Nitriles-buliding-blocks

Meisenheimer-type adducts from thiophene derivatives. Part 7. Interdependence of ¹³C NMR, thermodynamic and kinetic data was written by Dell’Erba, Carlo;Sancassan, Fernando;Novi, Marino;Spinelli, Domenico;Consiglio, Giovanni. And the article was included in Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999) in 1991.HPLC of Formula: 42137-24-6 This article mentions the following:

A ¹³C NMR study has been carried out in (CD₃)₂SO on the thiophene derivatives I (X = H, Ac, CN, etc.; R = H) and II (same X, R) and the related Meisenheimer adducts III and IV. The data obtained, and in particular the sums of the chem.-shift changes (∑ΔÎ? at C-3, C-4 and C-5, accompanying the formation of the adducts, are compared with the corresponding data previously obtained for analogous substrates I (same X, R = MeO) and II (same X, R = MeO) and adducts III and IV. The four series of ∑ΔÎ?values are then examined in the light of the already reported thermodn. (K_e) and kinetic (k₁) constants for the formation of the adducts. For a given X-substituent, log K_e values increase linearly as the corresponding absolute ∑ΔÎ?values decrease. On these grounds, the smaller π-electron-d. rearrangement accompanying the formation of gem-dimethoxy adducts emerges as an important factor, contributing to the larger observed K_e values. A further outcome is that, within a single series of adducts, a linear relationship of either log K_e or log₁ with ∑ΔÎ?holds only when excluding the terms with X = Ac or NO₂. Such findings are interpreted on the basis of the two-component nature of the substituent R effects: while for the nitro and the acetyl substituents the π-electron acceptor component is prevalent, the stabilizing effect of the other substituents is due mainly to a charge-dipole interaction. The anal. of some literature data for the benzene series fits the above conclusions. In the experiment, the researchers used many compounds, for example, 4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6HPLC of Formula: 42137-24-6).

4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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.HPLC of Formula: 42137-24-6

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Phototranspositions of cyanothiophenes: permutation pattern analysis and the chemical trapping of an intermediate 5-thiabicyclo[2.1.0]pent-2-ene was written by Barltrop, John A.;Day, A. Colin;Irving, Edward. And the article was included in Journal of the Chemical Society, Chemical Communications in 1979.SDS of cas: 55406-13-8 This article mentions the following:

Through their first excited singlet states, cyanothiophenes undergo phototranspositions for which permutation pattern anal. and the isolation of furan-thiabicyclopentene adducts (from irradiation in furan), suggest a mechanism involving 2,5-bonding followed by a ‘walk’ of the S atom. E.g., irradiation of 3-cyanothiophene in furan gave 71 and 7% resp., of the 1:1 adducts I and II. This result provides evidence for the intermediate III, for which I and II are the expected Diels-Alder adducts with furan; a similar result occurred with 2-cyanothiophene. In the experiment, the researchers used many compounds, for example, 3-Methylthiophene-2-carbonitrile (cas: 55406-13-8SDS of cas: 55406-13-8).

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. 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. SDS of cas: 55406-13-8

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Design and synthesis of novel tranilast analogs: Docking, antiproliferative evaluation and in-silico screening of TGFβR1 inhibitors was written by Ismail, Magda M. F.;El-Zahabi, Heba S. A.;Ibrahim, Rabab S.;Mehany, Ahmed B. M.. And the article was included in Bioorganic Chemistry in 2020.Recommanded Product: 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile This article mentions the following:

This work summarizes design, synthesis and biol. evaluation of sixteen novel tranilast analogs I [X = F, Cl, Br], II [X = F, O₂N], [X = H, Me; R¹ = OMe, Cl; R² = H, Cl], IV [Ar = 2-thiophenyl, 2,4-dimethylphenyl, 4-pyridinyl] and V [R = cyano, ethoxycarbonyl] on different tumors such as PC-3, HepG-2 and MCF-7 cell lines. The in-vitro cytotoxicity was evaluated using MTT assay showed that, twelve compounds out of sixteen showed higher cytotoxic activities (IC₅₀‘s 1.1-6.29μM), than that of the reference standard, 5-FU (IC₅₀ 7.53μM). The promising cytotoxic hits II [X = F], IV [Ar = 2-thiophenyl] and V [R = CN, X = 2,5-dimethoxy, n = 1; R = CN, X = OH, 2,5-dimethoxy, n = 0] proved to be selective to cancer cells when their cytotoxicity’s are examined on human normal cell line (WI-38). Then they were investigated for their possible mode of action as TGFβR1 inhibitors; remarkable inhibition of TGFβR1 by these hits was observed at the range of IC₅₀ 0.087-3.276μM. The cell cycle anal. of the most potent TGFβR1 inhibitor, II [X = O₂N] revealed cell cycle arrest at G2/M phase on prostate cancer cells. Addnl., it was clearly indicated apoptosis induction at Pre-G1 phase, this was substantiated by significant increase in the expression on the tumor suppressor gene, p53 and up regulation the level of apoptosis mediator, caspase-3. In addition, in-silico study was performed for validating the physicochem. and ADME properties which revealed that, all compounds were orally bioavailable with no side effects complying with Lipinski rule. The proposed mode of action was further explored on the light of mol. modeling simulation of the most potent compounds, II [X = O₂N] and V [n = 0, R = CN, X = 2,5-dimethoxy] which were docked into the active sites of TGFβR1 to predict their affinities toward the receptor. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Recommanded Product: 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile).

2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2) belongs to nitriles. Nitrile carbon shifts are in the range of 115�25 ppm whereas in isonitriles the shifts are around 155�65 ppm. 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.Recommanded Product: 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile

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Nitrile – Wikipedia,
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Rearrangement of the bromine atom in the demethylation of bromomethoxybenzoic acid. IV. 2-Bromoanisic acid and 3-bromoanisic acid was written by Tomita, Masao;Fujitani, Kazuyoshi. And the article was included in Yakugaku Zasshi in 1956.Related Products of 82380-17-4 This article mentions the following:

2,4-Br(MeO)C₆H₃CO₂H (XI), needles, m. 197-8°, was synthesized from 4-O₂NC₆H₄Me or p-cresol as a raw material. Nitration of 3-BrC₆H₄OH gave 3,4-Br(O₂N)C₆H₃OH, m. 125-31°, which was reduced to 3,4-Br(H₂N)C₆H₃OH, m. 151°; this was diazotized and treated with CuCN yielding 2,4-Br(HO)C₆H₃CN (XII), m. 151°. XI (0.5 g.), 15 ml. PhCl, and 2 g. AlCl₃ heated 1.5 hrs. on a water bath and the product poured on ice and extracted with Et₂O gave 0.3 g. 2,4-Br(HO)C₆H₃CO₂H (XIII), needles, m. 206-8° (from water); the m.p. of XIII given as 151° by Hodgson and Jenkinson (cf. C.A. 22,949) was confirmed to be the m.p. of XII. XI (1 g.) and 7 ml. HBr-AcOH in a sealed tube heated 5 hrs. at 130° and 2 hrs. at 150°, the product concentrated, neutralized with NaHCO₃ to remove the acidic substance, extracted with Et₂O, stirred with NaOH, and the NaOH layer acidified with HCl and extracted with Et₂O gave 3-BrC₆H₄OH (benzoate, m. 84-5°) and a small amount of XIII, m. 206-8°. XI (0.5 g.) and 6 ml. HCl-AcOH in a sealed tube heated 12 hrs. at 150° gave 0.45 g. XI. 2,4-Br(MeO)C₆H₃CO₂Me (XIV), plates, m. 29°, (1 g.) and 7 ml. HBr-AcOH in a sealed tube heated and the product treated as usual gave 3-BrC₆H₄OH. Similarly, 3,4-Br(MeO)C₆H₃CO₂H gave 3,4-Br(HO)C₆H₃CO₂H, m. 106-7°. 3,4-Br(MeO)C₆H₃CO₂Me (0.5 g.) gave 0.3 g. 3,5,4-Br₂(HO)C₆H₂CO₂H, m. 253-7° (decomposition), and 0.1 g. 3,4-Br(HO)C₆H₃CO₂H, m. 175-7° (Me ester, m. 107°). In the experiment, the researchers used many compounds, for example, 2-Bromo-4-hydroxybenzonitrile (cas: 82380-17-4Related Products of 82380-17-4).

2-Bromo-4-hydroxybenzonitrile (cas: 82380-17-4) 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.Related Products of 82380-17-4

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A cost-effective and green aqueous synthesis of 3-substituted coumarins catalyzed by potassium phthalimide was written by Kiyani, Hamzeh;Daroonkala, Masoumeh Darzi. And the article was included in Bulletin of the Chemical Society of Ethiopia in 2015.Related Products of 51473-74-6 This article mentions the following:

An efficient procedure for the synthesis of various 3-substituted coumarins I [R = H, 6-Br, 7-NEt₂, 8-OMe; R¹ = CN, COOH; X = O] as well as 2-imino-2H-chromenes I [R¹ = CN; X = NH] was developed via potassium phthalimide-catalyzed Knoevenagel condensation reaction of salicylaldehydes with active methylene compounds under aqueous conditions at room temperature This approach provided many merits such as high yields of products, simple work-up procedure, waste free and mild reaction conditions, com. available organocatalyst and the use of water as environmentally benign solvent. 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. 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. 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.Related Products of 51473-74-6

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

N-Demethylation of N,N-Dimethylanilines by the Benzotriazole N-Oxyl Radical: Evidence for a Two-Step Electron Transfer-Proton Transfer Mechanism was written by Baciocchi, Enrico;Bietti, Massimo;Lanzalunga, Osvaldo;Lapi, Andrea;Raponi, Daniele. And the article was included in Journal of Organic Chemistry in 2010.COA of Formula: C9H10N2 This article mentions the following:

The reaction of the benzotriazole N-oxyl radical (BTNO) with a series of 4-X-N,N-dimethylanilines (X = CN, CF₃, CO₂CH₂CH₃, CH₃, OC₆H₅, OCH₃) has been investigated in CH₃CN. Product anal. shows that the radical, 4-X-C₆H₄N(CH₃)CH₂^·, is first formed, which can lead to the N-demethylated product or the product of coupling with BTNO. Reaction rates were found to increase significantly by increasing the electron-donating power of the aryl substituents (ρ⁺ = -3.8). With electron-donating substituents (X = CH₃, OC₆H₅, OCH₃), no intermol. deuterium kinetic isotope effect (DKIE) and a substantial intramol. DKIE are observed With electron-withdrawing substituents (X = CN, CF₃, CO₂CH₂CH₃), substantial values of both intermol. and intramol. DKIEs are observed These results can be interpreted on the basis of an electron-transfer mechanism from the N,N-dimethylanilines to the BTNO radical followed by deprotonation of the anilinium radical cation (ET-PT mechanism). By applying the Marcus equation to the kinetic data for X = CH₃, OC₆H₅, OCH₃ (rate-determining ET), a reorganization energy for the ET reaction was determined (λ_BTNO/DMA = 32.1 kcal mol^-1). From the self-exchange reorganization energy for the BTNO/BTNO^– couple, a self-exchange reorganization energy value of 31.9 kcal mol^-1 was calculated for the DMA^·1/DMA couple. In the experiment, the researchers used many compounds, for example, 4-(Ethylamino)benzonitrile (cas: 4714-63-0COA of Formula: C9H10N2).

4-(Ethylamino)benzonitrile (cas: 4714-63-0) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. 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. COA of Formula: C9H10N2

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Nitrile – Wikipedia,
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General Reductive Amination of Aldehydes and Ketones with Amines and Nitroaromatics under H₂ by Recyclable Iridium Catalysts was written by Sui, Dejun;Mao, Fei;Fan, Haipeng;Qi, Zhengliang;Huang, Jun. And the article was included in Chinese Journal of Chemistry in 2017.Computed Properties of C14H12N2 This article mentions the following:

Heterogeneous iridium catalysts were prepared and applied for the reductive amination of aldehydes and ketones with nitroaroms. and amines using H₂. The iridium catalysts were prepared by pyrolysis of ionic liquid 1-methyl-3-cyanomethylimidazoulium chloride ([MCNI]Cl) with iridium chloride (IrCl₃) in activated carbons. Iridium particles were well dispersed and stable in the N-doped carbon materials from [MCNI]Cl with activated carbon. The Ir@NC(600-2h) catalyst was found to be highly active and selective for the reductive amination of aldehydes and ketones using H₂ and a variety of nitrobenzenes and amines were selectively converted into the corresponding secondary and tertiary amines. The Ir@NC(600-2h) catalyst was reusable several times without evident deactivation. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Computed Properties 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.Computed Properties of C14H12N2

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Simple, efficient catalyst system for the palladium-catalyzed amination of aryl chlorides, bromides, and triflates was written by Wolfe, John P.;Tomori, Hiroshi;Sadighi, Joseph P.;Yin, Jingjun;Buchwald, Stephen L.. And the article was included in Journal of Organic Chemistry in 2000.Electric Literature of C14H12N2 This article mentions the following:

Palladium complexes supported by (2-PhC₆H₄)P(CMe₃)₂ (I) or (2-PhC₆H₄)PCy₂ (II; Cy = cyclohexyl) are efficient catalysts for the catalytic amination of a wide variety of aryl halides and triflates. Use of ligand I allows for the room-temperature catalytic amination of many aryl chloride, bromide, and triflate substrates, while ligand II is effective for the amination of functionalized substrates or reactions of acyclic secondary amines. The catalysts perform well for a large number of different substrate combinations at 80-110°, including chloropyridines and functionalized aryl halides and triflates using 0.5-1.0 mol% Pd; some reactions proceed efficiently at low catalyst levels (0.05 mol% Pd). These ligands are effective for almost all substrate combinations that have been previously reported with various other ligands, and they represent the most generally effective catalyst system reported to date. I and II are air-stable, crystalline solids that are com. available. Their effectiveness is due to a combination of steric and electronic properties that promote oxidative addition, Pd-N bond formation, and reductive elimination. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Electric Literature of C14H12N2).

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. 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.Electric Literature of C14H12N2

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Base-promoted N-alkylation using formamides as the N-sources in neat water was written by Chen, Wen-Xin;Zhang, Cai-Yun;Shao, Li-Xiong. And the article was included in Tetrahedron in 2014.Related Products of 37812-51-4 This article mentions the following:

An efficient catalyst-free, alternative method for the C-N bond formation reaction of alkyl electrophiles using formamides as the N-sources was achieved under mild conditions. The reaction possesses the advantages of a broad range of substrates scope and wide functional group tolerance. It should also be noted that this process was performed using the environmentally benign water as the sole solvent, and high yield can also be achieved in ten-gram scale. In the experiment, the researchers used many compounds, for example, 4-(Morpholinomethyl)benzonitrile (cas: 37812-51-4Related Products of 37812-51-4).

4-(Morpholinomethyl)benzonitrile (cas: 37812-51-4) 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. 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.Related Products of 37812-51-4

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ZrCl₄/[bmim]BF₄-Catalyzed condensation of salicylaldehydes and malononitrile: Single-step synthesis of 3-cyanocoumarin derivatives was written by Valizadeh, Hassan;Mahmoodian, Manzar;Gholipour, Hamid. And the article was included in Journal of Heterocyclic Chemistry in 2011.Computed Properties of C14H14N2O2 This article mentions the following:

A versatile and efficient single-step route to 3-cyanocoumarins via Knoevenagel condensation of salicylaldehydes and malononitrile using ZrCl₄ as the catalyst (15 mol %) in ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate as reaction medium and catalyst is described. The novel procedure features single step, short reaction time, good yields, and simple workup. J. Heterocyclic Chem., (2011). In the experiment, the researchers used many compounds, for example, 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6Computed Properties of C14H14N2O2).

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts