Month: October 2022

Synthetic Route of C43H30F2N4On November 14, 2018 ,《A Toolbox Approach To Construct Broadly Applicable Metal-Free Catalysts for Photoredox Chemistry: Deliberate Tuning of Redox Potentials and Importance of Halogens in Donor-Acceptor Cyanoarenes》 appeared in Journal of the American Chemical Society. The author of the article were Speckmeier, Elisabeth; Fischer, Tillmann G.; Zeitler, Kirsten. The article conveys some information:

The targeted choice of specific photocatalysts has been shown to play a critical role for the successful realization of challenging photoredox catalytic transformations. Herein, we demonstrate the successful implementation of a rational design strategy for a series of deliberate structural manipulations of cyanoarene-based, purely organic donor-acceptor photocatalysts, using 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN) as a starting point. Systematic modifications of both the donor substituents as well as the acceptors’ mol. core allowed us to identify strongly oxidizing as well as strongly reducing catalysts (e.g., for an unprecedented detriflation of unactivated naphthol triflate), which addnl. offer remarkably balanced redox potentials with predictable trends. Especially halogen arene core substitutions are instrumental for our targeted alterations of the catalysts’ redox properties. Based on their preeminent electrochem. and photophys. characteristics, all novel, purely organic photoredox catalysts were evaluated in three challenging, mechanistically distinct classes of benchmark reactions (either requiring balanced, highly oxidizing or strongly reducing properties) to demonstrate their enormous potential as customizable photocatalysts, that outperform and complement prevailing typical best photocatalysts. In the experiment, the researchers used 2,4,6-Tris(diphenylamino)-3,5-difluorobenzonitrile(cas: 1403850-00-9Synthetic Route of C43H30F2N4)

2,4,6-Tris(diphenylamino)-3,5-difluorobenzonitrile(cas: 1403850-00-9) is cyanoarene-based donor-acceptor photocatalyst developed by the Zeitler group. While this catalyst has a balanced redox profile, allowing for its use in a variety of transformations, it stands out as the most reducing catalyst of the family.Synthetic Route of C43H30F2N4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The author of 《Dissociation of naphthoic acids in non-aqueous media. Comparison of benzene and naphthalene skeletons》 were Parik, Patrik; Wolfova, Jitka; Ludwig, Miroslav. And the article was published in Collection of Czechoslovak Chemical Communications in 2000. Application In Synthesis of 5-Amino-1-naphthonitrile The author mentioned the following in the article:

Seven monosubstituted 1-naphthoic acids were synthesized by new or modified procedures, and their dissociation constants were measured potentiometrically at 25° in MeOH, MeCN, DMF, and pyridine. Dissociation constants of these along with 13 substituted 1-naphthoic acids and twenty-five substituted 2-naphthoic acids previously studied were measured at 25° in EtOH and DMSO. The pKKA values of 3- and 4-substituted 1-naphthoic acids were treated by simple linear regression and principal component anal., and the results were used for comparison of model compounds and of corresponding 3- and 4-substituted benzoic acids with the aim of comparison of benzene and naphthalene skeletons. It was found, the 3 and 4 positions of the 1-naphthyl system can roughly be compared with the meta and para positions of benzene, resp. The experimental part of the paper was very detailed, including the reaction process of 5-Amino-1-naphthonitrile(cas: 72016-73-0Application In Synthesis of 5-Amino-1-naphthonitrile)

5-Amino-1-naphthonitrile(cas: 72016-73-0) belongs to anime. Halogenation, in which one or more hydrogen atoms of an amine is replaced by a halogen atom, occurs with chlorine, bromine, and iodine, as well as with some other reagents, notably hypochlorous acid (HClO). With primary amines the reaction proceeds in two stages, producing N-chloro- and N,N-dichloro-amines, RNHCl and RNCl2, respectively. With tertiary amines, an alkyl group may be displaced by a halogen.Application In Synthesis of 5-Amino-1-naphthonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2007,Paillet-Loilier, Magalie; Fabis, Frederic; Lepailleur, Alban; Bureau, Ronan; Butt-Gueulle, Sabrina; Dauphin, Francois; Lesnard, Aurelien; Delarue, Catherine; Vaudry, Hubert; Rault, Sylvain published 《Novel aminoethylbiphenyls as 5-HT7 receptor ligands》.Bioorganic & Medicinal Chemistry Letters published the findings.Product Details of 31938-07-5 The information in the text is summarized as follows:

The synthesis of a series of aminoethylbiphenyls, e.g., I, as novel 5-HT7 receptor ligands is described. The novel derivatives exhibit high affinity for the 5-HT7 receptor with selectivity toward 5-HT1A receptor. In the experiment, the researchers used many compounds, for example, 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Product Details of 31938-07-5)

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.Product Details of 31938-07-5

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

《Organophotoredox assisted cyanation of bromoarenes via silyl-radical-mediated bromine abstraction》 was written by Shee, Maniklal; Shah, Sk. Sheriff; Singh, N. D. Pradeep. Synthetic Route of C7H4FN And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2020. The article conveys some information:

The insertion of a nitrile (-CN) group into arenes through the direct functionalization of the C(sp2)-Br bond is a challenging reaction. Herein, we report an organophotoredox method for the cyanation of aryl bromides using the organic photoredox catalyst 4CzIPN (1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene) and tosyl cyanide (TsCN) as the nitrile source. A photogenerated silyl radical, via a single electron transfer (SET) mechanism, was employed to abstract bromine from aryl bromide to provide an aryl radical, which was concomitantly intercepted by TsCN to afford the aromatic nitrile. A range of substrates containing electron-donating and -withdrawing groups was demonstrated to undergo cyanation at room temperature in good yields. Thus, e.g., Me 4-bromobenzoate → Me 4-cyanobenzoate (71%) employing 4CzIPN, TsCN, (TMS)3SiOH as silyl radical source, K3PO4 as base, acetone as solvent and irradiation from blue LED. The experimental part of the paper was very detailed, including the reaction process of 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

Yang, Ren-Yin; Wang, Hui; Xu, Bo published their research in Chemical Communications (Cambridge, United Kingdom) in 2021. The article was titled 《Base promoted gem-difluoroolefination of alkyl triflones》.Recommanded Product: 4-Cyanobenzyl bromide The article contains the following contents:

A new synthesis of gem-difluoroalkenes ArC(R)=CF2 [Ar = 4-bromophenyl, naphthalen-2-yl, 5-(methoxycarbonyl)thiophen-2-yl, etc.; R = prop-2-en-1-yl, 3-phenylprop-2-yn-1-yl, (4-methylphenyl)methyl, etc.] from readily available alkyl triflones ArCH(R)S(O)2CF3 and difluorocarbene precursors such as TMSCF2Br has been reported. The reaction, regardless of electronic effect, gives gem-difluoroalkenes ArC(R)=CF2 in good to excellent yields. The mechanism may involve deprotonation of triflones, nucleophilic addition, and the elimination of SO2CF3. In the experiment, the researchers used 4-Cyanobenzyl bromide(cas: 17201-43-3Recommanded Product: 4-Cyanobenzyl bromide)

4-Cyanobenzyl bromide(cas: 17201-43-3) is a white solid. Its melting point is 113-117°C, and flash point is 125.1°C. It is insoluble in water at 20°C. It is stable under normal temperatures and pressures. It should be stored at 0-5°C.Recommanded Product: 4-Cyanobenzyl bromide

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Computed Properties of C8H6BrNIn 2019 ,《Self-assembly of a “”cationic-cage”” via the formation of Ag-carbene bonds followed by imine condensation》 was published in Chemical Communications (Cambridge, United Kingdom). The article was written by Modak, Ritwik; Mondal, Bijnaneswar; Howlader, Prodip; Mukherjee, Partha Sarathi. The article contains the following contents:

A new strategy for the synthesis of a “”cationic-cage”” (CC-Ag) has been developed via metal-carbene (M-CNHC) bond formation followed by imine bond condensation. Reaction of a trigonal trisimidazolium salt H3L(PF6)3 functionalized with three flexible N-phenyl-aldehyde pendants with silver oxide yielded a trinuclear tricationic organometallic cage (OC-Ag). Subsequent treatment of the organometallic cage (OC-Ag) with 1,4-diaminobutane links the two tris-NHC ligands via imine bond condensation, which thus generates a 3D ‘cationic-cage’ (CC-Ag). Furthermore, post-synthetic replacement of the Ag(I) with Au(I) leading to the formation of CC-Au was achieved via trans-metalation, with the retention of the mol. architecture. In the experiment, the researchers used many compounds, for example, 4-Cyanobenzyl bromide(cas: 17201-43-3Computed Properties of C8H6BrN)

4-Cyanobenzyl bromide(cas: 17201-43-3) can reacts with 2H-tetrazole in the presence of KOH to yield 4-[(2H-tetra-zol-2-yl)methyl]benzonitrile. And it may be used in the synthesis of ligands containing a chelating pyrazolyl-pyridine group with a pendant aromatic nitrile.Computed Properties of C8H6BrN

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2014,Mentese, Emre; Bektas, Hakan; Uelker, Serdar; Bekircan, Olcay; Kahveci, Bahittin published 《Microwave-assisted synthesis of new benzimidazole derivatives with lipase inhibition activity》.Journal of Enzyme Inhibition and Medicinal Chemistry published the findings.Product Details of 31938-07-5 The information in the text is summarized as follows:

A practical protocol was used for the synthesis of benzimidazoles. The reaction of Et phenylacetimidate hydrochlorides with 4,5-dichloro-1,2-phenylenediamine under microwave irradiation leads to the benzimidazole derivatives with good yields and in short reaction times. The corresponding ester and hydrazide derivatives were synthesized subsequently under microwave irradiation with good yields. All compounds were evaluated with regard to pancreatic lipase activity and benzimidazoles I (R = H, R1 = Br; R = Br, R1 = H) and II (R = H, CH2CO2Me) showed lipase inhibition at various concentrations2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Product Details of 31938-07-5) was used in this study.

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.Product Details of 31938-07-5

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

《Two-step gas adsorption induced by the transmetalation in a two-dimensional metal-organic framework》 was published in Chemical Communications (Cambridge, United Kingdom) in 2020. These research results belong to Park, Hye Jeong; Oh, Jongbum; Kim, Jiwon; Kim, Jaheon. Related Products of 1194-02-1 The article mentions the following:

Transmetalation or replacement of Zn2+ ions with Cu2+ ions in a two-dimensional metal-organic framework, Zn3(TCPB)2(H2O)2 (H3TCPB = 1,3,5-tri(4-carboxyphenoxy)benzene), gives rise to addnl. gas adsorption, where the addnl. adsorption amount linearly depends on the degree of the transmetalation. The experimental process involved the reaction of 4-Fluorobenzonitrile(cas: 1194-02-1Related Products of 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.Related Products of 1194-02-1

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

《Scope and mechanism of nitrile dihydroboration mediated by a β-diketiminate manganese hydride catalyst》 was written by Nguyen, Thao T.; Kim, Jun-Hyeong; Kim, Suyeon; Oh, Changjin; Flores, Marco; Groy, Thomas L.; Baik, Mu-Hyun; Trovitch, Ryan J.. Recommanded Product: 4-Fluorobenzonitrile And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2020. The article conveys some information:

The Manganese hydride dimer, [(2,6-iPr2PhBDI)Mn(μ-H)]2, was found to mediate nitrile dihydroboration, rendering it the 1st Mn catalyst for this transformation. Stoichiometric experiments revealed that benzonitrile insertion affords [(2,6-iPr2PhBDI)Mn(μ-NCHC6H5)]2 en route to N,N-diborylamine formation. D. functional theory calculations reveal the precise mechanism and demonstrate that catalysis is promoted by monomeric species. In the part of experimental materials, we found many familiar compounds, such as 4-Fluorobenzonitrile(cas: 1194-02-1Recommanded Product: 4-Fluorobenzonitrile)

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: 4-Fluorobenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reddy, G. Jagath; Latha, D.; Thirupathaiah, C.; Rao, K. Srinivasa published an article in Organic Preparations and Procedures International. The title of the article was 《An efficient one step conversion of 3-formylchromones into 3-cyanochromones》.Recommanded Product: 6-Isopropyl-4-oxo-4H-chromene-3-carbonitrile The author mentioned the following in the article:

A one step conversion of 3-formylchromones into 3-cyanochromones. Substituted 3-formylchromones were heated with hydroxylamine hydrochloride in refluxing acetonitrile in the presence of sodium iodide to give 3-cyanochromones in good yields. The results came from multiple reactions, including the reaction of 6-Isopropyl-4-oxo-4H-chromene-3-carbonitrile(cas: 50743-32-3Recommanded Product: 6-Isopropyl-4-oxo-4H-chromene-3-carbonitrile)

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. Organic compounds containing multiple nitrile groups are known as cyanocarbons.Recommanded Product: 6-Isopropyl-4-oxo-4H-chromene-3-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts