Category: nitriles-buliding-blocks

Highly selective chemodosimeter for cyanide based on a doubly activated Michael acceptor type of coumarin thiazole fluorophore was written by Park, Seokan;Kim, Hae-Jo. And the article was included in Sensors and Actuators, B: Chemical in 2012.Recommanded Product: 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile This article mentions the following:

A doubly activated Michael acceptor type of coumarin thiazole fluorophore (1) was prepared and applied for the detection of cyanide ions in aqueous solution The chemodosimeter exhibited a highly selective and sensitive response to cyanide over other various anions through the Michael addition of cyanide to 1. Upon the addition of cyanide ions, the apparent color and fluorescence changes of 1 were observable with a detection limit of 2.3 μM of the cyanide anions in aqueous solution In the experiment, the researchers used many compounds, for example, 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6Recommanded Product: 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. 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: 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Discovery of Tetrasubstituted Imidazolines as Potent and Selective Neuropeptide Y Y5 Receptor Antagonists: Reduced Human Ether-a-go-go Related Gene Potassium Channel Binding Affinity and Potent Antiobesity Effect was written by Sato, Nagaaki;Ando, Makoto;Ishikawa, Shiho;Jitsuoka, Makoto;Nagai, Keita;Takahashi, Hirobumi;Sakuraba, Aya;Tsuge, Hiroyasu;Kitazawa, Hidefumi;Iwaasa, Hisashi;Mashiko, Satoshi;Gomori, Akira;Moriya, Ryuichi;Fujino, Naoko;Ohe, Tomoyuki;Ishihara, Akane;Kanatani, Akio;Fukami, Takehiro. And the article was included in Journal of Medicinal Chemistry in 2009.Name: 4-methoxypicolinonitrile This article mentions the following:

A series of novel imidazoline derivatives was synthesized and evaluated as neuropeptide Y (NPY) Y5 receptor antagonists. Optimization of previously reported imidazoline leads, I and II, was attempted by introduction of substituents at the 5-position on the imidazoline ring and modification of the bis(4-fluorophenyl) moiety. A number of potent derivatives without human ether-a-go-go related gene potassium channel (hERG) activity were identified. Selected compounds, including III, were shown to have excellent brain and CSF permeability. Compound III displayed a suitable pharmacokinetic profile for chronic in vivo studies and potently inhibited D-Trp³⁴NPY-induced acute food intake in rats. Oral administration of III resulted in a potent reduction of body weight in a diet-induced obese mouse model. In the experiment, the researchers used many compounds, for example, 4-methoxypicolinonitrile (cas: 36057-44-0Name: 4-methoxypicolinonitrile).

4-methoxypicolinonitrile (cas: 36057-44-0) 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. 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.Name: 4-methoxypicolinonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

One-Pot Preparation of C₁-Homologated Aliphatic Nitriles from Aldehydes through a Wittig Reaction under Metal-Cyanide-Free Conditions was written by Ezawa, Masatoshi;Togo, Hideo. And the article was included in European Journal of Organic Chemistry in 2017.Synthetic Route of C8H13N This article mentions the following:

A one-pot protocol to obtain C₁-homologated aliphatic nitriles was achieved by treating aromatic and aliphatic aldehydes with the (methoxymethyl)triphenylphosphonium ylide followed by hydrolysis of the resulting Me vinyl ethers with pTsOH (Ts = para-toluenesulfonyl) and treatment with mol. iodine and aqueous ammonia under metal cyanide free conditions. Neopentyl-type nitriles, which could not be obtained by conventional methods that involved conversion of the neopentyl alc. into a tosylate and treatment with metal cyanide, were successfully obtained by using the present method. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Synthetic Route of C8H13N).

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.Synthetic Route of C8H13N

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electrospinning NH₂-MIL-101/PAN nanofiber mats: A promising catalyst with Lewis acidic and basic bifunctional sites for organic transformation reactions was written by Hassan, Hassan M. A.;Alhumaimess, Mosaed S.;Kamel, Mahmoud M.;Alsohaimi, Ibrahim H.;Aljaddua, Huda I.;Aldosari, Obaid F.;Algamdi, Mohammad. S.;Mohamed, Rasha M. K.;El-Aassar, M. R.. And the article was included in Colloids and Surfaces, A: Physicochemical and Engineering Aspects in 2022.Safety of 2-(Anthracen-9-ylmethylene)malononitrile This article mentions the following:

Because of their distinctive characteristics, like great surface area and capability of structure modifications, Metal-organic frameworks (MOFs) were endorsed as outstanding candidates for catalysis purposes. The incorporation of MOF into an organic polymer frameworks is thought to be a promising approach to enhance the catalysts performance, however, a facile and low-cost approach to prepare such catalysts is currently missing. Herein, a direct approach for integration the MOF into nanofibers with improved catalytic organic transformation reactions without film rupture is reported. The electrospun NH₂-MIL-101 @polyacrylonitrile (PAN) catalyst nanofibers with varied MOF to PAN mass ratio was fabricated by a facile electrospinning approach and used as integrated catalyst for Friedel-Crafts acylation of anisole, esterification of amyl alc., and Knoveonagel condensation reaction of aldehydes. The fabricated MOF-catalysts nanofibers NH₂-MIL-101 @PAN show effective anisole acylation, ester production, and Knoveonagel condensation reaction. The anisole acylation, ester production, and Knoveonagel condensation efficiency boosted to 90%, 79%, and 98% after incorporating NH₂-MIL-101 nanocrystals into the elctrospun PAN nanofibers. The great surface area, available active centers in the pore architecture, and unsaturated Cr³⁺ Lewis acid centers are responsible for this exceptional performance. Because of its adaptability, our approach offers a cutting-edge and intriguing platform for the future tailoring of MOF fabrics with a wide range of practical uses. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Safety of 2-(Anthracen-9-ylmethylene)malononitrile).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. 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.Safety of 2-(Anthracen-9-ylmethylene)malononitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Solar thermochemical reactions. Part II. Synthesis of 2-aminothiophenes via Gewald reaction induced by solar thermal energy was written by Mekheimer, Ramadan Ahmed;Ameen, Mohamed Abdallah;Sadek, Kamal Usef. And the article was included in Chinese Chemical Letters in 2008.Name: 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile This article mentions the following:

Green conditions were developed for the synthesis of substituted 2-aminothiophenes employing multicomponent reactions of a ketone with active methylene nitrile and elemental sulfur induced by free solar thermal energy. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Name: 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. 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.Name: 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

De novo synthesis of bifunctional conjugated microporous polymers for synergistic coordination mediated uranium entrapment was written by Yu, Boxuan;Zhang, Lei;Ye, Gang;Liu, Qingzhi;Li, Jiongli;Wang, Xudong;Chen, Jing;Xu, Shengming;Ma, Shengqian. And the article was included in Nano Research in 2021.Formula: C7H4Br2N2 This article mentions the following:

This work reports a de novo synthesis of novel bifunctional conjugated microporous polymers (CMPs) exhibiting a synergistic-effect involved coordination behavior to uranium. It is highlighted that the synthetic strategy enables the engineering of the coordination environment within amidoxime functionalized CMP frameworks by specifically introducing ortho-substituted amino functionalities, enhancing the affinity to uranyl ions via forming synergistic complexes. The CMPs exhibit high Brunauer-Emmett-Teller (BET) surface area, well-developed three-dimensional (3D) networks with hierarchical porosity, and favorable chem. and thermal stability because of the covalently cross-linked structure. Compared with the amino-free counterparts, the adsorption capacity of bifunctional CMPs was increased by almost 70%, from 105 to 174 mg/g, indicating evidently enhanced binding ability to uranium. Moreover, new insights into coordination mechanism were obtained by in-depth XPS anal. and d. functional theory (DFT) calculation, suggesting a dominant role of the oxime ligands forming a 1:1 metal ions/ligands (M/L) coordination model with uranyl ions while demonstrating the synergistic engagement of the amino functionalities via direct binding to uranium center and hydrogen-bonding involved secondary-sphere interaction. This work sheds light on the underlying principles of ortho-substituted functionalities directed synergistic effect to promote the coordination of amidoxime with uranyl ions. And the synthetic strategy established here would enable the task-specific development of more novel CMP-based functional materials for broadened applications. In the experiment, the researchers used many compounds, for example, 2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5Formula: C7H4Br2N2).

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. 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: C7H4Br2N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A recyclable Cu/Al-HT catalyst for amination of aryl chlorides was written by Likhar, Pravin R.;Arundhathi, R.;Kantam, M. Lakshmi. And the article was included in Tetrahedron Letters in 2007.COA of Formula: C14H12N2 This article mentions the following:

A simple Cu/Al-HT catalyzed amination of aryl chlorides with primary and secondary aromatic amines was developed. This ligand-free heterogeneous Cu/Al-HT catalyst, in conjunction with base, also efficiently works for the amination of aryl chlorides with cycloalkyl amines. This method tolerates a variety of functional groups and does not require an expensive additive. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3COA of Formula: C14H12N2).

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. 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: C14H12N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Spectroscopic behavior of anthracene substituted by dicyanovinyl in different positions was written by Wang, Hua;Zhang, Baowen;Cao, Yi;Xu, Li. And the article was included in Huaxue Yanjiu in 1997.Electric Literature of C18H10N2 This article mentions the following:

Two conjugating electron donor-acceptor (D-A) compounds, 2-dicyanovinyl anthracene(2-DCVA) and 9-dicyanovinyl anthracene(9-DCVA), were synthesized and their spectroscopic properties in a series of solvents with different polarity and at different temperatures were studied. The results reveal that both compounds show intramol. charge transfer (ICT) state emission at different polarity of solvents and the fluorescence quantum yield (Φ_F) of 2-DCVA is much higher than that of 9-DCVA, due to that the structure of 2-DCVA is more planar than 9-DCVA. The dipole moment differences between excited states and ground states of the both compounds were estimated by the formula of Bilot-Kawski. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Electric Literature of C18H10N2).

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. 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.Electric Literature of C18H10N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Calcined Mg-Al hydrotalcite as a heterogeneous base catalyst for Gewald aminothiophene synthesis was written by Rajagopal, R.;Jyothi, T. M.;Daniel, Thomas;Srinivasan, K. V.;Rao, B. S.. And the article was included in Synthetic Communications in 2001.COA of Formula: C8H8N2S This article mentions the following:

Calcined Mg-Al hydrotalcite (Mg/Al=4) has been conveniently employed as a heterogeneous base catalyst in the synthesis of 2-amino-3-cyanothiophenes adopting a one pot Gewald aminothiophene methodol. The compounds thus prepared included 2-amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile, 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrile, 2-amino-3-cyano-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene and 2-amino-4,5-dimethyl-3-thiophenecarbonitrile. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2COA of Formula: C8H8N2S).

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. 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.COA of Formula: C8H8N2S

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Use of the least squares method for estimating the sorption capability of cyano-group-containing phases in gas chromatography was written by Zakirov, N. S.. And the article was included in Zhurnal Analiticheskoi Khimii in 1987.Formula: C9H12N4 This article mentions the following:

The least squares method was used for quant. estimation of the sorption capability of cyano-group containing stationary phases in gas chromatog. separation of alcs., nitriles, and hydrocarbons. The method can be used for selection and optimization of stationary phases with respect to analyte chain length. In the experiment, the researchers used many compounds, for example, 3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1Formula: C9H12N4).

3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1) 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.Formula: C9H12N4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts