethylammonium Fluoride for Room-Temperature SNAr Fluorination

This paper describes the room-temperature SNAr fluorination of aryl halides and nitroarenes using anhydrous tetramethylammonium fluoride (NMe4F). This reagent effectively converts aryl-X (X = Cl, Br, I, NO2, OTf) to aryl-F under mild conditions (often room temperature). Substrates for this reaction include electron-deficient heteroaromatics (22 examples) and arenes (5 examples). The relative rates of the reactions vary with X as well as with the structure of the substrate. However, in general, substrates bearing X = NO2 or Br react fastest. In all cases examined, the yields of these reactions are comparable to or better than those obtained with CsF at elevated temperatures (i.e., more traditional halex fluorination conditions). The reactions also afford comparable yields on scales ranging from 100 mg to 10 g. A cost analysis is presented, which shows that fluorination with NMe4F is generally more cost-effective than fluorination with CsF.

Mild fluorination of chloropyridines with in situ generated anhydrous tetrabutylammonium fluoride

This paper describes the fluorination of nitrogen heterocycles using anhydrous NBu4F. Quinoline derivatives as well as a number of 3- and 5-substituted pyridines undergo high-yielding fluorination at room temperature using this reagent. These results with anhydrous NBu4F compare favorably to traditional halex fluorinations using alkali metal fluorides, which generally require temperatures of ≥100 °C.

Large-scale preparation of aromatic fluorides via electrophilic fluorination with functionalized aryl- or heteroarylmagnesium reagents

Functionalized aryl- or heteroarylmagnesium reagents, prepared from the corresponding bromides or iodides using halogen-magnesium exchange or direct magnesium insertion in the presence of lithium chloride, reacted smoothly with N-fluorobenzenesulfonimide, (PhSO2)2NF, in the mixed solvent (4:1 CH2Cl2-perfluorodecalin) to give the corresponding aromatic fluorides in moderate to good yields. Georg Thieme Verlag Stuttgart · New York.

Convenient electrophilic fluorination of functionalized aryl and heteroaryl magnesium reagents

"Chemical Equation Presented" Cive me an "F": Electrophilic fluorination of various aromatic and heteroaromatic Grignard reagents is smoothly performed with (PhSO2)2NF as fluorinating agent in a 4:1 mixture of CH2Cl2/ perfluorodecalin (see scheme). This solvent system allows minimization of most side reactions.