Month: December 2022

A versatile cobalt catalyst for the reductive amination of carbonyl compounds with nitro compounds by transfer hydrogenation was written by Zhou, Peng;Zhang, Zehui;Jiang, Liang;Yu, Changlin;Lv, Kangle;Sun, Jie;Wang, Shuguo. And the article was included in Applied Catalysis, B: Environmental in 2017.Electric Literature of C14H12N2 This article mentions the following:

Co nanoparticles embedded in mesoporous nitrogen-doped carbon (abbreviated as Co@CN-800) were prepared and found to be resistant to acid. The Co@CN-800 catalyst was active and selective for the one-pot reductive amination of carbonyl compounds with nitro compounds by transfer hydrogenation with formic acid as the hydrogen donor, affording the corresponding secondary amines with excellent yields (89.6-99%). Both nitrogen atoms and Co nanoparticles were of great importance in the one-pot reductive amination over the Co@CN-800 catalyst by formic acid, and the protic N-H⁺ and hydridic Co-H^– were proposed to be the active species for the transfer hydrogenation reactions. Furthermore, the Co@CN-800 catalyst was highly stable without loss of its activity. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Electric Literature of C14H12N2).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) belongs to nitriles. Nitrile function is a very important functional group because it can be manipulated to other functional groups such as carboxylic acid by hydrolysis or amine by reduction, respectively. Some nitriles are manufactured by heating carboxylic acids with ammonia in the presence of catalysts. This process is used to make nitriles from natural fats and oils, the products being used as softening agents in synthetic rubbers, plastics, and textiles and for making amines.Electric Literature of C14H12N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Condensation of 3-methyl-6-nitrobenzonitrile and 3-methyl-6-nitrobenzamide with benzaldehyde was written by Macovski, Eugen;Georgescu, Julia. And the article was included in Bulletin de la Section Scientifique de l’ Academie Roumaine in 1946.HPLC of Formula: 64113-86-6 This article mentions the following:

Nitration of m-MeC₆H₄CN gives a mixture of 3-methyl-6-nitrobenzonitrile (I), m. 92°, and isomeric nitro compounds removable by steam distillation The distillate with KOH-H₂O₂ gives 3-methyl-2-nitrobenzamide (II), m. 192°, and 3-methyl-5-nitrobenzamide (III), m. 166°. Heating II with BzH 2 hrs. at 160° gives N,N’-benzylidenebis(3-methyl-2-nitrobenzamide), m. 243°; III gives N,N’-benzylidenebis(3-methyl-5-nitrobenzamide), m. 235-7°. I with KOH-H₂O₂ gives 3-methyl-6-nitrobenzamide (IV), m. 176-7°, not hydrolyzed by alc. NaOMe at 37°. BzH converts IV into N,N’-benzylidenebis(3-methyl-6-nitrobenzamide), m. 263°. IV with BzH in the presence of piperidine at 160° gives 3-carbamyl-4-nitrostilbene (V), m. 241°; hydrolysis of 3-cyano-4-nitrostilbene by KOH-H₂O₂ and condensation of IV with BzH in the presence of NaOEt at 37° also give V. In the experiment, the researchers used many compounds, for example, 5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6HPLC of Formula: 64113-86-6).

5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6) belongs to nitriles. There has been no report on the microbial biosynthesis of nitriles and the physiological function of such enzymes, nor was it not even known whether aliphatic and aromatic nitriles are biological compounds or just petrochemicals. Alkyl nitriles are sufficiently acidic to undergo deprotonation of the C-H bond adjacent to the CN group.Strong bases are required, such as lithium diisopropylamide and butyl lithium. The product is referred to as a nitrile anion. HPLC of Formula: 64113-86-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis, reactions, and antimicrobial activity of some fused thieno[2,3-d]yrimidine derivatives was written by Prabhu, Pradnya J.;Khombare, Rajiv T.;Kadam, Mangesh D.. And the article was included in International Journal of Chemistry (Mumbai, India) in 2013.Safety of Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate This article mentions the following:

Novel thieno[2,3-d]pyrimidines, 4-imino-pyrimidin-3-ylamine and pyrimidon-4-ylhydrazine derivatives were prepared starting from ethyl-5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate and 5-amino-4-cyano-3-methyl-thiophene-2-carboxylic acid Et ester. The antimicrobial evaluation of the synthesized compounds showed that many of them revealed promising antimicrobial activity. In the experiment, the researchers used many compounds, for example, Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate (cas: 58168-20-0Safety of Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate).

Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate (cas: 58168-20-0) belongs to nitriles. The electronic structure of nitriles is very similar to that of an alkyne with the main difference being the presence of a set of lone pair electrons on the nitrogen. 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.Safety of Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis of benzylidenemalononitrile by Knoevenagel condensation through monodisperse carbon nanotube-based NiCu nanohybrids was written by Zengin, Nursefa;Burhan, Hakan;Savk, Aysun;Goksu, Haydar;Sen, Fatih. And the article was included in Scientific Reports in 2020.Name: 2-(Anthracen-9-ylmethylene)malononitrile This article mentions the following:

Monodisperse nickel/copper nanohybrids (NiCu@MWCNT) based on multi-walled carbon nanotubes (MWCNT) were prepared for the Knoevenagel condensation of aryl and aliphatic aldehydes. The synthesis of these nanohybrids was carried out by the ultrasonic hydroxide assisted reduction method. NiCu@MWCNT nanohybrids were characterized by anal. techniques such as X-ray diffraction (XRD), XPS, transmission electron microscopy (TEM), high-resolution transmission electron microscopy (HR-TEM), and Raman spectroscopy. According to characterization results, NiCu@MWCNT showed that these nanohybrids form highly uniform, crystalline, monodisperse, colloidally stable NiCu@MWCNT nanohybrids were successfully synthesized. Thereafter, a model reaction was carried out to obtain benzylidenemalononitrile derivatives using NiCu@MWCNT as a catalyst, and showed high catalytic performance under mild conditions over 10-180 min. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Name: 2-(Anthracen-9-ylmethylene)malononitrile).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. Nitrile groups in organic compounds can undergo a variety of reactions depending on the reactants or conditions. A nitrile group can be hydrolyzed, reduced, or ejected from a molecule as a cyanide ion.Name: 2-(Anthracen-9-ylmethylene)malononitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Hypervalent Iodine(III)-Catalyzed Epoxidation of β-Cyanostyrenes was written by Mangaonkar, Saeesh R.;Singh, Fateh V.. And the article was included in Synthesis in 2019.Computed Properties of C18H10N2 This article mentions the following:

A convenient approach for the synthesis of β-cyanoepoxides is illustrated by iodine(III)-catalyzed epoxidation of electron-deficient β-cyanostyrenes, wherein the active catalytic iodine(III) species was generated in situ. The epoxidation of β-cyanostyrenes was performed using 10 mol% PhI as precatalyst in the presence of 2.0 equiv oxone as an oxidant and 2.4 equiv of TFA as an additive at room temperature under ultrasonic radiations. The β-cyanoepoxides were isolated in good to excellent yields in a short reaction time. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Computed Properties of C18H10N2).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) belongs to nitriles. There has been no report on the microbial biosynthesis of nitriles and the physiological function of such enzymes, nor was it not even known whether aliphatic and aromatic nitriles are biological compounds or just petrochemicals. In conventional organic reductions, nitrile is reduced by treatment with lithium aluminium hydride to the amine. Reduction to the imine followed by hydrolysis to the aldehyde takes place in the Stephen aldehyde synthesis, which uses stannous chloride in acid.Computed Properties of C18H10N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Formal Substitution of Bromocyclopropanes with Nitrogen Nucleophiles was written by Banning, Joseph E.;Gentillon, Jacob;Ryabchuk, Pavel G.;Prosser, Anthony R.;Rogers, Andrew;Edwards, Andrew;Holtzen, Andrew;Babkov, Ivan A.;Rubina, Marina;Rubin, Michael. And the article was included in Journal of Organic Chemistry in 2013.Recommanded Product: 10282-32-3 This article mentions the following:

A highly chemo- and diastereoselective protocol toward amino-substituted donor-acceptor cyclopropanes via the formal nucleophilic displacement in bromocyclopropanes is described. A wide range of N-nucleophiles, including carboxamides, sulfonamides, azoles, and anilines, can be efficiently employed in this transformation, providing expeditious access to stereochem. defined and densely functionalized cyclopropylamine derivatives In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Recommanded Product: 10282-32-3).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) belongs to nitriles. The R-C-N bond angle in and nitrile is 180° which give a nitrile functional group a linear shape. Both the carbon and the nitrogen are sp hydridized which leaves them both with two p orbitals which overlap to form the two π bond in the triple bond. Nitriles are susceptible to hydrogenation over diverse metal catalysts. The reaction can afford either the primary amine (RCH2NH2) or the tertiary amine ((RCH2)3N), depending on conditions.Recommanded Product: 10282-32-3

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Nonlinear optical properties of retinal derivatives was written by Ikeda, Hidetsugu;Kawabe, Yutaka;Sakai, Toshio;Kawasaki, Kenji. And the article was included in Chemistry Letters in 1989.Synthetic Route of C18H10N2 This article mentions the following:

Retinal derivatives I [Z = C(CN)C₆H₄NO₂–p, C(CN)₂, NC₆H₄NMe₂–p] with electron donors or acceptors were synthesized and their 2nd order nonlinear optical properties were investigated by elec. field induced 2nd harmonic generation (EFISH) method. Retinal derivatives were found to have large 2nd order optical nonlinearities. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Synthetic Route of C18H10N2).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Synthetic Route of C18H10N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis of macrobicyclic polyamines by direct macrobicyclization via tripode-tripode coupling was written by Dietrich, Bernard;Hosseini, Mir Wais;Lehn, Jean Marie;Sessions, Richard B.. And the article was included in Helvetica Chimica Acta in 1985.Reference of 7528-78-1 This article mentions the following:

Five macrobicyclic polyamines, e.g., I, were prepared by a coupling reaction involving two tripodal subunits. The key macrobicyclization steps involve condensation of a tris-terminal tosylamine tripodal subunit with a tris-terminal tripodal mesylate. Thus, Michael addition of Me acrylate with N(CH₂CH₂CH₂NHTs)₃ (II; Ts = tosyl) gave the triester, which was reduced and mesylated to give N(CH₂CH₂CH₂NTsCH₂CH₂CH₂OMs)₃ (III; Ms = mesyl). Tripode III was condensed with tripode II at 95° in DMF in the presence of Cs₂CO₃ to give the macrobicyclic hexatosylamine in 50% yield. The last was detosylated with PhOH in HBr/AcOH to give I as the HBr salt. In the experiment, the researchers used many compounds, for example, 3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1Reference of 7528-78-1).

3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. Some nitriles are manufactured by heating carboxylic acids with ammonia in the presence of catalysts. This process is used to make nitriles from natural fats and oils, the products being used as softening agents in synthetic rubbers, plastics, and textiles and for making amines.Reference of 7528-78-1

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Varying the ratio of formic acid to triethylamine impacts on asymmetric transfer hydrogenation of ketones was written by Zhou, Xiaowei;Wu, Xiaofeng;Yang, Bolun;Xiao, Jianliang. And the article was included in Journal of Molecular Catalysis A: Chemical in 2012.Name: (R)-4-(1-Hydroxyethyl)benzonitrile This article mentions the following:

Asym. transfer hydrogenation (ATH) is frequently carried out in the azeotropic mixture of formic acid (F) and triethylamine (T), where the F/T molar ratio is 2.5. This study shows that the F/T ratio affects both the reduction rate and enantioselectivity, with the optimum ratio being 0.2 in the ATH of ketones with the Ru-TsDPEN catalyst. Under such conditions, a range of substrates have been reduced, affording high yields and good to excellent enantioselectivities. In comparison with the common azeotropic F-T system, the reduction is faster. This protocol improves both the classic azeotropic and the aqueous-formate system when using water-insoluble ketones. In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6Name: (R)-4-(1-Hydroxyethyl)benzonitrile).

(R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6) belongs to nitriles. Nitrile compounds can be prepared by the incorporation of a cyanide source through C–C bond formation or by dehydration of primary carboxamides. Some nitriles are manufactured by heating carboxylic acids with ammonia in the presence of catalysts. This process is used to make nitriles from natural fats and oils, the products being used as softening agents in synthetic rubbers, plastics, and textiles and for making amines.Name: (R)-4-(1-Hydroxyethyl)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Remarkably stable (Me₃Al)₂·DABCO and stereoselective nickel-catalyzed AlR₃ (R = Me, Et) additions to aldehydes was written by Biswas, Kallolmay;Prieto, Oscar;Goldsmith, Paul J.;Woodward, Simon. And the article was included in Angewandte Chemie, International Edition in 2005.Computed Properties of C9H9NO This article mentions the following:

Chiral nonracemic secondary alcs. are prepared by the addition of either bis(trialkylaluminum) adducts of DABCO or trialkylaluminum reagents to aldehydes in the presence of Ni(acac)₂ and the Feringa binaphthyl phosphoramidite ligand derived from (R)-BINOL and (S,S)-N,N-bis(1-phenylethyl)amine. In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6Computed Properties of C9H9NO).

(R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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.Computed Properties of C9H9NO

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts