4949-13-7

Usage

Uses

Used in Pharmaceutical Industry:
2-Fluoropyrazine 98 is used as a building block for the synthesis of various pharmaceuticals and agrochemicals. Its unique chemical properties and high purity level make it a valuable component in the development of new drugs and therapeutic agents.
Used in Chemical Industry:
2-Fluoropyrazine 98 is used as a reagent in organic synthesis and as an intermediate in the production of fine chemicals. Its versatility and compatibility with other chemicals allow for its use in a wide range of chemical reactions and processes.
Used in Research and Development:
2-Fluoropyrazine 98 is utilized in research and development for the exploration of new chemical reactions, synthesis pathways, and potential applications in various fields. Its unique properties and high purity make it an ideal candidate for scientific investigations and experimental studies.

Upstream product

• 14508-49-7 2-chloropyrazin 

Downstream Products

• 206278-19-5 2-fluoro-3-(1-phenylhydroxymethyl)pyrazine 
• 206278-44-6 2-(Diphenyl-trimethylsilanyloxy-methyl)-3-fluoro-pyrazine 
• 206278-20-8 2-fluoro-3-(diphenylhydroxymethyl)pyrazine 
• 206278-28-6 2-acetyl-3-fluoropyrazine 
• 206278-24-2 2-fluoro-3-formylpyrazine 
• 206278-26-4 2-fluoro-3-iodopyrazine 
• 421663-65-2 2-fluoro-3-[1-(4-n-decyloxyphenyl)hydroxymethyl]pyrazine 
• 421663-69-6 2-fluoro-3-[1-(4-n-dodecyloxyphenyl)hydroxymethyl]pyrazine 
• 21352-21-6 2-(N-acetylamino)pyrazine 
• 29460-97-7 2-phenylpyrazine 

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.

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.

Acyl azolium fluorides for room temperature nucleophilic aromatic fluorination of chloro- and nitroarenes

The reaction of acid fluorides with N-heterocyclic carbenes (NHCs) produces anhydrous acyl azolium fluorides. With appropriate selection of acid fluoride and NHC, these salts can be used for the room temperature SNAr fluorination of a variety of aryl chlorides and nitroarenes.

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.

Room-temperature nucleophilic aromatic fluorination: Experimental and theoretical studies

(Chemical Equation Presented) Taming the reagent: The use of anhydrous tetrabutylammonium fluoride (TBAFanh) in nucleophilic aromatic substitution reactions, including variants of the selective halogen-exchange and fluorodenitration processes (see scheme), was investigated. It was shown that TBAFanh permits these reactions to be performed under surprisingly mild conditions if it is used in relatively nonpolar media.

Functionalization by metallation of fluoropyrazine. Diazines XXI

Lithiation of fluoropyrazine followed by quenching with various electrophiles was successfully achieved and was used to synthesize new pyrazine derivatives. A further lithiation of 2-fluoro-3-substitute, pyrazines allowed access to 2,3,6-trisubstituted pyridazine derivatives. As an application, a one-pot synthesis of a quinuclidinylfluoropyrazine has been performed. When the 3-substituent bears a TMS protected alcohol, functionalization via metallation at C6 position provides tetrasubstituted pyrazines in good yield.

Halogen-Exchange Fluorination of Aromatic Halides with HF or HF-Base

Heteroatomic halides such as 2-chloropyrimidines and 2-chloropyridines, and 2,4-dinitrochlorobenzene underwent halogen-exchange fluorination with the treatment of HF or HF-base solutions to afford the corresponding fluorides in good yields.

NUCLEOPHILIC FLUORINATION OF CHLORINATED N-HETEROCYCLES WITH TETRABUTYLPHOSPHONIUM HYDROGENDIFLUORIDE AND DIHYDROGENTRIFLUORIDE

Fluorination of various chlorinated N-heterocycles with tetrabutylphosphonium hydrogendifluoride (1) or dihydrogentrifluoride (2) readilly proceeded in high yields under mild conditions.