Nitriles-buliding-blocks

Contribution to our Knowledge of the Terpenes and the Ethereal Oils. 91st Paper. (C) The Behavior of β-Cyclohexylethylamine toward Nitrous Acid was written by Wallach, O.. And the article was included in Justus Liebigs Annalen der Chemie in 1908.SDS of cas: 4435-14-7 This article mentions the following:

(Cf. Ibid.). Cyclohexylacetonitrile, b. 215°, [n]_D¹⁸ 1.4575 prepared from the amide of cyclohexylacetic acid, on reduction, yielded β-cyclohexylethylamine, b. 188-9°, [n]_D¹⁹ 1.4647. With HNO₂, the latter did not form a 7-ring system, but a little cyclohexylethylene, b. 132-7°, and the alcohols C₆H₁₁.CH₂.CH₂OH and. C₆H₁₁.CH(OH).Me, which were separated by oxidation with chromic acid and formation of semicarbazones. In this way, cyclohexylacetaldehyde, semicarbazone, m. 132-4°, and cyclohexylmethylketone, semicarbazone, m. 172-3°, were obtained, while the acids formed in the oxidation were found to be cyclohexylacetic and adipic acids. 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. 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.SDS of cas: 4435-14-7

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Nitrile – Wikipedia,
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One-pot synthesis of secondary amines from alcohols and nitroarenes on TiO₂ loaded with Pd nanoparticles under UV irradiation was written by Selvam, Kaliyamoorthy;Sakamoto, Hirokatsu;Shiraishi, Yasuhiro;Hirai, Takayuki. And the article was included in New Journal of Chemistry in 2015.Product Details of 10282-32-3 This article mentions the following:

Photoirradiation (λ > 300 nm) of TiO₂ loaded with Pd nanoparticles (2%, ∼5 nm diameter) in water containing benzyl alc. and nitrobenzene at room temperature successfully produces the corresponding secondary amine (N-benzylaniline) with 96% yield. This is achieved via three consecutive catalytic reactions: (i) photocatalytic oxidation of alc. (aldehyde formation) and reduction of nitrobenzene (aniline formation); (ii) catalytic condensation of the formed aldehyde with aniline on the TiO₂ surface (imine formation); and, (iii) photocatalytic hydrogenation of the formed imine (secondary amine formation). This catalytic system successfully produces several kinds of secondary amines, even those containing reducible substituents such as -CN, -COOH, or -CHO with >76% yields. 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 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).Product Details of 10282-32-3

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Synthesis of 4-aminothieno[2,3-b]pyridine-5-carboxylic acids was written by Lalezari, Iradj. And the article was included in Journal of Heterocyclic Chemistry in 1979.Recommanded Product: 70291-62-2 This article mentions the following:

The title compounds I [R = R¹ = Me or RR¹ = (CH₂)_n, n = 3,4,5] were prepared in ∼80% yields by condensing 2-amino-3-cyanothiophenes with Et 3-aminocrotonate in the presence of p-MeC₆H₄SO₃H, EtONa-catalyzed cyclization of the resulting II, and hydrolysis. 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: 70291-62-2).

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 115–125 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).Recommanded Product: 70291-62-2

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Nitrile – Wikipedia,
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4-(Tetrazolylalkyl)piperidine-2-carboxylic acids. Potent and selective N-methyl-D-aspartic acid receptor antagonists with a short duration of action was written by Ornstein, Paul L.;Schoepp, Darryle D.;Arnold, M. Brian;Leander, J. David;Lodge, David;Paschal, Jonathan W.;Elzey, Tom. And the article was included in Journal of Medicinal Chemistry in 1991.Formula: C7H6N2O This article mentions the following:

A series of trans– and cis-4-(tetrazolylalkyl)piperidine-2-carboxylic acids I (R = H, Me) and II (n = 1, R = H, Me; n = 2-4, R = H) as potent and selective N-methyl-D-aspartic acid (NMDA) receptor antagonists were prepared and evaluated in vitro in both receptor binding assays and in a cortical-wedge preparation to determine affinity, potency, and selectivity. The new amino acids were also evaluated in vivo for their ability to block NMDA-induced convulsions in neonatal rats and NMDA-induced lethality in mice. The most potent compound of this series was I (R = H). I (R = H) blocked both NMDA-induced convulsions in neonatal rats and NMDA-induced lethality in mice. This is the first example of an NMDA receptor antagonist that incorporates a tetrazole moiety as an ω-acid bioisostere. These amino acid antagonists are also unique from their phosphonic acid counterparts in that they have a shorter duration of action in vivo. In the experiment, the researchers used many compounds, for example, 4-methoxypicolinonitrile (cas: 36057-44-0Formula: C7H6N2O).

4-methoxypicolinonitrile (cas: 36057-44-0) 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.Formula: C7H6N2O

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Spectrographic method for the detection of active methylene groups and synthesis of several styrene and stilbene derivatives. VI. Amino derivatives of phenylacetonitrile was written by Boyer, Jacqueline;Bruylants, Albert. And the article was included in Bulletin de la Societe Chimique de France in 1958.Product Details of 67197-53-9 This article mentions the following:

The reactivity of m- and p-amino derivatives of PhCH₂CN in condensations with BzH and its p-NMe₂ derivative decreases with decreasing acidity of the CH₂CN group. The order of acidity produced by the following substituents in PhCH₂CN, as determined by comparison of spectra in EtOH and EtONa, is: H ∼ p-Me₃NI ∼ m-Me₃NI ≫ p-NH₂ > m-NH₂ > p-Me₂N ≫ m-Me₂N. Changes in spectra with time in EtONa show that the ionization of the last four of these is slow. The m- and p-NH₂ derivatives react with BzH and p-Me₂NC₆H₄CHO to yield principally the azomethines, but the other compounds give high yields of α-cyanostilbenes after 40 hrs. in alc. EtONa. The following cyanostilbenes, XC₆H₄C(CN):CHC₆H₄Y, were obtained (X, Y, yield, and m.p. are given): p-Me₃NI, H, 85, 175-98° (geometric isomers); p-Me₃NI, p-NMe₂, 87, 195-6.5°; p-Me₂N, H, 87, 136-7°; p-Me₂N, p-NMe₂, 85, 196-7.5°; m-Me₃NI, H, 88, 172-97° (geometric isomers); m-Me₃NI, p-NMe₂, 92, 161-2°; m-Me₂N, H, 90, -; m-Me₂N, p-NMe₂, 88, 117-208°. The p-H₂NC₆H₄CH₂CN and its m-isomer, b₈ 179-80° (HCl salt, m. 199-201°), were prepared by reduction of the corresponding nitro compounds with SnCl₂, quaternized with MeI to the p-Me₃NI, m. 167-8°, and m-Me₃NI, m. 173-4°, derivatives resp., and these were demethylated to p-Me₂NC₆H₄CH₂CN, m. 53.5-55°, and its m-isomer, m. 173-4°, resp. In the experiment, the researchers used many compounds, for example, 2-(2,6-Dibromophenyl)acetonitrile (cas: 67197-53-9Product Details of 67197-53-9).

2-(2,6-Dibromophenyl)acetonitrile (cas: 67197-53-9) 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. Product Details of 67197-53-9

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Nitrile – Wikipedia,
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Engineering a Nanoscale Primary Amide-Functionalized 2D Coordination Polymer as an Efficient and Recyclable Heterogeneous Catalyst for the Knoevenagel Condensation Reaction was written by Markad, Datta;Khullar, Sadhika;Mandal, Sanjay K.. And the article was included in ACS Applied Nano Materials in 2018.Related Products of 55490-87-4 This article mentions the following:

This work reports the design, structural characterization and catalytic behavior of the first example of primary amide- functionalized coordination polymers (CPs), namely {[Cd₂(2-bpbg)(fum)₂(H₂O)₂]·8.5H₂O}_n (1) (where, 2-bpbg = N,N’-bis(2-pyridylmethyl)-1,4-diaminobutane-N,N’-diacetamide and fum = fumarate). CP 1 was synthesized from a one-pot self-assembly of starting materials in methanol under ambient conditions in excellent yield and purity, allowing an easy access to multi-gram quantities of it within few hours. As an example, CP 1 has been used as a highly efficient heterogeneous catalyst in the carbon-carbon bond forming Knoevenagel condensation reaction for the conversion of benzaldehyde to benzylidene malononitrile. CP 1 possesses both Lewis acidic and Bronsted basic character for the presence of unsaturated metal sites and primary amide groups, resp., making it a highly competent bifunctional catalyst for such type of reactions. Surprisingly, 100% conversion was observed using only 2 mol% catalyst within 1 h at 27° in methanol. However, 2 mol% and 3 mol% catalyst loadings but without a solvent gives 93% and 100% conversions, resp., in 1 h at 27°. CP 1 is far better than those reported in the literature so far. To prove the uniqueness and efficiency of the primary amide based ligand, a similar compound with a pyridyl-based ligand was also synthesized, {[Cd₂(tpbn)(fum)₂]·6H₂O}_n (2) (where, tpbn = N’,N’,N”,N”-tetrakis(pyridin-2-ylmethyl)butane-1,4-diamine). Using CP 2 under the same catalyst loading and conditions (2 mol%, 27°, 1 h), only 28% conversion was observed Selective heterogeneous catalytic properties of 1 over 2 are due to the presence of the primary amide moieties and open metal sites. Moreover, CP 1 can easily be separated from the reaction mixture and reused for five consecutive cycles without significant loss of its activity. Both 1 and 2 were fully characterized by elemental anal., IR spectroscopy, TGA and single crystal and powder x-ray diffraction. These crystallize in the triclinic P1 space group, showing their isostructural nature and 3-connected, uninodal {63}-hcb net topol. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Related Products of 55490-87-4).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) 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. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Related Products of 55490-87-4

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Base-Mediated Amination of Alcohols Using Amidines was written by Zhang, Chunyan;Li, Zehua;Chen, Jianbin;Qi, Shuo;Fang, Yanchen;Zhang, Sheng;Ren, Chaoyu;Lu, Fenghong;Liang, Zuyu;Jiang, Shaohua;Jia, Xiaofei;Yu, Shuangming;Zhang, Guoying. And the article was included in Journal of Organic Chemistry in 2020.Synthetic Route of C14H12N2 This article mentions the following:

Novel and efficient base-mediated N-alkylation and amidation of amidines with alcs. have been developed, which can be carried out in one-pot reaction conditions, which allows for the synthesis of a wide range of N-alkyl amines and free amides in good to excellent yields with high atom economy. In contrast to borrowing hydrogen/hydrogen autotransfer or oxidative-type N-alkylation reactions, in which alcs. are activated by transition-metal-catalyzed or oxidative aerobic dehydrogenation, the use of amidines provides an effective surrogate of amines. This circumvents the inherent necessity in N-alkylation of an oxidant or a catalyst to be stabilized by ligands. 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. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Synthetic Route of C14H12N2

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Nitrile – Wikipedia,
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Polystyrene-Supported Palladium (Pd@PS)-Catalyzed Carbonylative Annulation of Aryl Iodides Using Oxalic Acid as a Sustainable CO Source for the Synthesis of 2-Aryl Quinazolinones was written by Ram, Shankar;Shaifali;Chauhan, Arvind Singh;Sheetal;Sharma, Ajay Kumar;Das, Pralay. And the article was included in Chemistry – A European Journal in 2019.Reference of 1483-54-1 This article mentions the following:

An efficient and convenient strategy for the synthesis of diversely substituted quinazolinones from o-carbamoyl/cyano aniline and aryl iodides using oxalic acid as a CO source under polystyrene supported palladium (Pd@PS) nanoparticles (NPs) catalyzed conditions was developed. The oxalic acid were employed as safe, economic, environmentally benign, sustainable and bench-stable, solid CO surrogate under Double-Layer-Vial (DLV) system for the synthesis of 2-aryl quinazolinones. This methodol. does not require any special high-pressure equipment like autoclaves, microwaves, etc. Moreover, a simple procedure for catalyst preparation, catalyst recyclability, easy handling of reaction, additive and base-free generation of CO, excellent to good yields and vast substrate scope were the addnl. features of developed protocol. In the experiment, the researchers used many compounds, for example, 2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1Reference of 1483-54-1).

2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1) 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.Reference of 1483-54-1

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The comparison of molecular surfaces by neural networks and its applications to quantitative structure activity studies was written by Polanski, Jaroslaw;Gasteiger, Johann;Wagener, Markus;Sadowski, Jens. And the article was included in Quantitative Structure-Activity Relationships in 1998.Application In Synthesis of 3-Amino-4-methoxybenzonitrile This article mentions the following:

Self-organizing Kohonen neural networks are used to obtain quant. structure-activity relationships. Simple mols. were selected to discuss the essential features of the transformation. Descriptors calculated from maps obtained from comparative studies with template mols. applied to the anal. of compounds derived from butane, as well as Et carboxylates and nitroanilines and aminobenzonitriles (sweet-tasting compounds) can be correlated with various mol. effects. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methoxybenzonitrile (cas: 60979-25-1Application In Synthesis of 3-Amino-4-methoxybenzonitrile).

3-Amino-4-methoxybenzonitrile (cas: 60979-25-1) 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. 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-Amino-4-methoxybenzonitrile

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Nitrile – Wikipedia,
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Silica-sulfuric acid: novel, simple, efficient and reusable catalyst for hydration of nitrile to amide was written by Chandrashekharappa, Sandeep;Venugopala, Katharigatta N.;Venugopala, Rashmi;Odhav, Bharti. And the article was included in Asian Journal of Chemistry in 2016.Reference of 60979-25-1 This article mentions the following:

Silica-sulfuric acid efficiently catalyzes conversion of aliphatic, substituted aromatic and hetero aromatic nitriles to their corresponding amides in good to excellent yields under reflux condition. Products obtained were purified by column chromatog. method and characterized by ¹H NMR, ¹³C NMR and mass spectral anal. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methoxybenzonitrile (cas: 60979-25-1Reference of 60979-25-1).

3-Amino-4-methoxybenzonitrile (cas: 60979-25-1) 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.Reference of 60979-25-1

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts