Category: nitriles-buliding-blocks

A convenient method for the α-carbethoxylation of alkylnitriles was written by Albarella, James Paul. And the article was included in Journal of Organic Chemistry in 1977.Name: 2-Cyclohexylacetonitrile This article mentions the following:

Treatment of RCH2CN (R = C3-16 alkyl) in THF at -78° with 2.3 molar equiv LiN(CHMe2)2 followed by 1.02-1.05 molar equiv (EtO)2CO or ClCO2Et gave excellent yields of the resp. RCH(CN)CO2Et. Similarly prepared were Et 2-cyano-2-cyclopentylacetate and the cyclohexyl analog. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Name: 2-Cyclohexylacetonitrile).

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

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis of Tertiary Benzylic Nitriles via Nickel-Catalyzed Markovnikov Hydrocyanation of α-Substituted Styrenes was written by Xing, Yidan;Yu, Rongrong;Fang, Xianjie. And the article was included in Organic Letters in 2020.Recommanded Product: 5351-07-5 This article mentions the following:

The Markovnikov hydrocyanation of α-substituted styrenes enables the synthesis of tertiary benzylic nitriles under nickel catalysis. The Lewis-acid-free transformation features an unprecedented functional groups tolerance, including the -OH and -NH₂ groups. A broad range of tertiary benzylic nitriles were obtained in good to excellent yields. In addition, an asym. version of this reaction was preliminarily investigated. In the experiment, the researchers used many compounds, for example, 2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5Recommanded Product: 5351-07-5).

2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5) 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.Recommanded Product: 5351-07-5

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Nitrile – Wikipedia,
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Non-covalent thrombin inhibitors featuring P₃-heterocycles with P₁-monocyclic arginine surrogates was written by Reiner, John E.;Siev, Daniel V.;Araldi, Gian-Luca;Cui, Jingrong Jean;Ho, Jonathan Z.;Reddy, Komandla Malla;Mamedova, Lala;Vu, Phong H.;Lee, Kuen-Shan S.;Minami, Nathaniel K.;Gibson, Tony S.;Anderson, Susanne M.;Bradbury, Annette E.;Nolan, Thomas G.;Semple, J. Edward. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2002.Safety of 3-Amino-4-methylbenzonitrile This article mentions the following:

Investigations on P₂-P₃-heterocyclic dipeptide surrogates directed towards identification of an orally bioavailable thrombin inhibitor led us to pursue novel classes of achiral, non-covalent P₁-arginine derivatives The design, synthesis, and biol. activity of inhibitors NC1-NC30 that feature three classes of monocyclic P₁-arginine surrogates will be disclosed: (1) (hetero)aromatic amidines, amines and hydroxyamidines, (2) 2-aminopyrazines, and (3) 2-aminopyrimidines and 2-aminotetrahydropyrimidines. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methylbenzonitrile (cas: 60710-80-7Safety of 3-Amino-4-methylbenzonitrile).

3-Amino-4-methylbenzonitrile (cas: 60710-80-7) 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.Safety of 3-Amino-4-methylbenzonitrile

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Nitrile – Wikipedia,
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Synthesis and application of 4-(coumarin-3-yl)thiophenes was written by Sabnis, Ram W.;Rangnekar, Dinesh W.. And the article was included in Sulfur Letters in 1993.Computed Properties of C12H14N2O4S This article mentions the following:

A facile synthesis of (4-coumarin-3-yl)thiophenes I (R¹ = H, OMe, R² = H, OH, OMe, NEt₂, R³ = H, OH, OMe, Cl, NO₂, R⁴ = H, OMe) was achieved by the condensation of 2-acetamido-3-cyano-4-carbethoxymethylene-5-carbethoxythiophene II with selected o-hydroxy aldehydes III in the presence of piperidine. The key intermediate II was synthesized by cyclocondensation of EtO₂CCH₂COCH₂CO₂Et, sulfur, and malononitrile by a Gewald synthesis followed by acetylation. I were applied on polyester fibers as fluorescent disperse dyes and their fluorescence and dyeing properties were studied. In the experiment, the researchers used many compounds, for example, Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate (cas: 58168-20-0Computed Properties of C12H14N2O4S).

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. 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. Computed Properties of C12H14N2O4S

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Water-Soluble Iridium N-Heterocyclic Carbene Complexes for the Alkylation of Amines with Alcohols was written by Fernandes, Ana;Royo, Beatriz. And the article was included in ChemCatChem in 2017.Synthetic Route of C14H12N2 This article mentions the following:

A new series of water-soluble Ir complexes with N-heterocyclic carbene ligands that bearing ester and amide groups were obtained and fully characterized. The new complexes were highly reactive and selective for the alkylation of amines with alcs. with a 1:1 ratio of reactants in water and in the absence of base or other additives. The catalytic system had a broad substrate scope, which allowed the synthesis of a variety of primary and secondary amines in excellent yields. A tolerance to a large range of functional groups was obtained. 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. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Synthetic Route of C14H12N2

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Nitrile – Wikipedia,
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Synthesis and pharmacological study of 5,6,8,9-tetrahydro-4H,7H-pyrrolo[1,2-a]cyclopenta[b]thieno[3,2-f][1,4]diazepines was written by Vega, S.;Gil, M. Soledad;Darias, V.;Sanchez Mateo, Candelaria C.;Exposito, Maria A.. And the article was included in Pharmazie in 1995.SDS of cas: 70291-62-2 This article mentions the following:

The paper reports the synthesis of a series of 5,6,8,9-tetrahydro-4H,7H-pyrrolo[1,2-a]cyclopenta[b]thieno[3,2-f][1,4]diazepines and the results of the study on their CNS activity in mice. The pharmacol. properties of a previously prepared series of 5,6,7,8,9,10-hexahydrobenzo analogs is also described. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2SDS of cas: 70291-62-2).

2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2) 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.SDS of cas: 70291-62-2

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Nitrile – Wikipedia,
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Ir(III)-Catalysed electrooxidative intramolecular dehydrogenative C-H/N-H coupling for the synthesis of N-H indoles was written by Kim, Youyoung;Kim, Dongwook;Chang, Sukbok. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2021.Safety of 2-Amino-4-(trifluoromethyl)benzonitrile This article mentions the following:

An iridium(III)-catalyzed electrooxidative intramol. dehydrogenative C-H/N-H coupling of unprotected 2-alkenyl anilines was described. The developed method allowed the synthesis of a variety of 3-substituted N-H indole scaffolds under undivided electrolytic conditions. Mechanistic studies suggested that the reaction proceeds through the electro-oxidation induced reductive elimination pathway. In the experiment, the researchers used many compounds, for example, 2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1Safety of 2-Amino-4-(trifluoromethyl)benzonitrile).

2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1) 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. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Safety of 2-Amino-4-(trifluoromethyl)benzonitrile

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Nitrile – Wikipedia,
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A Metalloligand Appended with Thiazole Rings: Heterometallic {Co³⁺-Zn²⁺} and {Co³⁺-Cd²⁺} Complexes and Their Heterogeneous Catalytic Applications was written by Bansal, Deepak;Hundal, Geeta;Gupta, Rajeev. And the article was included in European Journal of Inorganic Chemistry in 2015.Computed Properties of C18H10N2 This article mentions the following:

This work describes a Co³⁺-based metalloligand containing appended thiazole rings and its reactions with secondary metal ions to produce heterometallic {Co³⁺-Zn²⁺} and {Co³⁺-Cd²⁺} complexes. Structural studies show that some of the appended thiazole rings from the metalloligand coordinate to secondary metal ions, whereas the remaining ones act as hydrogen-bond acceptors to metal-bound CH₃OH or H₂O mols. These heterometallic complexes function as reusable heterogeneous catalysts for the ring-opening reactions of epoxides as well as cyanation and Knoevenagel condensation reactions of aldehydes. The catalytic results illustrate that the microenvironment remains intact during the catalysis and potentially enhances the substrate interaction with the Lewis acidic secondary metal ions. 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. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Computed Properties of C18H10N2

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

BF₃·Et₂O as a metal-free catalyst for direct reductive amination of aldehydes with amines using formic acid as a reductant was written by Luo, Zhenli;Pan, Yixiao;Yao, Zhen;Yang, Ji;Zhang, Xin;Liu, Xintong;Xu, Lijin;Fan, Qing-Hua. And the article was included in Green Chemistry in 2021.Application of 10282-32-3 This article mentions the following:

A versatile metal- and base-free direct reductive amination of aldehydes with amines using formic acid as a reductant under the catalysis of inexpensive BF₃·Et₂O has been developed. A wide range of primary and secondary amines and diversely substituted aldehydes are compatible with this transformation, allowing facile access to various secondary and tertiary amines in high yields with wide functional group tolerance. Moreover, the method is convenient for the late-stage functionalization of bioactive compounds and preparation of commercialized drug mols. and biol. relevant N-heterocycles. The procedure has the advantages of simple operation and workup and easy scale-up, and does not require dry conditions, an inert atm. or a water scavenger. Mechanistic studies reveal the involvement of imine activation by BF₃ and hydride transfer from formic acid. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Application of 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. 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.Application of 10282-32-3

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Palladium(II)-Catalyzed Three-Component Tandem Cyclization Reaction for the One-Pot Assembly of 4-Arylquinazolines was written by Wang, Zijuan;Chen, Wenteng;He, Chang;Zhang, Guolin;Yu, Yongping. And the article was included in Synthesis in 2021.Synthetic Route of C7H5ClN2 This article mentions the following:

A one-pot method for joining three sep. components leading to an assortment of 4-arylquinazolines I (R¹ = H, 6-Cl, 7-Cl, 8-Cl, 6-Me, 6-Br; R² = H, Me, Ph; R³ = C₆H₅, 4-ClC₆H₄, 4-CH₃C₆H₄, etc.) in good to excellent yields is described. The method consists of a palladium(II)-catalyzed cascade reaction involving C(sp)-C(sp²) coupling followed by intramol. C-N bond formation. The reaction was readily scaled up to gram quantity and successfully applied to the synthesis of a translocator protein (TSPO) ligand II. In the experiment, the researchers used many compounds, for example, 2-Amino-3-chlorobenzonitrile (cas: 53312-77-9Synthetic Route of C7H5ClN2).

2-Amino-3-chlorobenzonitrile (cas: 53312-77-9) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. 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.Synthetic Route of C7H5ClN2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts