Category: 105942-08-3

In 2017,Wang, Shao-Feng; Cao, Xiao-Ping; Li, Yang published 《Efficient Aryl Migration from an Aryl Ether to a Carboxylic Acid Group To Form an Ester by Visible-Light Photoredox Catalysis》.Angewandte Chemie, International Edition published the findings.Category: nitriles-buliding-blocks The information in the text is summarized as follows:

The authors have developed a highly efficient aryl migration from an aryl ether to a carboxylic acid group through retro-Smiles rearrangement by visible-light photoredox catalysis at ambient temperature Transition metals and a stoichiometric oxidant and base are avoided in the transformation. Inspired by the high efficiency of this transformation and the fundamental importance of C-O bond cleavage, the authors developed a novel approach to the C-O cleavage of a biaryl ether to form two phenolic compounds, as demonstrated by a 1-pot, two-step gram-scale reaction under mild conditions. The aryl migration exhibits broad scope and can be applied to the synthesis of pharmaceutical compounds, such as guacetisal. Primary mechanistic studies indicate that the catalytic cycle occurs by a reductive quenching pathway.4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Category: nitriles-buliding-blocks) was used in this study.

4-Bromo-2-fluorobenzonitrile(cas:105942-08-3) is used as a reagent in the synthesis of picolinamide derivatives as a novel class of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibitors.Category: nitriles-buliding-blocks 4-Bromo-2-fluorobenzonitrile is also used in the preparation of fluorinated CB2 receptor agonists for PET imaging.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2019,Organic Process Research & Development included an article by Remarchuk, Travis; Angelaud, Remy; Askin, David; Kumar, Archana; Thompson, Andrew S.; Cheng, Hua; Reichwein, John F.; Chen, Yanping; St-Jean, Frederic. Reference of 4-Bromo-2-fluorobenzonitrile. The article was titled 《Manufacture of the PI3K β-Sparing Inhibitor Taselisib. Part 1: Early-Stage Development Routes to the Bromobenzoxazepine Core》. The information in the text is summarized as follows:

Two convergent regioselective routes for the synthesis of the tetracyclic imidazobenzoxazepine triazole I, a key intermediate toward the synthesis of taselisib, are described. In the first-generation route, a chemoselective Negishi cross-coupling reaction was developed between iodoimidazole II and 1-isopropyl-3-methyl-1H-1,2,4-triazole, which enabled the delivery of initial kilogram quantities of I. Because of the inefficiencies in the preparation of the imidazole II, a second-generation route via a highly regioselective imidazole ring formation between α-chloroketone III and aryl amidine IV was developed. The resulting imidazole V provided the handle to efficiently install the seven-membered benzoxazepine ring system in one pot with two-step N-alkylation and SNAr tandem reactions. The experimental process involved the reaction of 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Reference of 4-Bromo-2-fluorobenzonitrile)

4-Bromo-2-fluorobenzonitrile(cas:105942-08-3) is used as a reagent in the synthesis of picolinamide derivatives as a novel class of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibitors.Reference of 4-Bromo-2-fluorobenzonitrile 4-Bromo-2-fluorobenzonitrile is also used in the preparation of fluorinated CB2 receptor agonists for PET imaging.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Faraggi, Tomer M.; Rouget-Virbel, Caroline; Rincon, Juan A.; Barberis, Mario; Mateos, Carlos; Garcia-Cerrada, Susana; Agejas, Javier; de Frutos, Oscar; MacMillan, David W. C. published their research in Organic Process Research & Development in 2021. The article was titled 《Synthesis of enantiopure unnatural amino acids by metallaphotoredox catalysis》.Category: nitriles-buliding-blocks The article contains the following contents:

We describe herein a two-step process for the conversion of serine to a wide array of optically pure unnatural amino acids. This method utilizes a photocatalytic cross-electrophile coupling between a bromoalkyl intermediate and a diverse set of aryl halides to produce artificial analogs of phenylalanine, tryptophan, and histidine. The reaction is tolerant of a broad range of functionalities and can be leveraged toward the scalable synthesis of valuable pharmaceutical scaffolds via flow technol. The experimental part of the paper was very detailed, including the reaction process of 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Category: nitriles-buliding-blocks)

4-Bromo-2-fluorobenzonitrile(cas:105942-08-3) is used as a reagent in the synthesis of picolinamide derivatives as a novel class of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibitors.Category: nitriles-buliding-blocks 4-Bromo-2-fluorobenzonitrile is also used in the preparation of fluorinated CB2 receptor agonists for PET imaging.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 105942-08-3In 2019 ,《Manufacture of the PI3K β-Sparing Inhibitor Taselisib. Part 2: Development of a Highly Efficient and Regioselective Late-Stage Process》 was published in Organic Process Research & Development. The article was written by St-Jean, Frederic; Remarchuk, Travis; Angelaud, Remy; Carrera, Diane E.; Beaudry, Danial; Malhotra, Sushant; McClory, Andrew; Kumar, Archana; Ohlenbusch, Gerd; Schuster, Andreas M.; Gosselin, Francis. The article contains the following contents:

A highly efficient and regioselective manufacturing route for the phosphoinositide 3-kinase β-sparing inhibitor taselisib (I) was developed. Highlights of the synthesis include: (1) magnesium-mediated formation of a challenging cyclic amidine; (2) regioselective imidazole construction via alkylation/condensation with bromopyruvic acid; and (3) triazole formation with 2-iso-Pr acetamidrazone to generate the key bromobenzoxazepine core intermediate. Subsequent highly efficient one-pot palladium-catalyzed Miyaura borylation/Suzuki cross-coupling/saponification, followed by a 1,1′-carbonyldiimidazole-mediated coupling with ammonia, led to the pentacyclic taselisib. This new synthetic approach provides a more efficient route to taselisib with a significant decrease in process mass intensity compared to the previous early development routes to the bromobenzoxazepine core. Finally, implementation of a controlled crystallization provided the active pharmaceutical ingredient with the desired polymorphic form.4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Related Products of 105942-08-3) was used in this study.

4-Bromo-2-fluorobenzonitrile(cas:105942-08-3) is used as a OLED intermediate, Pharmaceutical, electronic and chemical intermediate.Related Products of 105942-08-3 It is used in the synthesis of heterocycles and liquid crystals.

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Campbell, Mark W.; Yuan, Mingbin; Polites, Viktor C.; Gutierrez, Osvaldo; Molander, Gary A. published their research in Journal of the American Chemical Society in 2021. The article was titled 《Photochemical C-H Activation Enables Nickel-Catalyzed Olefin Dicarbofunctionalization》.Formula: C7H3BrFN The article contains the following contents:

Herein, the implementation of efficient, sustainable, diaryl ketone hydrogen-atom transfer (HAT) catalysis to activate native C-H bonds for multicomponent dicarbofunctionalization of alkenes was reported. The ability to forge new carbon-carbon bonds between reagents typically viewed as commodity solvents provided a new, more atom-economic outlook for organic synthesis. Through detailed exptl. and computational investigation, the critical effect of hydrogen bonding on the reactivity of this transformation was uncovered. In the experimental materials used by the author, we found 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Formula: C7H3BrFN)

4-Bromo-2-fluorobenzonitrile(cas:105942-08-3) is used as a reagent in the synthesis of picolinamide derivatives as a novel class of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibitors.Formula: C7H3BrFN 4-Bromo-2-fluorobenzonitrile is also used in the preparation of fluorinated CB2 receptor agonists for PET imaging.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2022,Bawden, Joseph C.; Francis, Paul S.; DiLuzio, Stephen; Hayne, David J.; Doeven, Egan H.; Truong, Johnny; Alexander, Richard; Henderson, Luke C.; Gomez, Daniel E.; Massi, Massimiliano; Armstrong, Blake I.; Draper, Felicity A.; Bernhard, Stefan; Connell, Timothy U. published an article in Journal of the American Chemical Society. The title of the article was 《Reinterpreting the Fate of Iridium(III) Photocatalysts-Screening a Combinatorial Library to Explore Light-Driven Side-Reactions》.Electric Literature of C7H3BrFN The author mentioned the following in the article:

Photoredox catalysts are primarily selected based on ground and excited state properties, but their activity is also intrinsically tied to the nature of their reduced (or oxidized) intermediates. Catalyst reactivity often necessitates an inherent instability, thus these intermediates represent a mechanistic turning point that affords either product formation or side-reactions. In this work, we explore the scope of a previously demonstrated side-reaction that partially saturates one pyridine ring of the ancillary ligand in heteroleptic iridium(III) complexes. Using high-throughput synthesis and screening under photochem. conditions, we identified different chem. pathways, ultimately governed by ligand composition The ancillary ligand was the key factor that determined photochem. stability. Following photoinitiated electron transfer from a sacrificial tertiary amine, the reduced intermediate of complexes containing 1,10-phenanthroline derivatives exhibited long-term stability. In contrast, complexes containing 2,2′-bipyridines were highly susceptible to hydrogen atom transfer and ancillary ligand modification. Detailed characterization of selected complexes before and after transformation showed differing effects on the ground and excited state reduction potentials dependent on the nature of the cyclometalating ligands and excited states. The implications of catalyst stability and reactivity in chem. synthesis was demonstrated in a model photoredox reaction. The results came from multiple reactions, including the reaction of 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Electric Literature of C7H3BrFN)

4-Bromo-2-fluorobenzonitrile(cas:105942-08-3) is used as a reagent in the synthesis of picolinamide derivatives as a novel class of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibitors.Electric Literature of C7H3BrFN 4-Bromo-2-fluorobenzonitrile is also used in the preparation of fluorinated CB2 receptor agonists for PET imaging.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

《Cobalt-Catalyzed Cross-Coupling of Functionalized Alkylzinc Reagents with (Hetero)Aryl Halides》 was published in Angewandte Chemie, International Edition in 2020. These research results belong to Lutter, Ferdinand H.; Grokenberger, Lucie; Spiess, Philipp; Hammann, Jeffrey M.; Karaghiosoff, Konstantin; Knochel, Paul. HPLC of Formula: 105942-08-3 The article mentions the following:

A combination of 10% CoCl2 and 20% 2,2′-bipyridine ligands enables cross-coupling of functionalized primary and secondary alkylzinc reagents RZnY (R = 3-phenylpropyl, 3-(2,5-dimethyl-1H-pyrrol-1-yl)propyl, cyclopropyl, etc.; Y = Cl, Br) with various (hetero)aryl halides R1X (R1 = 5-cyanopyridin-2-yl, quinolin-2-yl, pyrimidin-2-yl, etc.; X = Cl, Br). Couplings with 1,3- and 1,4-substituted cycloalkylzinc reagents R2ZnI (R2 = 3-methylcyclohexyl, 4-(1H-pyrrol-1-yl)cyclohexyl, (4R,4aS,6R,8aR)-4,4a-dimethyl-6-(propan-2-yl)-decahydronaphthalen-2-yl, etc.) proceeded diastereoselectively leading to functionalized heterocycles R1R2 with high diastereoselectivities of up to 98:2. Furthermore, alkynyl bromides R3CCBr (R3 = Ph, tris(propan-2-yl)silyl) react with primary and secondary alkylzinc reagents RZnY (R = 2-(1,3-dioxan-2-yl)ethyl, 4-phenylcyclohexyl; Y = Cl, I) providing the alkylated alkynes RCCR3. In addition to this study using 4-Bromo-2-fluorobenzonitrile, there are many other studies that have used 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3HPLC of Formula: 105942-08-3) was used in this study.

4-Bromo-2-fluorobenzonitrile(cas:105942-08-3) is used as a reagent in the synthesis of picolinamide derivatives as a novel class of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibitors.HPLC of Formula: 105942-08-3 4-Bromo-2-fluorobenzonitrile is also used in the preparation of fluorinated CB2 receptor agonists for PET imaging.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Li, Haoyu; Liu, Yuliang; Chiba, Shunsuke published their research in Chemical Communications (Cambridge, United Kingdom) in 2021. The article was titled 《Anti-Markovnikov hydroarylation of alkenes via polysulfide anion photocatalysis》.Formula: C7H3BrFN The article contains the following contents:

A protocol for anti-Markovnikov hydroarylation of alkenes, e.g., 2,3-dihydrofuran with aryl halides ArX (Ar = (4-CO2CH3)C6H4, 2-naphthyl, 5-cyanothiophen-2-yl, etc.; X = Br, Cl) has been developed using polysulfide anions as photocatalysts in the presence of the Hantzsch ester and water under irradiation with visible light. The results came from multiple reactions, including the reaction of 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Formula: C7H3BrFN)

4-Bromo-2-fluorobenzonitrile(cas:105942-08-3) is used as a reagent in the synthesis of picolinamide derivatives as a novel class of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibitors.Formula: C7H3BrFN 4-Bromo-2-fluorobenzonitrile is also used in the preparation of fluorinated CB2 receptor agonists for PET imaging.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2017,Hendrick, Charles E.; Bitting, Katie J.; Cho, Seoyoung; Wang, Qiu published 《Site-Selective Copper-Catalyzed Amination and Azidation of Arenes and Heteroarenes via Deprotonative Zincation》.Journal of the American Chemical Society published the findings.Product Details of 105942-08-3 The information in the text is summarized as follows:

Arene amination is achieved by site-selective C-H zincation followed by copper-catalyzed coupling with O-benzoylhydroxylamines under mild conditions. Key to this success is ortho-zincation mediated by lithium amidodiethylzincate base that is effective for a wide range of arenes, including nonactivated arenes bearing simple functionalities such as fluoride, chloride, ester, amide, ether, nitrile, and trifluoromethyl groups as well as heteroarenes including indole, thiophene, pyridine, and isoquinoline. An analogous C-H azidation is also accomplished using azidoiodinane for direct introduction of a useful azide group onto a broad scope of arenes and heteroarenes. These new transformations offer rapid access to valuable and diverse chem. space of aminoarenes. Their broad applications in organic synthesis and drug discovery are demonstrated in the synthesis of novel analogs of natural product (-)-nicotine and antidepressant sertraline by late-stage amination and azidation reactions. After reading the article, we found that the author used 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Product Details of 105942-08-3)

4-Bromo-2-fluorobenzonitrile(cas:105942-08-3) is used as a reagent in the synthesis of picolinamide derivatives as a novel class of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibitors.Product Details of 105942-08-3 4-Bromo-2-fluorobenzonitrile is also used in the preparation of fluorinated CB2 receptor agonists for PET imaging.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The author of 《Protective effects of piper betel phenol, hydroxychavicol and its derivatives against rotenone induced neurotoxicity: synthesis, in vitro and in vivo efficacy studies》 were Ghanta, Venkata Rao; Pasula, Aparna; Pindiprolu, Sai Kiran S. S.; Krishnamurthy, Praveen T.; Ravi, Chandran J. K.; Raman, Balamurali. And the article was published in World Journal of Pharmaceutical Research in 2019. Quality Control of 4-Bromo-2-fluorobenzonitrile The author mentioned the following in the article:

Hydroxychavicol or 4-Allylpyrocatechol (4-APC) is a Piper betel phenol, reported to modulate vital pathways involved in inflammation and oxidative stress. However, the potential neuro protective benefits of 4APC against neurodegeneration, where similar pathways are involved was not reported and hence 4APC and its derivatives (3a – 3j) were evaluated for their possible neuroprotective activity against rotenone induced neurotoxicity. In the present study 4-allyl pyrocatechol (APC) and its derivatives (3a – 3j) were synthesized via heck coupling with aryl bromides and evaluated for their possible in vitro and in vivo neuroprotective activity against rotenone induced neurotoxicity in SH-SY5Y cell lines and in Swiss albino mice, resp. In the in vitro studies, among the tested compounds, the 4APC and its derivative, 3c, have shown significant protection against rotenone induced cytotoxicity. In mice, these 2 mols. significantly prevent the rotenone (3 mg/kg, s.c.) induced changes in grip strength, locomotor activity and oxidative & inflammatory stress markers at a tested oral dose of 20/mg/kg. The results came from multiple reactions, including the reaction of 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Quality Control of 4-Bromo-2-fluorobenzonitrile)

4-Bromo-2-fluorobenzonitrile(cas:105942-08-3) is used as a OLED intermediate, Pharmaceutical, electronic and chemical intermediate.Quality Control of 4-Bromo-2-fluorobenzonitrile It is used in the synthesis of heterocycles and liquid crystals.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts