Author: Jessica.F

Ligand-Promoted Non-Directed C-H Cyanation of Arenes was written by Liu, Luo-Yan;Yeung, Kap-Sun;Yu, Jin-Quan. And the article was included in Chemistry – A European Journal in 2019.Quality Control of 3-(tert-Butyl)benzonitrile This article mentions the following:

The first example of a 2-pyridone accelerated non-directed C-H cyanation with an arene as the limiting reagent was reported. This protocol was compatible with a broad scope of arenes, including advanced intermediates, drug mols. and natural products. A kinetic isotope experiment (k_H/k_D=4.40) indicated that the C-H bond cleavage is the rate-limiting step. Also, the reaction is readily scalable, further showcasing the synthetic utility of this method. In the experiment, the researchers used many compounds, for example, 3-(tert-Butyl)benzonitrile (cas: 154532-34-0Quality Control of 3-(tert-Butyl)benzonitrile).

3-(tert-Butyl)benzonitrile (cas: 154532-34-0) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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.Quality Control of 3-(tert-Butyl)benzonitrile

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Mild and General Methods for the Palladium-Catalyzed Cyanation of Aryl and Heteroaryl Chlorides was written by Littke, Adam;Soumeillant, Maxime;Kaltenbach, Robert F. III;Cherney, Robert J.;Tarby, Christine M.;Kiau, Susanne. And the article was included in Organic Letters in 2007.Safety of 3-Methylthiophene-2-carbonitrile This article mentions the following:

New methods for the palladium-catalyzed cyanation of aryl and heteroaryl chlorides have been developed, featuring sterically demanding, electron-rich phosphines. E.g., Pd(TFA)₂/(binaphthyl)P(t-Bu)₂/Zn catalyzed the cyanation of 4-ClC₆H₄NH₂ by Zn(CN)₂ to give 93% 4-NCC₆H₄NH₂. Highly challenging electron-rich aryl chlorides, in addition to electron-neutral and electron-deficient substrates, as well as nitrogen- and sulfur-containing heteroaryl chlorides can all undergo efficient cyanation under relatively mild conditions using readily available materials. In terms of substrate scope and temperature, these methods compare very favorably with the state-of-the-art cyanations of aryl chlorides. In the experiment, the researchers used many compounds, for example, 3-Methylthiophene-2-carbonitrile (cas: 55406-13-8Safety of 3-Methylthiophene-2-carbonitrile).

3-Methylthiophene-2-carbonitrile (cas: 55406-13-8) belongs to nitriles. Nitrile carbon shifts are in the range of 115�25 ppm whereas in isonitriles the shifts are around 155�65 ppm. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Safety of 3-Methylthiophene-2-carbonitrile

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Nitrile – Wikipedia,
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Dehydrogenation and α-functionalization of secondary amines by visible-light-mediated catalysis was written by Stanek, Filip;Pawlowski, Robert;Morawska, Paulina;Bujok, Robert;Stodulski, Maciej. And the article was included in Organic & Biomolecular Chemistry in 2020.Related Products of 10282-32-3 This article mentions the following:

A visible-light-mediated process for dehydrogenation of amines was described for the synthesis of imines. The given protocol showed a broad substrate scope, mild reaction conditions and excellent results without the requirement of tedious purification This process could be applied in one-pot functionalization of secondary amines with various nucleophiles through the cooperation of visible-light and Lewis acid catalysis, leading to the structurally varied essential components of biol. active mols. In addition, Stern-Volmer studies and quenching experiments revealed the role of a catalyst and led to the proposed mechanism of this transformation. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Related Products of 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. 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.Related Products of 10282-32-3

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Nitrile – Wikipedia,
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Fungal hydroxylation of ethyl benzene and derivatives was written by Holland, Herbert L.;Carter, Ian M.;Chenchaiah, P. Chinna;Khan, Shaheer H.;Munoz, Benito;Ninniss, Ronald W.;Richards, Denise. And the article was included in Tetrahedron Letters in 1985.Formula: C9H9NO This article mentions the following:

The fungus Mortierella isabellina converted Et benzene and a number of para-substituted derivatives to the corresponding optically active 1-phenylethanols with enantiomeric excesses of 5-40%. H removal from the substrate precedes product formation and is stereochem. independent of it. In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6Formula: C9H9NO).

(R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6) 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. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Formula: C9H9NO

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Highly potent macrocyclic BACE-1 inhibitors incorporating a hydroxyethylamine core: Design, synthesis and X-ray crystal structures of enzyme inhibitor complexes was written by Sandgren, Veronica;Agback, Tatiana;Johansson, Per-Ola;Lindberg, Jimmy;Kvarnstroem, Ingemar;Samuelsson, Bertil;Belda, Oscar;Dahlgren, Anders. And the article was included in Bioorganic & Medicinal Chemistry in 2012.COA of Formula: C11H13N This article mentions the following:

A series of P1-P3 linked macrocyclic BACE-1 inhibitors containing a hydroxyethylamine (HEA) isostere scaffold has been synthesized. All inhibitors comprise a toluene or N-phenylmethanesulfonamide P2 moiety. Excellent BACE-1 potencies, both in enzymic and cell-based assays, were observed in this series of target compounds, with the best candidates displaying cell-based IC₅₀ values in the low nanomolar range. As an attempt to improve potency, a Ph substituent aiming at the S3 subpocket was introduced in the macrocyclic ring. X-ray analyzes were performed on selected compounds, and enzyme-inhibitor interactions are discussed. In the experiment, the researchers used many compounds, for example, 3-(tert-Butyl)benzonitrile (cas: 154532-34-0COA of Formula: C11H13N).

3-(tert-Butyl)benzonitrile (cas: 154532-34-0) 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 addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).COA of Formula: C11H13N

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Nitrile – Wikipedia,
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A carbon-13 NMR study of 5-cyano-, 5-methoxycarbonyl-, 5-carbamoyl-, and 5-acetyl-3-nitro-2-X-thiophenes: substituent effects and their relation to the charge distribution in corresponding 2,2-dimethoxy Meisenheimer adducts was written by Dell’Erba, Carlo;Sancassan, Fernando;Novi, Marino;Spinelli, Domenico;Consiglio, Giovanni;Arnone, Caterina;Ferroni, Fiammetta. And the article was included in Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999) in 1989.Synthetic Route of C5H2N2O2S This article mentions the following:

A ¹³C NMR study in (CD₃)₂SO has been carried out on 5-cyano- (I), 5-methoxycarbonyl- (II), 5-carbamoyl- (III), and 5-acetyl-3-nitro-2-X-thiophenes (IV) in order to investigate the 2-X-substituent effect on the C(α) chem. shifts of the different 5-probes. The results obtained show that, unlike the case of the acetyl group, the α-carbon chem. shifts of the cyano, methoxycarbonyl, and carbamoyl groups are not appreciably affected by through-conjugation with the 2-X-substituents, π-polarization being the more important outcome of the substituent effect on the probe group. The anal. of both the C(5) and C(α) chem.-shift variations in I–IV by a gradual modification of the electron-releasing power of the substituents reveals a trend which has been interpreted as a useful indicator of the electronic effects in play on the distribution of the π-electron densities in the corresponding Meisenheimer adducts V (R = CN, CO₂Me, CONH, Ac). In the experiment, the researchers used many compounds, for example, 4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6Synthetic Route of C5H2N2O2S).

4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6) 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.Synthetic Route of C5H2N2O2S

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Amino-functionalized Zr(IV) metal-organic framework as bifunctional acid-base catalyst for Knoevenagel condensation was written by Yang, Yang;Yao, Hong-Fei;Xi, Fu-Gui;Gao, En-Qing. And the article was included in Journal of Molecular Catalysis A: Chemical in 2014.SDS of cas: 55490-87-4 This article mentions the following:

The amino-functionalized metal-organic framework of Zr(IV) with 2-aminoterephthalate, UiO-66-NH₂, was studied as a solid catalyst for Knoevenagel condensation. The material can efficiently catalyze the condensation reaction of benzaldehyde with Et cyanoacetate or malononitrile in highly polar solvents such as DMF, DMSO and ethanol. The catalytic system has also been tested for various aromatic aldehydes, the conversion easily reaching more than 90% under mild conditions. It was demonstrated that the catalytic process is heterogeneous and shows size effects, characteristic of a porous catalyst. The catalyst can be recycled without losing its framework integrity and catalytic activity. The catalytic activity has been compared with di-Me 2-aminoterephthalate and the isostructural amino-free MOF (UiO-66). The superior performance of UiO-66-NH₂ has been attributed to the site-isolated acid-base bifunctional character. It has been proposed that the Zr site in close proximity to the amino group activates aldehydes to promote the formation of aldimine intermediates from the aldehydes and the amino group. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4SDS of cas: 55490-87-4).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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.SDS of cas: 55490-87-4

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

6-Cyclohexylmethyl-3-hydroxypyrimidine-2,4-dione as an inhibitor scaffold of HIV reverse transcriptase: Impacts of the 3-OH on inhibiting RNase H and polymerase was written by Tang, Jing;Kirby, Karen A.;Huber, Andrew D.;Casey, Mary C.;Ji, Juan;Wilson, Daniel J.;Sarafianos, Stefan G.;Wang, Zhengqiang. And the article was included in European Journal of Medicinal Chemistry in 2017.Recommanded Product: 2-Cyclohexylacetonitrile This article mentions the following:

3-Hydroxypyrimidine-2,4-dione (HPD) represents a versatile chem. core in the design of inhibitors of human immunodeficiency virus (HIV) reverse transcriptase (RT)-associated RNase H and integrase strand transfer (INST). We report herein the design, synthesis and biol. evaluation of an HPD subtype (4, IV) featuring a cyclohexylmethyl group at the C-6 position. Antiviral testing showed that most analogs of 4 inhibited HIV-1 in the low nanomolar to submicromolar range, without cytotoxicity at concentrations up to 100 μM. Biochem., these analogs dually inhibited both the polymerase (pol) and the RNase H functions of RT, but not INST. Co-crystal structure of 4a (IV; R¹ = i-Pr, R² = H) with RT revealed a nonnucleoside RT inhibitor (NNRTI) binding mode. Interestingly, chemotype 11, the synthetic precursor of 4 lacking the 3-OH group, did not inhibit RNase H while potently inhibiting pol. By virtue of the potent antiviral activity and biochem. RNase H inhibition, HPD subtype 4 could provide a viable platform for eventually achieving potent and selective RNase H inhibition through further medicinal chem. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Recommanded Product: 2-Cyclohexylacetonitrile).

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. 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: 2-Cyclohexylacetonitrile

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Nitrile – Wikipedia,
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Organophosphorus compounds with β-cyanoethyl-type structural components. I. Synthesis of β-cyanoethylated amidophosphites and phosphoramides was written by Petrov, Pavel;Vlad, Florin-Iosif;Muresan, Sorel;Valceanu, Radu. And the article was included in Revista de Chimie (Bucharest) in 1996.Product Details of 7528-78-1 This article mentions the following:

This article presents studies performed on obtaining some β-cyanoethylated phosphonamides and phosphoramides, as well as their possible use. Thus, reaction of di-Me phosphite, PCl₃, or POCl₃ with a mixture of NH(CH₂CH₂CN)₂ and N(CH₂CH₂CN)₃ gave (MeO)₂P(O)N(CH₂CH₂CN)₂, P[N(CH₂CH₂CN)₂]₃, or P(O)[N(CH₂CH₂CN)₂]₃, resp. 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. 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.Product Details of 7528-78-1

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Nitrile – Wikipedia,
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Binding interactions and FRET between bovine serum albumin and various phenothiazine-/anthracene-based dyes: a structure-property relationship was written by Bhuin, Shouvik;Halder, Sayantan;Saha, Subit Kumar;Chakravarty, Manab. And the article was included in RSC Advances in 2021.Application of 55490-87-4 This article mentions the following:

The present study demonstrates binding interactions and Forster resonance energy transfer (FRET) between bovine serum albumin (BSA) and a series of structurally and electronically diverse phenothiazine (PTZ) and anthracene (ANT) dyes. Upon selective excitation of tryptophan (Trp) residues of BSA, radiationless energy transfer to a dye takes place, resulting in fluorescence quenching of the former. Fluorescence quenching mechanisms, FRET parameters, possible locations, and binding constants of dyes with the BSA have been examined to deduce a structure-property relationship. The mechanism of quenching is apparently static in nature. PTZ dyes with heteroatoms and a pentyl tail (C5-PTZ) attached to them were found to have a stronger binding affinity with BSA as compared to ANT dyes. Stronger binding affinities of C5-PTZ dyes with BSA result in greater energy transfer efficiencies (ET). A dye with a strong electron-withdrawing group present in it has shown better energy accepting capability. A FRET study with dicyanoaniline (DCA) analogs of PTZ and ANT dyes (C5-PTZDCA and ANTDCA, resp.) revealed that ET depends on electronic and structural factors of mols. An almost orthogonal geometry between ANT and DCA moieties (�9°) in ANTDCA induces the greater extent of electron transfer from ANT to DCA, showing a higher ET for this dye as compared to C5-PTZDCA in which the torsion angle is only �8°. Further, the observed facts have been validated by exptl. determined bandgaps (using cyclic voltammetry experiments) for all the dyes. Thus, the hydrophobic character and the presence of interactive substituents along with the electron-accepting abilities majorly control the FRET for such dyes with BSA. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Application of 55490-87-4).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) belongs to nitriles. Nitrile carbon shifts are in the range of 115�25 ppm whereas in isonitriles the shifts are around 155�65 ppm. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Application of 55490-87-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts