Category: nitriles-buliding-blocks

Conformational preferences of some substituted methyl groups in cyclohexanes as studies by carbon-13 nuclear magnetic resonance was written by Kitching, William;Olszowy, Henry;Adcock, William. And the article was included in Organic Magnetic Resonance in 1981.SDS of cas: 4435-14-7 This article mentions the following:

Low-temperature ¹³C NMR spectra of 80:20 mixtures of the cis and trans isomers of the disubstituted cyclohexanes I (R = Br, cyano, OH, OMe, SiMe₃, SnMe₃, PbMe₃, HgOAc) were recorded. After assignment of signals arising from the trans isomer, the conformational equilibrium of the cis components were determined by anal. of spectral intensities. From these the equilibrium A values of CH₂R (R as before) were calculated using the counter-poise approach. The values were similar to that of Me. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7SDS of cas: 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. 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.SDS of cas: 4435-14-7

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis of Fused Tetrazole Derivatives via a Tandem Cycloaddition and N-Allylation Reaction and Parallel Synthesis of Fused Tetrazole Amines was written by Ek, Fredrik;Manner, Sophie;Wistrand, Lars-Goeran;Frejd, Torbjoern. And the article was included in Journal of Organic Chemistry in 2004.Electric Literature of C8H5F3N2 This article mentions the following:

A method for the synthesis of novel fused tricyclic tetrazoles from allylic bromides generated by the recently discovered DiazAll reaction has been developed. This new tandem reaction comprises a cycloaddition between a nitrile and (TMS)N₃ followed by an intramol. N-allylation. The variation of functionalities in the benzene moiety was well-tolerated, and only a moderate difference in yield and degree of purity was noticed. An exo-methylene group in these new compounds permitted further derivatization. Structural resemblance with substances which possess important pharmacol. properties (e.g., losartan and flumazenil) motivated the synthesis of a series of ketones and a small library of amines. A comparison was made between the pharmacophore of (-)-epibatidine and a low energy conformation of N-methyl-5H-tetrazolo[5,1-a][2]benzazepin-6-amine. The reaction of 2-aminobenzonitrile derivatives with 3-bromo-2-(bromomethyl)-1-propene in the presence of tert-Bu nitrite gave 2-[2-(Bromomethyl)-2-propenyl]benzonitrile derivatives I (R = 5-Cl, 5-Br, 4-NO₂, 5-NO₂, 4-CF₃, 4-Cl-5-Br). Treatment of I with (azido)trimethylsilane in the presence of dibutyltin oxide and sequential ozonization gave 5H-tetrazolo[5,1-a][2]benzazepin-6-ones II (same R). Further reductive amination of II gave tetrazolo[5,1-a][2]benzazepin-6-amines III (same R, R¹ = H, PhCH₂; R¹R¹N = morpholino, etc.). In the experiment, the researchers used many compounds, for example, 2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1Electric Literature of C8H5F3N2).

2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1) 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).Electric Literature of C8H5F3N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Polymethylhydrosiloxane (PMHS)/trifluoroacetic acid (TFA): a novel system for reductive amination reactions was written by Patel, Jay P.;Li, An-Hu;Dong, Hanqing;Korlipara, Vijaya L.;Mulvihill, Mark J.. And the article was included in Tetrahedron Letters in 2009.Quality Control of 4-(Benzylamino)benzonitrile This article mentions the following:

Polymethylhydrosiloxane (PMHS)/trifluoroacetic acid (TFA) was discovered as a novel metal-free system for reductive amination reactions. A variety of (het)aryl amines as well as a representative carbamate and urea were successfully alkylated by benzaldehyde in the presence of PMHS and TFA in dichloromethane at room temperature in moderate to excellent yields (28-87%). Furthermore, this reaction protocol was successfully applied to the alkylation of p-nitroaniline with a wide range of aldehydes, ketones, and a representative acetal to obtain the alkylated products in yields ranging from 40% to 92%. The current work represents one of the very few examples of PMHS being activated by a Bronsted acid. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Quality Control of 4-(Benzylamino)benzonitrile).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) 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.Quality Control of 4-(Benzylamino)benzonitrile

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Nitrile – Wikipedia,
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Generation properties of 3-cyanocoumarins was written by Loboda, L. I.;Sokolova, I. V.;Degtyarenko, K. M.;Il’chenko, A. Ya.;Kropachev, A. V.. And the article was included in Izvestiya Vysshikh Uchebnykh Zavedenii, Fizika in 1988.Quality Control of 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile This article mentions the following:

The influence was investigated of 3-cyano substitution on the spectral-luminescent and generating properties of hydroxy- and diethylaminocoumarins. In both classes of coumarins, the CN-group decreases the region of rearrangement of the maximum of the generation wavelength: in the aminocoumarins, owing to a decrease in intermol. interactions with the solvents; and in the hydroxycoumarins, owing to a shift in the equilibrium of the protolytic reaction in the direction of the anionic form. As a result, the efficiency of the generation of the anionic form of the 3-CN-hydroxycoumarins increases. The generating capability of the aminocoumarins during a given substitution decreases, and the probability of forming nonplanar conformations of the mol. decreases. In the experiment, the researchers used many compounds, for example, 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6Quality Control of 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile).

7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6) 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.Quality Control of 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electrochemical Trifluoromethoxylation of (Hetero)aromatics with a Trifluoromethyl Source and Oxygen was written by Ouyang, Yao;Xu, Xiu-Hua;Qing, Feng-Ling. And the article was included in Angewandte Chemie, International Edition in 2022.COA of Formula: C8H4F3NO This article mentions the following:

A conceptually new and operationally simple protocol for the direct C-H trifluoromethoxylation of (hetero)aromatics by the combination of the readily available trifluoromethylating reagent and oxygen under electrochem. reaction conditions was discussed. This reaction proceeded through the initial generation of CF₃ radical followed by conversion to CF₃O radical, addition to (hetero)aromatics and rearomatization. The utility of this electrochem. trifluoromethoxylation was illustrated by the direct incorporation of CF₃O group into a variety of (hetero)aromatics as well as bio-relevant mols. In the experiment, the researchers used many compounds, for example, 2-(Trifluoromethoxy)benzonitrile (cas: 63968-85-4COA of Formula: C8H4F3NO).

2-(Trifluoromethoxy)benzonitrile (cas: 63968-85-4) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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.COA of Formula: C8H4F3NO

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

ZnO nanoparticle as catalyst for efficient green one-pot synthesis of coumarins through Knoevenagel condensation was written by Kumar, B. Vinay;Naik, Halehatty S.;Girija, D.;Kumar, B. Vijaya. And the article was included in Journal of Chemical Sciences (Bangalore, India) in 2011.Related Products of 51473-74-6 This article mentions the following:

Green chem. protocols with the reusability of the nano particle as catalyst in the synthesis of coumarins is described. The zinc oxide (ZnO) nanoparticles functions as highly effective catalyst for the reactions of various o-hydroxy benzaldehydes with 1,3-dicarbonyl compounds under microwave and thermal conditions to afford the corresponding coumarins in moderate to good yields. The catalyst is inexpensive, stable, can be easily recycled and reused for several cycles with consistent activity. In the experiment, the researchers used many compounds, for example, 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6Related Products of 51473-74-6).

7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. 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.Related Products of 51473-74-6

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Meisenheimer-type adducts from thiophene derivatives. Part 6. A kinetic and thermodynamic study of substituent effects on the formation of some non-gem adducts was written by Arnone, Caterina;Consiglio, Giovanni;Spinelli, Domenico;Dell’Erba, Carlo;Sancassan, Fernando;Terrier, Francois. And the article was included in Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999) in 1989.Application of 42137-24-6 This article mentions the following:

The rate and equilibrium constants for the formation of the Meisenheimer-type adducts I and II from 4-nitro-2-X- or 2-nitro-4-X-thiophenes and sodium methoxide have been measured at 25° in methanol or methanol-DMSO mixtures The observed stability and reactivity patterns have been interpreted in the light of the hyper-ortho relation in the thiophene ring and the special ability of the nitro group to stabilize effectively the adducts from a para-like position also. In the experiment, the researchers used many compounds, for example, 4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6Application of 42137-24-6).

4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. 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 42137-24-6

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Pyrrolo[1,2-a][1,4]benzodiazepine: A novel class of non-azole anti-dermatophyte anti-fungal agents was written by Meerpoel, Lieven;Van Gestel, Jef;Van Gerven, Frans;Woestenborghs, Filip;Marichal, Patrick;Sipido, Vic;Terence, Gilkerson;Nash, Roger;Corens, David;Richards, Ray D.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2005.HPLC of Formula: 53312-77-9 This article mentions the following:

Broad screening revealed compound I to be a novel anti-fungal agent with high specificity towards dermatophytes. The anti-fungal structure-activity relationship of this novel class of 5,6-dihydro-4H-pyrrolo[1,2-a][1,4]benzodiazepines is described together with its mode of action that appeared to be the inhibition of squalene epoxidase. Preliminary in vivo results of the most active compounds are also reported. In the experiment, the researchers used many compounds, for example, 2-Amino-3-chlorobenzonitrile (cas: 53312-77-9HPLC of Formula: 53312-77-9).

2-Amino-3-chlorobenzonitrile (cas: 53312-77-9) 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. 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: 53312-77-9

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A highly specific tetrazole-based chemosensor for fluoride ion: A new sensing functional group based on intramolecular proton transfer was written by Li, Ju-Ying;Zhou, Xin-Qi;Zhou, Yi;Fang, Yuan;Yao, Cheng. And the article was included in Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy in 2013.COA of Formula: C14H14N2O2 This article mentions the following:

A simple but highly selective colorimetric and fluorescent chemosensor for fluoride ion was prepared based on coumarin chromophore and 1H-tetrazole. Tetrazole functional group provided a novel sensing functional group containing the ESIPT structure for designing fluoride chemosensor. In the experiment, the researchers used many compounds, for example, 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6COA of Formula: C14H14N2O2).

7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6) 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.COA of Formula: C14H14N2O2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electrochemical reduction of pristinamycin I_A and related streptogramins in aqueous acidic medium was written by Largeron, M.;Vuilhorgne, M.;Le Potier, I.;Auziel, N.;Bacque, E.;Paris, J. M.;Fleury, M. B.. And the article was included in Tetrahedron in 1994.Recommanded Product: 10282-32-3 This article mentions the following:

The electrochem. reduction of the picolinoyl residue of pristinamycin I_A and related streptogramins was performed at a mercury cathode, in aqueous acidic medium. The presence of a peptidic lactone residue at the amide nitrogen atom markedly modified the expected cathodic behavior of pyridyl carboxamides: in particular, the pyridyl ring was reduced to tetrahydropyridine. Thanks to a series of model heterocyclic carboxamides, increasing steric hindrance at the amide nitrogen position was shown to lead to enhanced reduction of the heterocyclic ring. 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. 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.Recommanded Product: 10282-32-3

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts