Nitriles-buliding-blocks

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

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Nitrile – Wikipedia,
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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

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Nitrile – Wikipedia,
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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

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Nitrile – Wikipedia,
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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

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Nitrile – Wikipedia,
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Tellurium tetrachloride-olefin addition compounds was written by Arpe, Hans J.;Kuckertz, Herbert. And the article was included in Angewandte Chemie, International Edition in English in 1971.Formula: C8H13N This article mentions the following:

Propylene and butadiene react with TeCl4 to give Cl2Te(C3H6Cl)2 and Cl2Te(CH2CH:CHCH2Cl)2. The reaction of TeCl4 with ethylene is slower, the (2-chloroethyl)tellurium chlorides, Cl2Te(CH2CH2Cl)2 and Cl3TeCH2CH2Cl, are obtained. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Formula: C8H13N).

2-Cyclohexylacetonitrile (cas: 4435-14-7) 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. 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: C8H13N

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Palladium-catalyzed silane/siloxane reductions in the one-pot conversion of nitro compounds into their amines, hydroxylamines, amides, sulfonamides, and carbamates was written by Rahaim, Ronald J. Jr.;Maleczka, Robert E. Jr.. And the article was included in Synthesis in 2006.HPLC of Formula: 1483-54-1 This article mentions the following:

A combination of palladium(II) acetate, aqueous potassium fluoride, and polymethylhydrosiloxane (PMHS) facilitates the room-temperature reduction of aromatic nitro compounds to anilines. These reactions tend to be quick (30 min), high-yielding, and tolerate a range of other functional groups. Replacement of PMHS/KF with triethylsilane allows for the reduction of aliphatic nitro compounds to their corresponding hydroxylamines. Depending on the substrate, both conditions can allow for the in situ conversion of the product amines into amides, sulfonamides, and carbamates. In the experiment, the researchers used many compounds, for example, 2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1HPLC of Formula: 1483-54-1).

2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1) 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. 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: 1483-54-1

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

1,2,4-Triazolo-[1,5-a]pyridine HIF Prolylhydroxylase Domain-1 (PHD-1) Inhibitors With a Novel Monodentate Binding Interaction was written by Ahmed, Saleh;Ayscough, Andrew;Barker, Greg R.;Canning, Hannah E.;Davenport, Richard;Downham, Robert;Harrison, David;Jenkins, Kerry;Kinsella, Natasha;Livermore, David G.;Wright, Susanne;Ivetac, Anthony D.;Skene, Robert;Wilkens, Steven J.;Webster, Natalie A.;Hendrick, Alan G.. And the article was included in Journal of Medicinal Chemistry in 2017.SDS of cas: 1114546-30-3 This article mentions the following:

Herein the authors describe the identification of 4-{[1,2,4]triazolo[1,5-a]pyridin-5-yl}benzonitrile-based inhibitors of the hypoxia-inducible factor prolylhydroxylase domain-1 (PHD-1) enzyme. These inhibitors were shown to possess a novel binding mode by x-ray crystallog., in which the triazolo N1 atom coordinates in a hitherto unreported monodentate interaction with the active site Fe²⁺ ion, while the benzonitrile group accepts a hydrogen-bonding interaction from the side chain residue of Asn 315. Further optimization led to potent PHD-1 inhibitors with good physicochem. and pharmacokinetic properties. In the experiment, the researchers used many compounds, for example, 4-Bromo-2-fluoro-3-methylbenzonitrile (cas: 1114546-30-3SDS of cas: 1114546-30-3).

4-Bromo-2-fluoro-3-methylbenzonitrile (cas: 1114546-30-3) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).SDS of cas: 1114546-30-3

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reactions of acetonitrile in a radiofrequency discharge was written by So, Ying Hung;Bezuk, Steve J.;Miller, Larry L.. And the article was included in Journal of Organic Chemistry in 1982.Synthetic Route of C8H13N This article mentions the following:

MeCN passed through an inductively coupled rf discharge under various conditions of power and flow rate gave, as the principal products EtCN, ethane and HCN. Reaction of mixtures of MeCN and cyclohexane gave the same 3 products and cyanocyclohexylmethane, methylcyclohexane, and cyclohexene. All 6 products can be rationalized by neutral radical reactions. Emission spectroscopy of MeCN plasmas showed the expected CN bands from the excited A²π and B²Σ⁺ states. Anal. of the peak intensities gave a vibrational temperature of ∼5900 °K and rotational temperature of ∼735 °K for the B²Σ⁺ state. Lower power, higher pressure, or added ethane diminished the emission intensity but did not change these temperatures Added Ar had no effect up to a mol fraction of Ar of 0.8. The absence of cyanoalkanes from plasmas containing CN and alkyl radicals was observed In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Synthetic Route of C8H13N).

2-Cyclohexylacetonitrile (cas: 4435-14-7) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. 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.Synthetic Route of C8H13N

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis of Secondary Amines from One-Pot Reductive Amination with Formic Acid as the Hydrogen Donor over an Acid-Resistant Cobalt Catalyst was written by Jiang, Liang;Zhou, Peng;Zhang, Zehui;Jin, Shiwei;Chi, Quan. And the article was included in Industrial & Engineering Chemistry Research in 2017.Synthetic Route of C14H12N2 This article mentions the following:

Developing new heterogeneous non-noble metal catalysts to replace noble-metal catalysts in organic transformations is of high importance in modern synthetic chem. Herein, nitrogen-doped carbon embedded Co catalysts (abbreviated as Co@CN-T-AT, in which T represents the pyrolysis temperature, AT represents the acid-leaching process) were prepared through the simple pyrolysis of graphene oxide-supported cobalt-based zeolitic imidazolate-frameworks, followed by the acid-leaching process. The Co@CN-600-AT catalyst demonstrated the highest catalytic activity among the synthesized Co catalyst toward the reductive amination of carbonyl compounds with nitro compounds by transfer hydrogenation with formic acid as the hydrogen donor, which integrated three consecutive steps into a one-pot reaction. By applying this catalyst, structurally diverse secondary amines were produced in good to excellent yields without the reduction of other functional groups. The transfer hydrogenation of the imines (C=N bonds) was the rate-determining step. Furthermore, the catalyst was highly stable and could be reused without decrease of the catalytic activity. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Synthetic Route of C14H12N2).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) 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 C14H12N2

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Liquid-crystalline compounds. X. trans-4-Cyanocyclohexanol derivatives with liquid-crystalline properties was written by Praefcke, Klaus;Schmidt, Dietmar. And the article was included in Chemiker-Zeitung in 1981.HPLC of Formula: 24056-34-6 This article mentions the following:

Nine trans-4-cyanocyclohexyl esters (I and II, R¹ = C₅H₁₁, C₇H₁₅, C₉H₁₉; and III, R² = Pr, C₅H₁₁, C₇H₁₅) were prepared by converting the appropriate carboxylic acids into their acid chlorides and esterifying them with trans-4-cyanocyclohexanol; the esters exhibited both nematic and isotropic liquid crystal phases. cis-4-Cyanocyclohexyl trans–p-(4-propylcyclohexyl)benzoate, which showed a nematic phase, was prepared similarly. In the experiment, the researchers used many compounds, for example, 4-Hydroxycyclohexanecarbonitrile (cas: 24056-34-6HPLC of Formula: 24056-34-6).

4-Hydroxycyclohexanecarbonitrile (cas: 24056-34-6) 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 addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).HPLC of Formula: 24056-34-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts