Category: nitriles-buliding-blocks

Synthesis and characterization of bis(2-cyanoethyl)aminoacetonitrile and tris(2-cyanoethyl)amine was written by Gao, Jian;Xu, Xing-you;Tang, Yan-ling;Zhang, Xing-yang. And the article was included in Huagong Kuangwu Yu Jiagong in 2003.Product Details of 7528-78-1 This article mentions the following:

Tile compounds were prepared from addition reaction of acrylonitrile with aminoacetonitrile and aqueous ammonia resp. It was characterized by IR spectra, ¹H-NMR, elemental anal., ES-MS and TG-DTA. The two compounds have similar thermal behaviors, and have high thermal stability under 300°C. In the experiment, the researchers used many compounds, for example, 3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1Product Details of 7528-78-1).

3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1) 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. 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.Product Details of 7528-78-1

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Development of Pd/C-Catalyzed Cyanation of Aryl Halides was written by Yu, Hannah;Richey, Rachel N.;Miller, William D.;Xu, Jiansheng;May, Scott A.. And the article was included in Journal of Organic Chemistry in 2011.Computed Properties of C6H5NS This article mentions the following:

A practical method for palladium-catalyzed cyanation of aryl halides using Pd/C is described. The new method can be applied to a variety of aryl bromide and active aryl chloride substrates to effect efficient conversions. The process features many advantages over existing cyanation conditions and the practical utility of the process has been demonstrated on scale. In the experiment, the researchers used many compounds, for example, 3-Methylthiophene-2-carbonitrile (cas: 55406-13-8Computed Properties of C6H5NS).

3-Methylthiophene-2-carbonitrile (cas: 55406-13-8) 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.Computed Properties of C6H5NS

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Nitrile – Wikipedia,
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Betti reaction enables efficient synthesis of 8-hydroxyquinoline inhibitors of 2-oxoglutarate oxygenases was written by Thinnes, C. C.;Tumber, A.;Yapp, C.;Scozzafava, G.;Yeh, T.;Chan, M. C.;Tran, T. A.;Hsu, K.;Tarhonskaya, H.;Walport, L. J.;Wilkins, S. E.;Martinez, E. D.;Muller, S.;Pugh, C. W.;Ratcliffe, P. J.;Brennan, P. E.;Kawamura, A.;Schofield, C. J.. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2015.Quality Control of 3-Methylthiophene-2-carbonitrile This article mentions the following:

There is interest in developing potent, selective, and cell-permeable inhibitors of human ferrous iron and 2-oxoglutarate (2OG) oxygenases for use in functional and target validation studies. The 3-component Betti reaction enables efficient one-step C-7 functionalization of modified 8-hydroxyquinolines (8HQs) to produce cell-active inhibitors of KDM4 histone demethylases and other 2OG oxygenases; the work exemplifies how a template-based metallo-enzyme inhibitor approach can be used to give biol. active compounds In the experiment, the researchers used many compounds, for example, 3-Methylthiophene-2-carbonitrile (cas: 55406-13-8Quality Control of 3-Methylthiophene-2-carbonitrile).

3-Methylthiophene-2-carbonitrile (cas: 55406-13-8) 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. 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 3-Methylthiophene-2-carbonitrile

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Nitrile – Wikipedia,
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A high-yielding preparation of β-keto nitriles was written by Ji, Yaohui;Trenkle, William C.;Vowles, James V.. And the article was included in Organic Letters in 2006.HPLC of Formula: 4435-14-7 This article mentions the following:

β-Keto nitriles are important precursors for a wide variety of biol. active heterocycles. A facile procedure for the high-yielding acylation of nitrile anions with unactivated esters to provide β-keto nitriles is reported. Thus, reaction of PhCH₂CH₂CN with PhCO₂Et in THF containing EtCMe₂OH K salt at room temperature for 10 min gave 95% PhCH₂CH(CN)COPh. The procedure is successful with enolizable and nonenolizable esters as well as hindered nitrile anions. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7HPLC of Formula: 4435-14-7).

2-Cyclohexylacetonitrile (cas: 4435-14-7) 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. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).HPLC of Formula: 4435-14-7

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Nitrile – Wikipedia,
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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

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Nitrile – Wikipedia,
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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,
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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,
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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,
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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,
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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