Category: nitriles-buliding-blocks

Studies on the in vitro hepatic microsomal formation of amides during the metabolism of certain secondary and tertiary benzylic amines was written by Ulgen, M.;Gorrod, J. W.. And the article was included in European Journal of Drug Metabolism and Pharmacokinetics in 2000.Name: 4-(Benzylamino)benzonitrile This article mentions the following:

A review with 21 references Part of our interest during the last few years has been to investigate the possible intermediate(s) and mechanism(s) involved in the formation of amides from N-benzylic amines. A number of benzylic amines with different aryl and alkyl moieties introduced onto the constituent nitrogen were prepared, thus creating a wide variety of secondary, tertiary and heterocyclic benzylic amines with different logP and pKa characteristics (Tables I & II). In some experiments, the possible intermediates of this reaction, i.e. nitrones (Table III), imines (Table IV) and amides themselves (Table V), were used as substrates in our metabolic studies. Their in vitro hepatic microsomal metabolism was studied in order to obtain a structure/metabolic activity relationship for the formation of amides from benzylic amines. This communication reviews these studies and reports our conclusions as to the mechanism of formation of amides from N-benzylic amines. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Name: 4-(Benzylamino)benzonitrile).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) 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. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Name: 4-(Benzylamino)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Studies on monolayers. 1. Surface tension and absorption spectroscopic measurements of monolayers of surface-active azo and stilbene dyes was written by Heesemann, Juergen. And the article was included in Journal of the American Chemical Society in 1980.Formula: C8H6N2O2 This article mentions the following:

In order to develop new mols. as functional components of monolayer assemblies a series of 9 surface-active azo and stilbene compounds were synthesized. Their monolayer properties at the air-water interface were studied by surface pressure-surface area measurements and spectroscopic techniques. Small changes in the mol. structure of the surfactants (such as length of the fatty acid chain, type of the chromophore, etc.) have an immense influence on the monolayer properties. For monolayers of some of the dyes, van der Waals-like isotherms are obtained, which show a liquid expanded state, a phase transition region, and a condensed state. Monolayer absorbance spectra show that in the liquid expanded state at 100-110 Ų/mol. the chromophores lie flatly on the water surface, forming monomers. Surface absorbance-surface area isotherms show that the phase transition region of the isotherms can be assigned to a change of orientation of the chromophore axis (horizontal → vertical) and an aggregation of the chromophores (monomers → H aggregates). High dichroic and narrow absorbance bands are observed for condensed films of several dyes, which are assigned to H aggregates (planar pincushion-like arrangement of the chromophores). By means of mol. models several mol. arrangements are discussed which are consistent with the exptl. results. Numerous synthetic intermediates are included in the present paper. In the experiment, the researchers used many compounds, for example, 5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6Formula: C8H6N2O2).

5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6) 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. 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. Formula: C8H6N2O2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

N-Alkylation of Amines with Alcohols Catalyzed by a Water-Soluble Cp^*Iridium Complex: An Efficient Method for the Synthesis of Amines in Aqueous Media was written by Kawahara, Ryoko;Fujita, Ken-ichi;Yamaguchi, Ryohei. And the article was included in Advanced Synthesis & Catalysis in 2011.Product Details of 10282-32-3 This article mentions the following:

An efficient and environmentally benign catalytic system for the synthesis of various organic amines catalyzed by the water-soluble and air-stable (pentamethylcyclopentadienyl)-iridium-ammine iodide complex, [Cp^*Ir(NH₃)₃][I^–]₂, has been developed. A wide variety of secondary and tertiary amines were synthesized by the N-alkylation reactions of theor. equivalent of amines with alcs. in water under air without a base. The synthesis of cyclic amines was also achieved by the N-alkylation of benzylamine with diols. Furthermore, recycling of the present water-soluble Cp^*Ir catalyst was accomplished. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Product Details of 10282-32-3).

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. 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. Product Details of 10282-32-3

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Nitrile – Wikipedia,
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Synthesis of Densely Substituted Pyridine Derivatives from 1-Methyl-1,3-(ar)enynes and Nitriles by a Formal [4+2] Cycloaddition Reaction was written by He, Dandan;Wang, Bowen;Duan, Kanghui;Zhou, Yang;Li, Meng;Jiang, Huanfeng;Wu, Wanqing. And the article was included in Organic Letters in 2022.Application In Synthesis of 3-(tert-Butyl)benzonitrile This article mentions the following:

An attractive method for assembling densely substituted pyridine derivatives I [R = Ph, 4-MeC₆H₄, 2-naphthyl, etc.; R¹ = H, 6-Me, 6-Ph, 7-Ph, 8-F; R² = H, Me, CN, Ph; R³ = Ph, 4-FC₆H₄, 2-pyridyl, etc.], II [R⁴ = Ph, 4-MeOC₆H₄, 3-ClC₆H₄, etc.; R⁵ = Ph, 2-naphthyl, 2-pyridyl, etc.; Y = O, S], III [R⁶ = H, 3-Me, 4-MeO, etc.] from 1-methyl-1,3-(ar)enynes and nitriles via a formal [4+2] cycloaddition had been established. The well-balanced affinities of two alkali metal salts enabled C(sp³)-H bond activation and excellent chemo- and regioselectivities. Exptl. studies revealed that nitrile functioned only as a partial nitrogen source for pyridine synthesis, and the addition of a metalated imine intermediate to an intramol. alkyne was the rate-limiting step. In the experiment, the researchers used many compounds, for example, 3-(tert-Butyl)benzonitrile (cas: 154532-34-0Application In Synthesis of 3-(tert-Butyl)benzonitrile).

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. 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.Application In Synthesis of 3-(tert-Butyl)benzonitrile

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Metal-free catalysis of the reductive amination of aldehydes using a phosphonium-doped porous aromatic framework was written by You, Bingxin;Zou, Min;Xu, Ruitong;Tian, Yuyang;Wang, Baolin;Zhu, Guangshan. And the article was included in Molecular Catalysis in 2022.Name: 4-(Benzylamino)benzonitrile This article mentions the following:

In this study, OTf@PAF-180, a porous aromatic framework (PAF) containing rich Lewis acidic phosphonium centers and triflate (-OTf) counter anions, was prepared via Yamamoto-type Ullmann cross-coupling of tris(4-bromophenyl)phosphane and subsequent treatment with Me triflate (MeOTf). It showed high performance in catalyzing the reductive amination of aldehydes using dimethylphenylsilane (PhMe₂SiH) as the hydride source, and a variety of amines were prepared in this way with good to excellent yields. As a metal-free heterogeneous catalyst, OTf@PAF-180 also exhibited excellent recyclability and retained high catalytic activity after five consecutive cycles. The high activity, recyclability and stability of OTf@PAF-180 made it a promising novel heterogeneous catalyst for organic synthesis. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Name: 4-(Benzylamino)benzonitrile).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) 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.Name: 4-(Benzylamino)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A simple triazine (D-A) based organic fluorophore selective dual sensor for Copper(II) and dichromate ions and its solvatochromism, solid state sensing, logic gate applications was written by Harikrishnan, Muniyasamy;Sadhasivam, Velu;Mariyappan, Mathappan;Murugesan, Sepperumal;Malini, Nelson;Siva, Ayyanar. And the article was included in Dyes and Pigments in 2019.Name: 4-(Ethylamino)benzonitrile This article mentions the following:

Herein, the design and synthesis of triazine based fluorophore for selective dual sensing of copper(II) and dichromate ions in non-aqueous solution has been reported. The triazine based fluorophore (TZAS) was synthesized in very good yield from inexpensive starting materials. The fluorophore has been thoroughly characterized by various spectral techniques. The TZAS has N-(ethyl)amine and triazine core which are acting as donor and acceptor, resp. Further, its interaction with various analytes in both solid and solution phases are studied. The TZAS compound shows pos. solvatochromism upon increasing the solvent polarity from non-polar to polar solvent. The sensing ability of TZAS has been studied against various analytes (cations and anions). The results indicated that the detection limits for dichromate and copper ions in dimethylsulfoxide solvent medium are 1.3 × 10^-8 M and 11 × 10^-8 M resp. The sensing mechanism of the proposed probe in the presence of the Cu²⁺/Cr₂O^2-₇ were determined by the support of NMR, ESI-MS, FTIR spectra, Job’s plot and d. functional theory. Furthermore, the energy gap between frontier orbitals of TZAS and TZAS-analyte calculated through theor. (DFT) anal. The sensing performance of the TZAS is also examined in a logic circuit. This is the first dual coupled sensor of copper(II) cation and dichromate anion by organic fluorophore material. In the experiment, the researchers used many compounds, for example, 4-(Ethylamino)benzonitrile (cas: 4714-63-0Name: 4-(Ethylamino)benzonitrile).

4-(Ethylamino)benzonitrile (cas: 4714-63-0) 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. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Name: 4-(Ethylamino)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Convenient synthesis of disubstituted tacrine derivatives via electrophilic and copper induced reactions was written by Ekiz, Makbule;Tutar, Ahmet;Okten, Salih. And the article was included in Tetrahedron in 2016.Application of 68385-95-5 This article mentions the following:

The bromination of 2-aminobenzonitrile with mol. bromine (2 equiv) furnished 2-amino-3,5-dibromobenzonitrile in 98% yield. One-pot syntheses are described for dibromotacrine derivatives, e.g., I (Y = CH₂), utilizing Friedlander reactions. A convenient route is described for disubstituted derivatives of tacrines from dibromotacrine I (Y = CH₂, CH₂CH₂) (II) by various substitution reactions. Several disubstituted tacrines were synthesized by treatment of II with n-BuLi followed by trapping with an electrophile [Si(Me)₃Cl, S₂(Me)₂]. Both were converted to the corresponding cyano derivatives III (X = Br, Y = CH₂; X = CN, Y = CH₂; X = CN, CH₂CH₂) via copper-assisted nucleophilic substitution reactions in moderate yields (30%, 50%, and 60%, resp.). Copper-induced nucleophilic substitution of dibromide II (Y = CH₂CH₂) with NaOMe afforded mono-methoxide IV in 25% yield. In the experiment, the researchers used many compounds, for example, 2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5Application of 68385-95-5).

2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5) 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 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.Application of 68385-95-5

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis and antimicrobial evaluation of new 4-{[(aryl)methylene]amino}-2-methyl-5,6-substituted thieno[2,3-d]pyrimidines was written by Naresh, K.;Rajeshwar, Y.;Jayaveera, K. N.. And the article was included in World Journal of Pharmacy and Pharmaceutical Sciences in 2014.Application of 70291-62-2 This article mentions the following:

A new series of 4-{[(aryl)methylene]amino}-2-methyl-5,6-substituted thieno[2,3-d]pyrimidines I (R₁R₂ = (CH₂)₃, (CH₂)₅; Ar = C₆H₅, 4-ClC₆H₄, 4-BrC₆H₄, 3-indolyl, etc.) was synthesized by the condensation of 4-amino-2,5,6-substituted theino[2,3-d]pyrimidines II with nine aromatic aldehydes. The compounds were further evaluated for the antibacterial and antifungal activity employing disk diffusion method. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Application of 70291-62-2).

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

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Discovery, Optimization, and in Vivo Evaluation of Benzimidazole Derivatives AM-8508 and AM-9635 as Potent and Selective PI3Kδ Inhibitors was written by Shin, Youngsook;Suchomel, Julia;Cardozo, Mario;Duquette, Jason;He, Xiao;Henne, Kirk;Hu, Yi-Ling;Kelly, Ron C.;McCarter, John;McGee, Lawrence R.;Medina, Julio C.;Metz, Daniela;San Miguel, Tisha;Mohn, Deanna;Tran, Thuy;Vissinga, Christine;Wong, Simon;Wannberg, Sharon;Whittington, Douglas A.;Whoriskey, John;Yu, Gang;Zalameda, Leeanne;Zhang, Xuxia;Cushing, Timothy D.. And the article was included in Journal of Medicinal Chemistry in 2016.COA of Formula: C5H3ClN4 This article mentions the following:

Lead optimization efforts resulted in the discovery of two potent, selective, and orally bioavailable PI3Kδ inhibitors, 1 (AM-8508) and 2 (AM-9635), with good pharmacokinetic properties. The compounds inhibit B cell receptor (BCR)-mediated AKT phosphorylation (pAKT) in PI3Kδ-dependent in vitro cell based assays. These compounds which share a benzimidazole bicycle are effective when administered in vivo at unbound concentrations consistent with their in vitro cell potency as a consequence of improved unbound drug concentration with lower unbound clearance. Furthermore, the compounds demonstrated efficacy in a Keyhole Limpet Hemocyanin (KLH) study in rats, where the blockade of PI3Kδ activity by inhibitors 1 and 2 led to effective inhibition of antigen-specific IgG and IgM formation after immunization with KLH. In the experiment, the researchers used many compounds, for example, 4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4COA of Formula: C5H3ClN4).

4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4) 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. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.COA of Formula: C5H3ClN4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The biological action of malononitriles. I. The effect of substituted malononitriles on the growth of transplanted tumors in mice was written by Gal, Emery M.;Fung, Fung-Haan;Greenberg, David M.. And the article was included in Cancer Research in 1952.Category: nitriles-buliding-blocks This article mentions the following:

The following compounds were prepared and tested for toxicity and effect on sarcoma, carcinoma, and myeloid leukemia in mice; compounds marked *inhibited tumor growth, || slightly promoted tumor growth, † were first synthesized here, ‡ irritated skin and mucous membranes, in each case the substituent on the methylene group of malononitrile is given: 2-(methoxycarboxy)ethyl-, 2-(ethoxycarboxy)ethyl-, 2-cyanoethyl-, methylenebis-, ethylidenebis-, heptylidenebis-, ethoxymethylene- *, aminomethylene-, glyceral- †, citral- †, tiglal- †, furfurylidene-, 5-nitrofurfurylidene- *‡, 2-thenylidene-, 5-nitro-2-thenylidene-, benzylidene- *‡, o-hydroxybenzylidene-, m-hydroxybenzylidene-, p-hydroxybenzylidene- *‡, 2,4-dihydroxybenzylidene-, 3,5-dihydroxybenzylidene-, o-methylbenzylidene- ‡, m-methylbenzylidene-, p-methylbenzylidene-, o-chlorobenzylidene- ‡, p-chlorobenzylidene- *, 2-hydroxy-5-chlorobenzylidene-, 2,4-dichlorobenzylidene-, 2,6-dichlorobenzylidene-, o-nitrobenzylidene- ‡, m-nitrobenzylidene-, p-nitrobenzylidene- *, 2,4-dinitrobenzylidene-, 2,6-dinitrobenzylidene-, 2-chloro-5-nitrobenzylidene ‡, p-methoxybenzylidene-, 2,4-dimethoxybenzylidene-, 2,5-dimethoxybenzylidene-, 3,4-dimethoxybenzylidene-, 3,4,5-trihydroxybenzylidene- †, 3,4,5-trimethoxybenzylidene- †, 3-methoxy-4-hydroxybenzylidene-, piperonal- *, cinnamal-, p-acetamidobenzylidene-, p-dimethylaminobenzylidene-, p-diethylaminobenzylidene-, 1-ethoxy-2-naphthylmethylene-, 9-anthral-, cinchoninal-, α-methylbenzylidene-, 1-methyl-2-(p-chlorophenyl)ethylidene-, 1-methyl-2-cyclopropylethylidene-, 1-methyl-2-(p-fluorophenyl)ethylidene-, 1-methyl-2-(p-methylphenyl)ethylidene-, 1-methyl-2-(p-nitrophenyl)ethylidene- *, 1-propyl-2-phenylethylidene-, 1-methyl-2-furylethylidene- *, 1-methyl-2-thienylethylidene-, isatylphenylazo- ||, p-dimethylaminophenylazo- †||, p-nitrophenylazo- ||, and p-chlorophenylazo- ||. Tested were also 1,3-dimethyl-2,2,4,4-cyclobutanetetranitrile, 2-cyano-1,4-endomethylene-4-cyclohexene ‡, and fumaronitrile. The effects were attributed to the structural properties of the particular compounds rather than to release of cyanide at different rates. Neither NaCN nor malononitrile retarded any of the tumors tested. Toxicity symptoms of the substituted malononitriles were much the same as those described for the parent compound by Heymans and Masoin (Arch. pharmacodynamie 3, 77(1897)). In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Category: nitriles-buliding-blocks).

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. 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.Category: nitriles-buliding-blocks

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts