17417-09-3

Usage

Uses

Used in Pharmaceutical Industry:
2-Fluoro-5-nitrobenzonitrile is used as an intermediate in the synthesis of various pharmaceutical compounds for [application reason]. It plays a crucial role in the preparation of the following compounds:
1. 2-fluoro-5-aminobenzonitrile: 2-Fluoro-5-nitrobenzonitrile is used in the development of pharmaceuticals targeting specific diseases.
2. Ethyl 3-amino-5-nitro-benzo[b]thiophene-2-carboxylate: This derivative is utilized in the synthesis of drugs with potential therapeutic applications.
3. 1-methyl-5-nitro-1H-indazol-3-ylamine: 2-Fluoro-5-nitrobenzonitrile serves as a building block for the creation of new pharmaceutical agents with desired medicinal properties.

InChI:InChI=1/C8H4F3NS/c9-8(10,11)6-3-1-2-4-7(6)12-5-13/h1-4H

Upstream product

• 394-47-8 2-fluorobenzonitrile 
• 463-71-8 thiophosgene 
• 16588-02-6 4-chloro-3-cyanonitrobenzene 
• 10199-89-0 NBD chloride 
• 557-21-1 zinc(II) cyanide 
• 701-45-1 2-bromo-1-fluoro-4-nitrobenzene 

Downstream Products

• 32188-75-3 5-nitro-2-(piperidin-1-yl)benzonitrile 
• 731803-59-1 N-(2-Cycano-4-nitrophenyl)-n-butylamin 
• 85020-88-8 2-Benzylamino-5-nitro-benzonitrile 
• 63989-50-4 N-Acetyl-β-aminoethyl-2-cyano-4-nitro-1-phenylether 
• 34674-75-4 3-amino-5-nitrobenzo-[b]-thiophene-2-carboxylic acid methyl ester 
• 41339-17-7 5-nitro-1H-indazol-3-amine 
• 746676-52-8 2-methylamino-5-nitro-thiobenzamide 
• 746676-54-0 4-dimethylamino-2-(2-methylamino-5-nitro-phenyl)-4H-[1,3]thiazine-5,6-dicarboxylic acid dimethyl ester 
• 859206-13-6 2-(3-fluoro-benzyloxy)-5-nitro-benzonitrile 
• 918810-26-1 2-(Ethylthio)-5-nitrobenzonitrile 
• 918810-27-2 2-(ethylsulfonyl)-5-nitrobenzonitrile 
• 948992-52-7 2-(isopropylthio)-5-nitrobenzonitrile 
• 1126431-29-5 5-nitro-2-{[2-(1-pyrrolidinyl)ethyl]oxy}benzonitrile 
• 1079042-73-1 2-(3-aminophenoxy)-5-nitrobenzonitrile 

Relevant academic research and scientific papers

Synthesis, antiproliferative activity, and in silico insights of new 3-benzoylamino-benzo[ b ]thiophene derivatives

A new series of 3-benzoylamino-5-imidazol-5-yl-benzo[b]thiophenes and the parent amino derivatives were synthesized and screened as antitumor agents. All tested compounds showed concentration-dependent antiproliferative activity profile against HeLa cell

Design, synthesis, and biological evaluation of a new class of benzo[b]furan derivatives as antiproliferative agents, with in silico predicted antitubulin activity

A new series of 3-benzoylamino-5-(1H-imidazol-4-yl)methylaminobenzo[b]furans were synthesized and screened as antitumor agents. As a general trend, tested compounds showed concentration-dependent antiproliferative activity against HeLa and MCF-7 cancer cell lines, exhibiting GI50 values in the low micromolar range. In most cases, insertion of a methyl substituent on the imidazole moiety improved the antiproliferative activity. Therefore, methyl-imidazolyl-benzo[b]furans compounds were tested in cell cycle perturbation experiments, producing cell cycle arrest with proapoptotic effects. Their core similarity to known colchicine binding site binders led us to further study the structure features as antitubulin agents by in silico protocols.

Preparation of (Pentafluorosulfanyl)benzenes by Direct Fluorination of Diaryldisulfides: Synthetic Approach and Mechanistic Aspects

Direct fluorination of ortho-, meta- and para-substituted aromatic thiols and disulfides using elemental fluorine afforded substituted (pentafluorosulfanyl)benzenes. This work thus represents the first study of the scope and limitation of direct fluorination for the synthesis of new SF5-containing building blocks. Fluorinations in batch and flow modes were compared. A comprehensive computational study was carried out employing density functional and wave function methods to elucidate the reaction mechanism of the transformation of ArSF3 into ArSF5. Eliminating various nonradical pathways, it has been shown that the reaction proceeds by a radical mechanism, initiated by the attack of the F. on the ArSF3 moiety, propagated via an almost barrierless F2+ArSF4 .→ArSF5+F. step and terminated by the ArSF4 .+F.→ArSF5. Most of the calculated data are in very good agreement with experimental observations concerning the ortho-substituent effect on the reaction rates and yields.

Mild palladium-catalyzed cyanation of (hetero)aryl halides and triflates in aqueous media

A mild, efficient, and low-temperature palladium-catalyzed cyanation of (hetero)aryl halides and triflates is reported. Previous palladium-catalyzed cyanations of (hetero)aryl halides have required higher temperatures to achieve good catalytic activity. This current reaction allows the cyanation of a general scope of (hetero)aryl halides and triflates at 2-5 mol % catalyst loadings with temperatures ranging from rt to 40 °C. This mild method was applied to the synthesis of lersivirine, a reverse transcriptase inhibitor.

The preparation of trifluoromethyl aryl sulfides using KF and thiophosgene

The trifluoromethanethiolate anion may be generated in situ by the reaction of thiophosgene with potassium fluoride in acetonitrile. This system is used to prepare trifluoromethyl aryl sulfides from activated fluoro- and chloroaromatic substrates via nucleophilic substitution.

Synthesis of [1]Benzothieno[3,2-d]pyrimidines Substituted with Electron Donating Substituents on the Benzene Ring

Various 2-fluorobenzonitriles were converted to the corresponding 3-amino[1]benzothiophenecarboxylic acid esters, which in turn were annulated with formamidine or various equivalents to produce the desired tricyclic benzothienopyrimidines. Various methoxy and nitro/amino substituants were placed on the phenyl ring, requiring several different strategies to prepare the desired benzothiophenes. Several different pyrimidone annulations were also required. The use of an electron rich 2-bromobenzonitrile in a four-step one-pot low temperature lithiation sequence to produce highly electron-rich amino[1]benzothiophenecarboxylate esters is also described. The synthesis of 7-amino-8-fluoro[1]benzothieno[3,2-d]pyrimid-4(3H)-one was relatively straightforward, but synthesis of the corresponding 7-amino-8-protio analogue proved to be very difficult, and required several approaches before a successful one was found.

A convenient and new modified preparation of nitrosubstituted aryl fluorides

Nitrosubstituted aryl fluorides are easily prepared in good yields from chloro-nitrobenzenes and potassium fluoride in dimethyl sulfoxide and in the presence of polyethylene glycol 5090.