Month: October 2022

《One-pot synthesis of new aza- and diaza-aminophenanthrenes》 was published in Tetrahedron in 2011. These research results belong to Rochais, Christophe; Yougnia, Rodrigue; Cailly, Thomas; Sopkova-de Oliveira Santos, Jana; Rault, Sylvain; Dallemagne, Patrick. Name: 2-(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile The article mentions the following:

The synthesis of a series of benzo(iso)quinoline and phenanthroline derivatives has been achieved using an efficient one-pot procedure. It proceeds through a Suzuki-Miyaura cross-coupling followed by a Dieckmann-Thorpe ring closure under microwave irradiation and provides easy access to building blocks not readily available through other methods. In the part of experimental materials, we found many familiar compounds, such as 2-(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile(cas: 325141-71-7Name: 2-(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile)

2-(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile(cas: 325141-71-7) belongs to nitriles. Nitriles are found in many useful compounds. Nitrile rubber is also widely used as automotive and other seals since it is resistant to fuels and oils. Name: 2-(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile Industrially, the main methods for producing nitriles are ammoxidation and hydrocyanation. Both routes are green in the sense that they do not generate stoichiometric amounts of salts.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 50743-32-3On May 1, 1981 ,《Synthesis of 3-substituted-5-oxo-5H-[1]benzopyrano[2,3-b]pyridine derivatives》 appeared in Heterocycles. The author of the article were Ishiguro, Toshihiro; Ukawa, Kiyoshi; Sugihara, Hirosada; Nohara, Akira. The article conveys some information:

Oxobenzopyranopyridines I (R = H, 7-Me, 7-Et, 7-Me2CH, 7-Me3C, 7-Cl, 7-Me2CHO, 9-MeO, R1 = H; R = 7-Me, R1 = 9-Me; R2 = CN, CHO, alkoxycarbonyl) were prepared by cyclization reactions of the corresponding benzopyrancarboxaldehydes II with acetylenes or active methylene compounds Thus, cyclization of II (R = R1 = H) (III) with HCCCN or HCCCO2Et in DMF gave 32% I (R = R1 = H, R2 = CN) and 49% I (R = R1 = H, R2 = CO2Et), resp. Cyclocondensation of III with CH2[CH(OMe)2]2 in HCO2H containing F3B.OEt2 gave 10% I (R = R1 = H, R2 = CHO). I (R = H; R1 = 7-Et, 7-Me2CH; R2 = CN) were also prepared by hydrogenolysis of the corresponding 2-chloro derivatives of I (R2 = CN). In the part of experimental materials, we found many familiar compounds, such as 6-Isopropyl-4-oxo-4H-chromene-3-carbonitrile(cas: 50743-32-3Application of 50743-32-3)

6-Isopropyl-4-oxo-4H-chromene-3-carbonitrile(cas: 50743-32-3) belongs to nitriles. Nitriles are found in many useful compounds. Nitrile rubber is also widely used as automotive and other seals since it is resistant to fuels and oils. Application of 50743-32-3 Industrially, the main methods for producing nitriles are ammoxidation and hydrocyanation. Both routes are green in the sense that they do not generate stoichiometric amounts of salts.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Egami, Hiromichi; Hotta, Ryo; Otsubo, Minami; Rouno, Taiki; Niwa, Tomoki; Yamashita, Kenji; Hamashima, Yoshitaka published an article in Organic Letters. The title of the article was 《Asymmetric Dearomatizing Fluoroamidation of Indole Derivatives with Dianionic Phase-Transfer Catalyst》.COA of Formula: C10H7BrN2 The author mentioned the following in the article:

Asym. dearomatizing fluorocyclization of indole derivatives was investigated using a dicarboxylate phase-transfer catalyst. This reaction proceeded under mild reaction conditions to provide fluoropyrroloindoline derivatives I [R1 = H, 4-Me, 5-Cl, etc.; R2 = H, Me, Bn, etc.; R3 = SO2Me, 4-MeC6H4SO2, C6H5SO2] in a highly enantioselective manner. Various substitution patterns on the indole ring were well tolerated. To facilitate the reaction and ensure reproducibility, the addition of water was essential and its possible role was discussed. In the part of experimental materials, we found many familiar compounds, such as 2-(4-Bromo-3-indolyl)acetonitrile(cas: 89245-35-2COA of Formula: C10H7BrN2)

2-(4-Bromo-3-indolyl)acetonitrile(cas: 89245-35-2) is a member of nitriles. Nitriles have been reduced to amines by many methods, especially by catalytic hydrogenation and by metal hydrides. Aliphatic and aromatic nitriles have also been reduced to nitro derivatives using hydrazinium monoformate in the presence of Raney-nickel.COA of Formula: C10H7BrN2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2017,Garcia-Lopez, Victor; Alemany, Lawrence B.; Chiang, Pinn-Tsong; Sun, Jiuzhi; Chu, Pin-Lei; Marti, Angel A.; Tour, James M. published 《Synthesis of light-driven motorized nanocars for linear trajectories and their detailed NMR structural determination》.Tetrahedron published the findings.Formula: C7H3BrFN The information in the text is summarized as follows:

The design and synthesis of a fluorescent light-driven motorized nanocar with a linear geometry is described. Due to its structural design, the nanocar is present as a mixture of two photo-interconvertible diastereomers. An extensive and detailed NMR study allowed the full assignment of the chem. shifts of the two diastereomers in the mixture The nanocar is expected to translate in a linear motion due to the light-driven motor providing a paddle-wheel like propulsion. The quantum yield of 0.56 and the photostability of the dye make this nanocar suitable for future single-mol. fluorescence microscopy studies. In addition to this study using 4-Bromo-2-fluorobenzonitrile, there are many other studies that have used 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Formula: C7H3BrFN) was used in this study.

4-Bromo-2-fluorobenzonitrile(cas:105942-08-3) is used as a OLED intermediate, Pharmaceutical, electronic and chemical intermediate.Formula: C7H3BrFN It is used in the synthesis of heterocycles and liquid crystals.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2019,Chinese Chemical Letters included an article by Zhou, Chao; Diao, Pinhui; Li, Xiaoji; Ge, Yanqin; Guo, Cheng. Formula: C9H7NO. The article was titled 《Facile photochemical synthesis of α-ketoamides and quinoxalines from amines and benzoylacetonitrile under mild conditions》. The information in the text is summarized as follows:

A selective protocol for the synthesis of either α-ketoamides or quinoxaline derivatives under the same reaction conditions was achieved simply by varying substitution number of amino-groups. The method features metal-free, room temperature and broad substrate scope as well as no extra oxidant. This process applied to various substituent groups and provided products in moderate to good yield. Finally, a rational mechanism was proposed.3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Formula: C9H7NO) was used in this study.

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.Formula: C9H7NO

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2019,ACS Combinatorial Science included an article by Zhang, Mo; Chen, Meng-Nan; Li, Jiao-Mian; Liu, Nan; Zhang, Zhan-Hui. Recommanded Product: 3-Oxo-3-phenylpropanenitrile. The article was titled 《Visible-Light-Initiated One-Pot, Three-Component Synthesis of 2-Amino-4H-pyran-3,5-dicarbonitrile Derivatives》. The information in the text is summarized as follows:

A novel approach for the visible-light-initiated synthesis of 2-amino-4H-pyran-3,5-dicarbonitrile derivatives via a one-pot, three-component reaction of aldehydes or isatins, malononitrile, and α-cyano ketones was developed. The reaction was carried out at room temperature in ethanol/water to give the corresponding products with a wide range of functional groups in high yields. This process did not require any additives or chromatog. separation and could be applied for gram-scale synthesis. In the experiment, the researchers used many compounds, for example, 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Recommanded Product: 3-Oxo-3-phenylpropanenitrile)

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.Recommanded Product: 3-Oxo-3-phenylpropanenitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2019,Tetrahedron included an article by Balwe, Sandip Gangadhar; Kim, Jong Su; Kim, Yeong-Il; Jeong, Yeon Tae. Synthetic Route of C9H7NO. The article was titled 《Diversity-oriented one-pot synthesis of furan based densely substituted biheteroaryls via isocyanide insertion》. The information in the text is summarized as follows:

A facile and efficient acid-catalyzed cascade reaction for the synthesis of novel biheteroaryl structural motifs containing densely functionalized furans has been developed. The reaction sequence involves a Knoevenagel condensation of arylglyoxals with aroyl or heteroaroylacetonitrile and subsequently an isocyanide insertion via formal [4+1] cycloaddition followed by rapid [1,3]-H shift to afford uniquely decorated novel biheterocycles, e.g., I. Furthermore, the scope of the methodol. was extended to diverse biheteroaryls by employing 3-(2-furyl)-3-oxopropanenitrile, 3-cyanoacetyl-1-methylindole, 3-oxo-3-(1H-pyrrol-2-yl)propanenitrile, 3-(1H-indol-3-yl)-3-oxopropanenitrile, 3-oxo-3-(2-thienyl)propionitrile and benzoylacetonitriles. In addition to this study using 3-Oxo-3-phenylpropanenitrile, there are many other studies that have used 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Synthetic Route of C9H7NO) was used in this study.

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.Synthetic Route of C9H7NO

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2019,Organic Letters included an article by Janot, Christopher; Palamini, Pierre; Dobson, Benjamin C.; Muir, James; Aissa, Christophe. SDS of cas: 2042-37-7. The article was titled 《Palladium-Catalyzed Synthesis of Bis-Substituted Sulfoxonium Ylides》. The information in the text is summarized as follows:

α-Aryl-α-alkoxycarbonyl methylsulfoxonium ylides such as PhC-(CO2R)S+(:O)Me2 (R = Me, Et, Ph, Me3SiCH2CH2, t-BuMe2SiOCH2CH2OCH2CH2OCH2CH2) were prepared by palladium-catalyzed cross-coupling of α-sulfoxonium-substituted esters with aryl bromides and triflates and iodobenzene in the presence of either Pd(PPh3)4 or Pd2(dba)3 and t-Bu3P or XPhos. Sulfoxonium ylides were prepared from nicergoline and from the triflate ester of estrone. In the experiment, the researchers used many compounds, for example, 2-Bromobenzonitrile(cas: 2042-37-7SDS of cas: 2042-37-7)

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.SDS of cas: 2042-37-7

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2019,Chemical Science included an article by Donald, James R.; Berrell, Sophie L.. Synthetic Route of C8H6BrN. The article was titled 《Radical cyanomethylation via vinyl azide cascade-fragmentation》. The information in the text is summarized as follows:

A novel methodol. for radical cyanomethylation was described. The process was initiated by radical addition to the vinyl azide reagent 3-azido-2-methylbut-3-en-2-ol which triggered a cascade-fragmentation mechanism driven by the loss of dinitrogen and the stabilized 2-hydroxypropyl radical, ultimately effecting cyanomethylation. Cyanomethyl group was efficiently introduced into a range of substrates via trapping of α-carbonyl, heterobenzylic, alkyl, sulfonyl and aryl radicals, generated from a variety of functional groups under both photoredox catalysis and non-catalytic conditions. The value of this approach was exemplified by the late-stage cyanomethylation of pharmaceuticals. The experimental process involved the reaction of 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Synthetic Route of C8H6BrN)

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.Synthetic Route of C8H6BrN

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

《New Nanomagnetic Heterogeneous Cobalt Catalyst for the Synthesis of Aryl Nitriles and Biaryls》 was published in ACS Omega in 2020. These research results belong to Moghadam, Hadis Hosseini; Sobhani, Sara; Sansano, Jose Miguel. COA of Formula: C7H4FN The article mentions the following:

Cobalt nanoparticles immobilized on magnetic chitosan (Fe3O4@CS-Co) have been prepared They were identified using various techniques such as Fourier-transform IR spectroscopy, X-ray diffraction, field emission SEM, energy-dispersive X-ray spectroscopy, transmission electron microscopy, thermogravimetric anal., vibrating sample magnetometry, XPS, and inductively coupled plasma at. emission spectroscopy anal. and applied efficiently as a cobalt catalyst in the cyanation and fluoride-/palladium-free Hiyama reactions of different types of aryl halides ArX (Ar = Ph, 4-iodophenyl, pyridin-3-yl, etc.; X = I, Br, Cl) employing K4[Fe(CN)6].3H2O and triethoxyphenylsilane, resp. After each reaction, the catalyst was isolated and reused for the second run. The catalytic activity of the catalyst was not lost apparently even after five runs. No considerable changes in its chem. structure and morphol. were observed It is worth to note that in this paper, the cobalt catalyst has been used for the first time for the cyanation of aryl halides. In addition to this study using 4-Fluorobenzonitrile, there are many other studies that have used 4-Fluorobenzonitrile(cas: 1194-02-1COA of Formula: C7H4FN) was used in this study.

4-Fluorobenzonitrile(cas: 1194-02-1) is used in the synthesis of flurenones, pharmaceutical prerequisites, as well as opiod receptor antagonists.COA of Formula: C7H4FN

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts