Category: nitriles-buliding-blocks

Well-Defined Phosphine-Free Iron-Catalyzed N-Ethylation and N-Methylation of Amines with Ethanol and Methanol was written by Lator, Alexis;Gaillard, Sylvain;Poater, Albert;Renaud, Jean-Luc. And the article was included in Organic Letters in 2018.Product Details of 4714-63-0 This article mentions the following:

An iron(0) complex bearing a cyclopentadienone ligand catalyzed N-methylation and N-ethylation of aryl and aliphatic amines with methanol or ethanol in mild and basic conditions through a hydrogen autotransfer borrowing process is reported. A broad range of aromatic and aliphatic amines underwent mono- or dimethylation in high yields. DFT calculations suggest mol. hydrogen acts not only as a reducing agent but also as an additive to displace thermodn. equilibrium In the experiment, the researchers used many compounds, for example, 4-(Ethylamino)benzonitrile (cas: 4714-63-0Product Details of 4714-63-0).

4-(Ethylamino)benzonitrile (cas: 4714-63-0) 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. 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.Product Details of 4714-63-0

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Design, Synthesis, and Biological Activity of 4-[(4-Cyano-2-arylbenzyloxy)-(3-methyl-3H-imidazol-4-yl)methyl]benzonitriles as Potent and Selective Farnesyltransferase(FTase) Inhibitors was written by Wang, Le;Wang, Gary T.;Wang, Xilu;Tong, Yunsong;Sullivan, Gerry;Park, David;Leonard, Nicholas M.;Li, Qun;Cohen, Jerry;Gu, Wen-Zhen;Zhang, Haiying;Bauch, Joy L.;Jakob, Clarissa G.;Hutchins, Charles W.;Stoll, Vincent S.;Marsh, Kennan;Rosenberg, Saul H.;Sham, Hing L.;Lin, Nan-Horng. And the article was included in Journal of Medicinal Chemistry in 2004.Formula: C8H8N2 This article mentions the following:

A novel series of 4-[(4-cyano-2-arylbenzyloxy)-(3-methyl-3H-imidazol-4-yl)methyl]benzonitriles have been synthesized as selective farnesyltransferase inhibitors using a structure-based design. X-ray cocrystal structures of compound 6-[[(1R)-(4-cyanophenyl)(1-methyl-1H-imidazol-5-yl)methoxy]methyl]-3′-methoxy[1,1′-biphenyl]-3-carbonitrile-FTase-HFP and A313326-FTase-HFP confirmed our initial design. The decreased interaction between the aryl groups and Ser 48 in GGTase-I binding site could be one possible reason to explain the improved selectivity for this new series of FTase inhibitors. Medicinal chem. efforts led to the discovery of 3-cyano-6-[[(4-cyanophenyl)(1-methyl-1H-imidazol-5-yl)methoxy]methyl]-N-phenylbenzamide (I) with potent cellular activity (EC₅₀ = 3.5 nM) and outstanding pharmacokinetic profiles in dog (96% bioavailable, 18.4 h oral t_1/2, and 0.19 L/(h·kg) plasma clearance). In the experiment, the researchers used many compounds, for example, 3-Amino-4-methylbenzonitrile (cas: 60710-80-7Formula: C8H8N2).

3-Amino-4-methylbenzonitrile (cas: 60710-80-7) 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. 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.Formula: C8H8N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Rhodium-Catalyzed Pyridine N-Oxide Assisted Suzuki-Miyaura Coupling Reaction via C(O)-C Bond Activation was written by Zhong, Jing;Long, Yang;Yan, Xufei;He, Shiyu;Ye, Runyou;Xiang, Haifeng;Zhou, Xiangge. And the article was included in Organic Letters in 2019.Application of 36057-44-0 This article mentions the following:

A rhodium-catalyzed Suzuki-Miyaura coupling reaction via C(O)-C bond activation to form 2-benzoylpyridine N-oxide derivatives is reported. Both the C(O)-C(sp²) and C(O)-C(sp³) bond could be activated during the reaction with yields up to 92%. The N-oxide moiety could be employed as a traceless directing group, leading to free pyridine ketones. In the experiment, the researchers used many compounds, for example, 4-methoxypicolinonitrile (cas: 36057-44-0Application of 36057-44-0).

4-methoxypicolinonitrile (cas: 36057-44-0) 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. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Application of 36057-44-0

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Syntheses with acrylonitrile. IX. Reaction of acrylonitrile with ammonia and preparation of trimethylenediamine was written by Terent’ev, A. P.;Chursina, K. I.;Kost, A. N.. And the article was included in Zhurnal Obshchei Khimii in 1950.Safety of 3,3′,3”-Nitrilotripropanenitrile This article mentions the following:

Reaction of CH₂:CHCN (I) with NH₃ involves consecutive equilibrium with H₂NCH₂CH₂CN, HN(CH₂CH₂CN)₂, and N(CH₂CH₂CN)₃. Slow addition of 95 g. I to 950 ml. 32% NH₄OH with cooling 2 hrs. below 35° and stirring 30 min. gave 30% β-aminopropionitrile and 47.2% β, β’-iminodipropionitrile, and a small amount of the trisubstitution product. Decrease of the amount of NH₄OH lowers the primary product yield, but if the concentration of the mixture is done in an NH₃ stream the yield rises to 34-6%. H₂NCH₂CH₂CN, b₁₄ 77-8°, b₁₈ 84-6°, b₂₃ 89°, n_D²⁰ 1.4390, d₄²⁰ 0.9584 [HCl salt, m. 163-3.5° (from EtOH)]; HN(CH₂CH₂CN)₂, b₁₄ 177-9 °, b₂₂ 209-11°, n_D²⁰ 1.4630, d₄²⁰ 1.0196 [HCl salt, m. 147-8° (from MeOH), gives with BzCl in C₆H₆ BzN(CH₂CH₂CN)₂, m. 112° (from MeOH); PhSO₂Cl gave the PhSO₂ analog, m. 88° (from MeOH)]. Heating 6.2 g. HN(CH₂CH₂CN)₂ and 8 g. I in an ampul 60 hrs. at 160-80° gave 40% N(CH₂CH₂CN)₃, m. 57-8° (from EtOH-Et₂O-H₂O). Addition of 14 g. H₂NCH₂CH₂CN in 450 ml. BuOH to 30 g. Na-K alloy (2% K) and rapid heating gave, after the usual steam distillation from acidified solution, 81% trimethylenediamine-HCl, m. 242° (from EtOH); use of old nitrile or of iso-AmOH gave lower yields; free base, readily obtained in 74% yield from the HCl salt with NaOH and Et₂O, b₇₅₆ 136-8°, b₇₃₅ 134-6°, n_D²⁰ 1.4590, d₄²⁰ 0.8834 (dried over Na before distillation); BaO or Na₂O gave lower yields. Similar reduction of HN(CH₂CH₂CN)₂ in BuOH gave 22-5% HN(CH₂CH₂CH₂NH₂)₂, b_5-6 105-6°, b₉ 108°, b₁₇ 114-17°, n_D²⁰ 1.4846, d₄²⁰ 0.9386; HCl salt, decompose 259° (from aqueous MeOH); tripicrate, decompose 226-7° (from H₂O). In the experiment, the researchers used many compounds, for example, 3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1Safety of 3,3′,3”-Nitrilotripropanenitrile).

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. 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.Safety of 3,3′,3”-Nitrilotripropanenitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Palladium-Catalyzed Amination of Aryl Nonaflates was written by Anderson, Kevin W.;Mendez-Perez, Maria;Priego, Julian;Buchwald, Stephen L.. And the article was included in Journal of Organic Chemistry in 2003.HPLC of Formula: 10282-32-3 This article mentions the following:

The first detailed study of the palladium-catalyzed amination of aryl nonaflates is reported. Use of ligands such as BINAP allows for the catalytic amination of electron-rich and -neutral aryl nonaflates with both primary and secondary amines. With use of Xantphos, the catalytic amination of a variety of functionalized aryl nonaflates resulted in excellent yields of anilines; even 2-carboxymethyl aryl nonaflate is effectively coupled with a primary alkylamine. Moderate yields were obtained when coupling halo-aryl nonaflates with a variety of amines, where in most cases the aryl nonaflate reacted in preference to the aryl halide. Overall, aryl nonaflates are an effective alternative to triflates in palladium-catalyzed C-N bond-forming processes due to their increased stability under the reaction conditions. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3HPLC of Formula: 10282-32-3).

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. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.HPLC of Formula: 10282-32-3

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Polarographic behavior of thiophene 5- and 4-nitro derivatives was written by Freidlin, G. N.;Glushkova, A. A.;Solop, K. A.. And the article was included in Zhurnal Analiticheskoi Khimii in 1979.Name: 4-Nitrothiophene-2-carbonitrile This article mentions the following:

The polarog. behavior of 20 2-substituted 4- and 5-nitrothiophene derivatives was examined A method is described for the simultaneous determination of isomers in binary and ternary systems in the 1 × 10^-5-2 × 10^-4 mol/L range. The derivatives can be presented as 2 series, which are described by Hammett equations for the E_1/2 values. Best results are obtained during the polarog. determination of nitration products by using acetate buffer solution (pH 3.7) and 40% EtOH. The standard deviation is 2-8%. In the experiment, the researchers used many compounds, for example, 4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6Name: 4-Nitrothiophene-2-carbonitrile).

4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6) 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. 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.Name: 4-Nitrothiophene-2-carbonitrile

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reactions of N-aminopyridinium derivatives. XII. Nucleophilic reactions of N-aminopyridinium derivatives was written by Ohsawa, Akio;Hirobe, Masaaki;Okamoto, Toshihiko. And the article was included in Yakugaku Zasshi in 1972.Synthetic Route of C7H6N2O This article mentions the following:

Derivatives of N-aminopyridine were synthesized and these derivatives underwent reaction with nucleophilic reagents. Progress of this reaction depended on the activity of the reagents as a nucleophilic species, substituent effect of the substrate, and reaction conditions. Electron-withdrawing nature of the substituent on the amino group determines the activity of the substrate while that of the substituent on ring C determines the orientation of the reaction, the greater the electron-withdrawing nature of ring C the greater the orientation towards the 2-position. The reaction results in addition and (or) substitution reaction and the reaction can be explained without inconsistency by assuming the progress of this reaction in 2 steps of addition and liberation even when only a substitution product is obtained. Depending on whether the addition step is reversible or irreversible, each step will be controlled either by thermokinetics or by chem. kinetics, and orientation towards the 4- or 2-position will be determined by which of these forces would be stronger. In the experiment, the researchers used many compounds, for example, 4-methoxypicolinonitrile (cas: 36057-44-0Synthetic Route of C7H6N2O).

4-methoxypicolinonitrile (cas: 36057-44-0) 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 addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Synthetic Route of C7H6N2O

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Flexible covalent tripods in nonadentate podands: synthesis of tris[3-(6-diethylcarbamoylpyridine-2-carboxamido)propyl]amine and its complexing properties with trivalent lanthanides was written by Renaud, Fabien;Decurnex, Carole;Piguet, Claude;Hopfgartner, Gerard. And the article was included in Journal of the Chemical Society, Dalton Transactions in 2001.Electric Literature of C9H12N4 This article mentions the following:

The nonadentate podand tris[3-(6-diethylcarbamoylpyridine-2-carboxamido)propyl]amine (L¹⁴) is prepared according to a multistep strategy using the flexible tris(3-(N-methylamino)propyl)amine (Me-TRPN) covalent tripod. L¹⁴ exists as a statistical mixture of four conformers in solution whose distribution is slightly affected by protonation of the apical nitrogen atom in [L¹⁴ + H]⁺. Reactions of L¹⁴ and [L¹⁴ + H]⁺ with Ln³⁺ (Ln = La-Lu) produce flexible and poorly stable 1:1 podates [Ln(L¹⁴)]³⁺ and [Ln(L¹⁴ + H)]⁴⁺ in which the terdentate chelating binding units exhibit partial dynamic on-off complexation equilibrium In the experiment, the researchers used many compounds, for example, 3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1Electric Literature of C9H12N4).

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. 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.Electric Literature of C9H12N4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A simplified method to prepare 2-amino-5-bromopyrimidine. A laboratory experiment was written by Fichter, Richard;Bonvicino, Guido E.. And the article was included in Journal of Chemical Education in 1985.Quality Control of 2-Aminopyrimidine-5-carbonitrile This article mentions the following:

An experiment for undergraduate organic chem. students is described in the preparation of 2-amino-5-bromopyridine by the bromination of 2-aminopyrimidine. The preparation of 2-amino-5-cyanopyrimidine from 2-amino-5-bromopyrimidine is also described. In the experiment, the researchers used many compounds, for example, 2-Aminopyrimidine-5-carbonitrile (cas: 1753-48-6Quality Control of 2-Aminopyrimidine-5-carbonitrile).

2-Aminopyrimidine-5-carbonitrile (cas: 1753-48-6) 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. 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.Quality Control of 2-Aminopyrimidine-5-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis of Silicon-Stereogenic Silanols Involving Iridium-Catalyzed Enantioselective C-H Silylation Leading to a New Ligand Scaffold was written by Zhang, Hongpeng;Zhao, Dongbing. And the article was included in ACS Catalysis in 2021.HPLC of Formula: 36057-44-0 This article mentions the following:

Despite a growing focus on the construction of highly enantioenriched silicon-stereogenic organosilicon compounds, the enantioselective synthesis of silicon-stereogenic silanols through asym. catalysis remains a considerable challenge. Herein, we realized enantioselective construction of silicon-stereogenic diarylsilanols via an Ir-catalyzed C-H silylation of diarylsilanols along with stereospecific substitution or Tamao-Fleming oxidation This strategy gives rise to a class of chiral diol catalyst cores (PSiOLs). Transformation of PSiOLs led to the ligand possessing both Si and P-stereocenters, which is capable of inducing excellent enantioselectivity in the rhodium(I)-catalyzed conjugate 1,4-addition of aryl boronic acids to cyclohexenone. In the experiment, the researchers used many compounds, for example, 4-methoxypicolinonitrile (cas: 36057-44-0HPLC of Formula: 36057-44-0).

4-methoxypicolinonitrile (cas: 36057-44-0) 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. 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.HPLC of Formula: 36057-44-0

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts