Month: October 2022

《Transition-metal-free, meta-selective arene CH direct α-aryl cyanomethylation of naphthalimide using a trifluoromethyl directing group》 was published in Dyes and Pigments in 2020. These research results belong to Li, Zheyao; Rao, Caihui; Chen, Lu; Fu, Chao; Zhu, Tingting; Chen, Xi; Liu, Chuanxiang. Safety of 2-(3-Bromophenyl)acetonitrile The article mentions the following:

A method for introducing a substituted aryl acetonitrile group at the C2 position of naphthalimide using trifluoromethyl as the directing group was reported. The transformation was operationally simple, requires mild conditions and was highly regioselective, without the need for a transition metal catalyst. This work provided a novel route for preparing α-diaryl nitrile derivatives I [R = Ph, 3-BrC6H4, 4-MeOC6H4, etc.]. After reading the article, we found that the author used 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Safety of 2-(3-Bromophenyl)acetonitrile)

According to other reports, 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5) is used in the preparation of diarylpyrimidines (DAPYs) as HIV-1 non-nucleoside reverse transcriptase inhibitors.Safety of 2-(3-Bromophenyl)acetonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

《Continuous flow Suzuki-Miyaura couplings in water under micellar conditions in a CSTR cascade catalyzed by Fe/ppm Pd nanoparticles》 was published in Green Chemistry in 2020. These research results belong to Wood, Alex B.; Nandiwale, Kakasaheb Y.; Mo, Yiming; Jin, Bo; Pomberger, Alexander; Schultz, Victor L.; Gallou, Fabrice; Jensen, Klavs F.; Lipshutz, Bruce H.. Synthetic Route of C7H4BrN The article mentions the following:

The first demonstration of aqueous surfactant-enabled Suzuki-Miyaura couplings run under flow conditions was described. In addition, use of an even more challenging heterogeneous nanoparticle catalyst, containing only 800 ppm of Pd (i.e., 0.08 mol%) in the form of Fe/ppm Pd nanoparticles, was sufficient using a continuous stirred-tank reactor (CSTR). In the part of experimental materials, we found many familiar compounds, such as 2-Bromobenzonitrile(cas: 2042-37-7Synthetic Route of C7H4BrN)

2-Bromobenzonitrile(cas: 2042-37-7) is a precursor to the quinazolinones, a class of drugs used to treat autoimmune diseases and coronary heart disease. This substrate molecule undergoes a palladium-catalyzed coupling reaction to form an aromatic ring. The light emission from this reaction can be seen in the reaction solution.Synthetic Route of C7H4BrN

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

《Transition metal- and solvent-free double hydroboration of nitriles》 was written by Bedi, Deepika; Brar, Aneelman; Findlater, Michael. Recommanded Product: 1194-02-1 And the article was included in Green Chemistry in 2020. The article conveys some information:

A highly efficient, room temperature double hydroboration of nitriles under transition metal-free and solvent-free conditions is reported. Sodium triethylborohydride is used as a catalyst and yields up to 99% are disclosed. Mechanistic studies reveal the reaction proceeds in a stepwise manner with initial formation of a boryl-imine which undergoes a second hydroboration to afford a diborylated amine product.4-Fluorobenzonitrile(cas: 1194-02-1Recommanded Product: 1194-02-1) was used in this study.

4-Fluorobenzonitrile(cas: 1194-02-1) is used as chemical intermediate, solvent for perfumes and pharmaceuticals, stabilizer for chlorinated solvents, HPLC analysis, catalyst and component of transition-metal complex catalysts.Recommanded Product: 1194-02-1

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

《Synthesis of Molybdenum Pincer Complexes and Their Application in the Catalytic Hydrogenation of Nitriles》 was written by Leischner, Thomas; Spannenberg, Anke; Junge, Kathrin; Beller, Matthias. Synthetic Route of C7H4FN And the article was included in ChemCatChem in 2020. The article conveys some information:

A series of molybdenum(0), (I) and (II) complexes ligated by different PNP and NNN pincer ligands were synthesized and structurally characterized. Along with previously described Mo-PNP complexes, all prepared compounds were tested in the catalytic hydrogenation of aromatic nitriles to primary amines. Among the applied catalysts, one is particularly well suited for the hydrogenation of electron-rich benzonitriles. Addnl., two aliphatic nitriles were transformed into the desired products in 80 and 86%, resp. Moreover, a catalytic intermediate was isolated and its role in the catalytic cycle was subsequently demonstrated. In the experiment, the researchers used many compounds, for example, 4-Fluorobenzonitrile(cas: 1194-02-1Synthetic Route of C7H4FN)

4-Fluorobenzonitrile(cas: 1194-02-1) is used as chemical intermediate, solvent for perfumes and pharmaceuticals, stabilizer for chlorinated solvents, HPLC analysis, catalyst and component of transition-metal complex catalysts.Synthetic Route of C7H4FN

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Lin, Yamei; Bu, Qingxia; Xu, Jiaxian; Liu, Xiao; Zhang, Xueping; Lu, Guo-Ping; Zhou, Baojing published their research in Molecular Catalysis in 2021. The article was titled 《Hf-MOF catalyzed Meerwein-Ponndorf-Verley (MPV) reduction reaction: Insight into reaction mechanism》.HPLC of Formula: 614-16-4 The article contains the following contents:

Hf-MOF-808 exhibits excellent activity and specific selectivity on the hydrogenation of carbonyl compounds via a hydrogen transfer strategy. Its superior activity than other Hf-MOFs is attributed to its poor crystallinity, defects and large sp. surface area, thereby containing more Lewis acid-base sites which promote this reaction. D. functional theory (DFT) computations are performed to explore the catalytic mechanism. The results indicate that alc. and ketone fill the defects of Hf-MOF to form a six-membered ring transition state (TS) complex, in which Hf as the center of Lewis stearic acid coordinates with the oxygen of the substrate mol., thus effectively promoting hydrogen transfer process. Other reactive groups, such as -NO2, C = C, -CN, of inadequate hardness or large steric hindrance are difficult to coordinate with Hf, thus weakening their catalytic effect, which explains the specific selectivity Hf-MOF-808 for reducing the carbonyl group. The experimental part of the paper was very detailed, including the reaction process of 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4HPLC of Formula: 614-16-4)

3-Oxo-3-phenylpropanenitrile(cas: 614-16-4) has been used to produce 2-benzoyl-3-furan-2-yl-acrylonitrile. It is an active methylene compound, useful in heterocyclic synthesis, e.g. polyfunctional pyridines and pyrimidines.HPLC of Formula: 614-16-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Kenari, Marziyeh E.; Putman, Joshua I.; Singh, Ravi P.; Fulton, Brandon B.; Phan, Huy; Haimour, Reem K.; Tse, Key; Berthod, Alain; Lovely, Carl J.; Armstrong, Daniel W. published their research in Molecules in 2021. The article was titled 《Enantiomeric separation of new chiral azole compounds》.HPLC of Formula: 1194-02-1 The article contains the following contents:

Twelve new azole compounds (rec/R/S)-I (Ar = Ph, Bn, Bz, allyl, 3,5-bis(trifluoromethyl)phenyl; R = 2,5-dioxo-1-phenylpyrrolidin-3-yl, 2-ethoxy-1-hydroxy-2-oxoethyl), (rec/R/S)-II (R1 = Ph, 4-chlorophenyl, 4-fluorophenyl, 4-methoxyphenyl) and (rec/R/S)-III were synthesized through an ene reaction involving methylidene heterocycles IV and V and N-phenylmaleimide, producing four oxazoles II (R = 2,5-dioxo-1-phenylpyrrolidin-3-yl), five thiazoles I (R = 2,5-dioxo-1-phenylpyrrolidin-3-yl), and one pyridine derivative, III and Et glyoxylate for an oxazole II (R = 2-ethoxy-1-hydroxy-2-oxoethyl) and a thiazole compd I (R = 2-ethoxy-1-hydroxy-2-oxoethyl). The twelve azoles I, II and III have a stereogenic center in their structure. Hence, a method to sep. the enantiomeric pairs, must be provided if any further study of chem. and pharmacol. importance of these compounds is to be accomplished. Six chiral stationary phases were assayed: four were based on macrocyclic glycopeptide selectors and two on linear carbohydrates, i.e., derivatized maltodextrin and amylose. The enantiomers of the entire set of new chiral azole compounds I, II and III were separated using three different mobile phase elution modes: normal phase, polar organic, and reversed phase. The most effective chiral stationary phase was the MaltoShell column, which was able to sep. ten of the twelve compounds I, II and III in one elution mode or another. Structural similarities in the newly synthesized oxazoles II provided some insights into possible chiral recognition mechanisms. The results came from multiple reactions, including the reaction of 4-Fluorobenzonitrile(cas: 1194-02-1HPLC of Formula: 1194-02-1)

4-Fluorobenzonitrile(cas: 1194-02-1) is used as chemical intermediate, solvent for perfumes and pharmaceuticals, stabilizer for chlorinated solvents, HPLC analysis, catalyst and component of transition-metal complex catalysts.HPLC of Formula: 1194-02-1

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Wang, Qile; Zheng, Nan published their research in Organic Letters on December 20 ,2019. The article was titled 《Difunctionalization of Cyclopropyl Amines with N-Iodosuccinimide (NIS) or in Situ Formed Cyanogen Iodide (ICN)》.Application of 1019607-55-6 The article contains the following contents:

Herein, a 1,3-difunctionalization of cyclopropylamines that serve as a π nucleophile in a two-electron (2e) SN2-like ring opening pathway is described. N-Iodosuccinimide (NIS) or in situ generated cyanogen iodide (ICN) is employed as electrophilic iodinating reagents in conjunction with TMSCN or succinimide to furnish multiple pairs of functional groups disposed in a 1,3-manner. This 2e ring opening manifold overcomes the constraint of previously reported 1e protocol as demonstrated by successful activation of monocyclic tertiary cyclopropylamines. In the experiment, the researchers used many compounds, for example, 4-(Cyclopropylamino)benzonitrile(cas: 1019607-55-6Application of 1019607-55-6)

4-(Cyclopropylamino)benzonitrile(cas: 1019607-55-6) belongs to anime. Many important products require amines as part of their syntheses. Methylamine is utilized in the production of the analgesic meperidine (trade name Demerol) and the photographic developer Metol (trademark), and dimethylamine is used in the synthesis of the antihistamine diphenhydramine (trade name Benadryl), the solvent dimethylformamide (DMF), and the rocket propellant 1,1-dimethylhydrazine. The synthesis of the insect repellent N,N-diethyl-m-toluamide (DEET) incorporates diethylamine while that of the synthetic fibre Kevlar requires aromatic amines.Application of 1019607-55-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2012,Huang, Liping; Liu, Yang; Xie, Fuchun; Hu, Youhong published 《An Organic Molecule Modulated Chemoselective Cyclization of Alkynyl Nitriles Tethered to 2-Alkyl Substituted Chromones with Multireactive Sites》.Organic Letters published the findings.Synthetic Route of C8H6BrN The information in the text is summarized as follows:

A small organic mol. phenylacetonitrile promoted chemoselective cyclization of (chromen-3-yl)alkynylnitriles to generate a novel tetracyclic or tricyclic chromone scaffold has been discovered. Importantly, the phenylacetonitrile serves as an anion transfer reagent changing the normal reaction of the substrate. In the experiment, the researchers used 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Synthetic Route of C8H6BrN)

2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5) has been used in the synthesis of 2-(1-cyano-1-(3-bromophenyl))methylidene-3-phenylthiazolidine-4,5-dione or a series of aminoethylbiphenyls, novel 5-HT7 receptor ligands.Synthetic Route of C8H6BrN

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2014,Al Otaibi, Ahmed; Gordon, Christopher P.; Gilbert, Jayne; Sakoff, Jennette A.; McCluskey, Adam published 《The influence of ionic liquids on the Knoevenagel condensation of 1H-pyrrole-2-carbaldehyde with phenyl acetonitriles – cytotoxic 3-substituted-(1H-pyrrol-2-yl)acrylonitriles》.RSC Advances published the findings.Name: 2-(3-Bromophenyl)acetonitrile The information in the text is summarized as follows:

The Knoevenagel condensation of a series of substituted Ph acetonitriles with 1H-pyrrole-2-carbaldehyde was examined in seven 1-butyl-3-methylimidazolium based ionic liquids and three protic ionic liquids Of these [BMIM][Br] and [BMIM][OH], with catalytic piperidine, proved most efficient affording 3-substituted-(1H-pyrrol-2-yl)acrylonitriles 3-17 in good to excellent yields (98%) while utilization of the protic ionic liquid Pr ammonium nitrate resulted in reduced yields (0-66%). Screening of the 3-substituted-(1H-pyrrol-2-yl)acrylonitriles analogs 3-17 against a panel of 11 cancer cell lines and one normal cell line allowed the identification of a series of compounds with broad spectrum cytotoxicity, but more interestingly a significant degree of MCF-7 breast cancer cell line specificity was evident with 6 (7 to >25 fold) and 13 (5.7 to >80 fold). Other analogs show high level of efficacy against specific cell lines with 10 showing excellent activity against MCF-7 (GI50 = 1.7 μM) and A431 (GI50 = 2.8 μM) cell lines. The most promising of the compounds identified herein were the 4-CF3 substituted 10 and the 3,4-dichloro substituted 13 with excellent activities against MCF-7 and A431 cell lines. The 3,4-dichloro-13 was a 0.56 μM potent inhibitor of MCF-7 cell growth. The results came from multiple reactions, including the reaction of 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Name: 2-(3-Bromophenyl)acetonitrile)

According to other reports, 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5) is used in the preparation of diarylpyrimidines (DAPYs) as HIV-1 non-nucleoside reverse transcriptase inhibitors.Name: 2-(3-Bromophenyl)acetonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2018,Soft Matter included an article by Pocock, Emily E.; Mandle, Richard J.; Goodby, John W.. Name: 4-Bromo-2-fluorobenzonitrile. The article was titled 《Molecular shape as a means to control the incidence of the nanostructured twist bend phase》. The information in the text is summarized as follows:

Eleven novel materials I [R = 4-(4-CNC6H4)C6H4, 4-(3,4-di-FC6H4)C6H4, 4-(4-F5SC6H4)C6H4, etc.] with all found to exhibited the twist-bend phase and a linear relationship between TN-I and TTB-N were prepared and studied. A computational study of the conformational landscape revealed the octamethyleneoxy spacer to had a broader distribution of bend-angles than the nonamethylene equivalent, leading to reductions in the thermal stability of the TB phase. This result indicates that a tight distribution of bend-angles should stabilize the TB phase and lead to direct TB-Iso phase transitions, and conversely a broader distribution should destabilize the TB phase which may allowed new states of matter that were occluded by the incidence of this phase to be revealed. In the part of experimental materials, we found many familiar compounds, such as 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Name: 4-Bromo-2-fluorobenzonitrile)

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts