Category: nitriles-buliding-blocks

Synthesis of tetraethyl ester of 5-aminothiophene by phase transfer catalysis was written by Hu, Kai;Ding, Xiang-Yu;Jia, Xiang-Man;Jiang, Ye;Liu, Feng-Hua. And the article was included in Zhongguo Xiandai Yingyong Yaoxue in 2008.Reference of 58168-20-0 This article mentions the following:

A method for the synthesis of the title compound [i.e., tetra-Et ranelate; 5-[bis(2-ethoxy-2-oxoethyl)amino]-4-cyano-2-(ethoxycarbonyl)-3-thiopheneacetic acid] is reported here. The synthesis of this tetra-Et ester of 5-aminothiophene was achieved by a by phase transfer catalyzed reaction and the best reaction conditions were determined Cyclization of 3-oxopentanedioic acid 1,5-di-Et ester with propanedinitrile and sulfur provided 5-amino-4-cyano-2-(ethoxycarbonyl)-3-thiopheneacetic acid Et ester. Then in acetone, tetra-Et ester of 5-aminothiophene was synthesized from 5-aminothiophene by phase transfer catalysis with Et bromoacetate in presence of a crown ether using potassium carbonate as solid base. Under optimized reaction conditions, crown ether was used as phase transfer catalyst, the molar ratio of alkylating reagent, alkali and reagent was 2.2 and 2.5 resp., the reaction temperature was 60° and the reaction time was 6 h. This method provides high product yield and purity. This is a key intermediate for strontium ranelate (a bone formation stimulant). In the experiment, the researchers used many compounds, for example, Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate (cas: 58168-20-0Reference of 58168-20-0).

Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate (cas: 58168-20-0) 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.Reference of 58168-20-0

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A facile microwave assisted synthesis and anti-inflammatory activity of thiophene[3,2- e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one derivatives was written by Kaur, Rajwinder;Rao, Akkinepally Raghuram;Chadha, Renu;Thakur, Nishant;Goswami, Manish. And the article was included in International Journal of Pharmaceutical Sciences Review and Research in 2016.Category: nitriles-buliding-blocks This article mentions the following:

A series of novel substituted triazolo thieno pyrimidines (5-12) was synthesized by employing innovative synthetic methods. Two methods (A and B) were employed for the synthesis of compounds 3-12. Method B (microwave assisted) was found to be facile, economic and less time consuming compared to conventional method (method A) adopted. The microwave irradiation provided an environment-friendly, remarkable rate of acceleration for the reaction with reduced reaction time and in some cases (under MW irradiation) the yields are also substantially higher. Anti-inflammatory activity and mast cell degranulation studies of synthesized compounds were carried out. Indomethacin was taken as a reference standard in carrageenan induced rat paw edema model for anti-inflammatory studies and in mast cell degranulation studies disodium cromoglycate was used for comparison. All compounds showed a good anti-inflammatory response and mast cell stabilization. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Category: nitriles-buliding-blocks).

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Function-Structure Relationship in Metal-Organic Frameworks for Mild, Green, and Fast Catalytic C-C Bond Formation was written by Razavi, Sayed Ali Akbar;Morsali, Ali. And the article was included in Inorganic Chemistry in 2019.Formula: C18H10N2 This article mentions the following:

Tunability in chem. functionality is a promising characteristic of metal-organic frameworks (MOFs), which plays an important role in developing and improving the practical applications of MOFs. Here, authors applied this important feature of MOFs to be in line with sustainable development and green chem. principles through the synthesis of MOF-based heterogeneous organocatalysts. According to their green functionalization strategy, some isostructural MOFs (azine decorated TMU-4 with the formula [Zn(OBA)(BPDB)_0.5]_n·2DMF, azine-Me functionalized TMU-5 with the formula [Zn(OBA)(BPDH)_0.5]_n·1.5DMF, dihydro-tetrazine decorated TMU-34 with the formula [Zn(OBA)(H₂DPT)_0.5]_n·DMF, and tetrazine functionalized TMU-34(-2H) with the formula [Zn(OBA)(DPT)_0.5]_n·DMF, where H₂OBA = 4,4′-oxybis(benzoic acid), BPDB = 1,4-bis(4-pyridyl)-2,3-diaza-1,3-butadiene, BPDH = 2,5-bis(4-pyridyl)-3,4-diaza-2,4-hexadiene, H₂DPT = 3,6-di(pyridin-4-yl)-1,4-dihydro-1,2,4,5-tetrazine, and DPT = 3,6-di(pyridin-4-yl)-1,2,4,5-tetrazine) have been applied for mild, green, and fast Knoevenagel condensation. These frameworks display different Lewis basic catalytic activities owing to their different functionality and function accessibility. Contrary to extensive articles published about Knoevenagel condensation, this study involves the rare examples in Knoevenagel condensation with such mild conditions (room temperature and atm. pressure) and with a green solution (water as the solvent). Due to the combined synergic effects of the Lewis basicity of TMU-frameworks, the amphoteric and hydrogen bond-participating nature of water mols., maximum conversion times are reached just after 30 min (for TMU-5) and 60 min (for TMU-34). Stability and recyclability tests show that TMU-5 and TMU-34 are completely stable in water at reaction conditions and can retain their crystallinity, porosity, and functionality even after five cycles without any specific reduction in their catalytic conversion. Since, in many cases, amine decorated MOFs are applied in Knoevenagel catalyzed condensation, this study is beneficial in providing information about the effects of azine and tetrazine functional groups in reactant activation and the acceleration of Knoevenagel condensation. In this work, according to green chem. principles and sustainable development, we applied some azine and tetrazine TMU-frameworks as basic heterogeneous organocatalysts for mild, green, and fast Knoevenagel condensation in water at room temperature and atm. pressure. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Formula: C18H10N2).

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. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Formula: C18H10N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis and antiallergy activity of [1,3,4]thiadiazolo[3,2-a]-1,2,3-triazolo[4,5-d]pyrimidin-9(3H)-one derivatives. II. 6-Alkyl- and 6-cycloalkylalkyl derivatives was written by Yokohama, Shuichi;Miwa, Tamotsu;Aibara, Shunzo;Fujiwara, Hiroyuki;Matsumoto, Hiroo;Nakayama, Kiyoshi;Iwamoto, Teiji;Mori, Mikio;Moroi, Reimei. And the article was included in Chemical & Pharmaceutical Bulletin in 1992.Application In Synthesis of 2-Cyclohexylacetonitrile This article mentions the following:

A series of 6-alkyl- or 6-(cycloalkylalkyl)-[1,3,4]thiadiazolo[3,2-a]-1,2,3-triazolo[4,5-d]pyrimidin-9(3H)-ones, including I (R = cyclopentylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclohexylpropyl, cycloheptylethyl, cyclooctylethyl, cyclododecylethyl), was synthesized from the corresponding 1,3,4-thiadiazol-5-amines II and the antiallergic activities of the products were evaluated. Among these compounds 6-(2-cyclohexylethyl)-[1,3,4]thiadiazolo[3,2-a]-1,2,3-triazolo[4,5-d]pyrimidin-9(3H)-one (I, R = cyclohexylethyl), whose x-ray crystallog. stereostructure was determined, is a promising new antiallergic agent, which has low toxicity and dual activity as a leukotriene D₄ receptor antagonist and as an orally active mast cell stabilizer. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Application In Synthesis of 2-Cyclohexylacetonitrile).

2-Cyclohexylacetonitrile (cas: 4435-14-7) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. 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.Application In Synthesis of 2-Cyclohexylacetonitrile

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Nitrile – Wikipedia,
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Activation of elemental sulfur by electrogenerated cyanomethyl anion: synthesis of substituted 2-aminothiophenes by the Gewald reaction was written by Feroci, Marta;Chiarotto, Isabella;Rossi, Leucio;Inesi, Achille. And the article was included in Advanced Synthesis & Catalysis in 2008.Recommanded Product: 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile This article mentions the following:

The activation of elemental sulfur (S₈) has been achieved using the electrogenerated cyanomethyl anion [easily obtained by galvanostatic reduction from acetonitrile/tetraethylammonium hexafluorophosphate (MeCN-Et₄NPF₆)]. The “activated” sulfur reacted with ylidenemalononitriles to give substituted 2-aminothiophenes in very high yields. This variation of the Gewald reaction has been carried out using only catalytic amounts of electricity and supporting electrolyte. A proposed mechanism for the interaction between S₈ and cyanomethyl anion is described. 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. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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.Recommanded Product: 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A new facile route to primary alkanenitriles from terminal alkenes via a hydroboration-cyanation sequence was written by Masuda, Yuzuru;Hoshi, Masayuki;Arase, Akira. And the article was included in Journal of the Chemical Society, Chemical Communications in 1989.Name: 2-Cyclohexylacetonitrile This article mentions the following:

Alkenes R¹CR²:CH₂ (R¹ = alkyl, R² = H or Me) underwent hydroboration with dicyclohexylborane, and treatment of the intermediates with CuCN, Cu(OAc)₂, and cupric acetylacetonate gave R¹CHR²CH₂CN. Methylenecyclopentane of methylenecyclohexane gave the resp. cycloalkaneacetonitriles. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Name: 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. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Name: 2-Cyclohexylacetonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electrochemical Tandem Olefination and Hydrogenation Reaction with Ammonia was written by Zhang, Xiaofeng;Jiang, Runze;Cheng, Xu. And the article was included in Journal of Organic Chemistry in 2021.Safety of 2-Cyclohexylacetonitrile This article mentions the following:

An electrochem. Horner-Wadsworth-Emmons/hydrogenation tandem reaction was achieved using ammonia as electron and proton donors. The reaction could give two-carbon-elongated ester and nitrile from aldehyde or ketones directly. This reaction could proceed with a catalytic amount of base or even without a base. The ammonia provides both the electron and proton for this tandem reaction and enables the catalyst-free hydrogenation of an α,β-unsaturated HWE intermediate. More than 40 examples were reported, and functional groups, including heterocycles and hydroxyl, were tolerated. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Safety of 2-Cyclohexylacetonitrile).

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. 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-Cyclohexylacetonitrile

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

EPR studies of nitrogen-centered free radicals. Part 53. Isolation, EPR spectra and magnetic characterization of N-(arylthio)-2,4-diaryl-6-cyanophenylaminyls was written by Nakatsuji, Masaaki;Miura, Yozo;Teki, Yoshio. And the article was included in Journal of the Chemical Society, Perkin Transactions 2 in 2001.SDS of cas: 68385-95-5 This article mentions the following:

N-(Arylthio)-2,4-diaryl-6-ethoxycarbonylphenylaminyls (1), N-[(2,4-dichlorophenyl)thio]-2,4-diphenyl-6-acetyl-phenylaminyl (2), N-(arylthio)-2,4-diaryl-6-cyanophenylaminyls (3), N-[(2,4-dichlorophenyl)thio]-2,4-bis(4-chloro-phenyl)-6-fluorophenylaminyl (4) and N-[(4-nitrophenyl)thio]-2,4-diphenylphenylaminyl (5) were generated by oxidation of the corresponding N-(arylthio)anilines. Although 4 and 5 were short-lived and decayed in 30 min, 1-3 were quite persistent and 3 could be isolated as radical crystals. EPR spectra were measured for all radicals generated and the spin d. distribution was evaluated. Ab initio MO calculations (the UHF Becke 3LYP/STO 6-31G) were performed, and a quant. discussion on the spin d. distribution was made. Magnetic susceptibility measurements were performed for three isolated radicals with a SQUID magnetometer. One radical was found to couple ferromagnetically, and anal. with the one-dimensional regular Heisenberg model gave 2J/k_B = 11.2 K. In the experiment, the researchers used many compounds, for example, 2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5SDS of cas: 68385-95-5).

2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).SDS of cas: 68385-95-5

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Biotransformation of 3,5-dibromo-4-hydroxybenzonitrile under denitrifying, Fe(III)-reducing, sulfidogenic, and methanogenic conditions was written by Knight, Victoria K.;Berman, Mitchell H.;Haggblom, Max M.. And the article was included in Environmental Toxicology and Chemistry in 2003.Formula: C7H4BrNO This article mentions the following:

Bromoxynil (3,5-dibromo-4-hydroxybenzonitrile) is a halogenated aromatic nitrile herbicide used on a variety of crops for the postemergence control of annual broad-leaved weeds. The anaerobic biodegradability of bromoxynil and its aerobic transformation product, 3,5-dibromo-4-hydroxybenzoate, were examined in enrichment cultures established with anaerobic sediment under denitrifying, Fe(III)-reducing, sulfidogenic, and methanogenic conditions. Bromoxynil (100μM) was depleted in 20-30 days in the methanogenic, sulfidogenic, and Fe(III)-reducing enrichments but was stable under denitrifying conditions. The 3,5-dibromo-4-hydroxybenzoate (100μM) was depleted within 20-35 days under all 4 anaerobic conditions. Both compounds were stable in sterile controls. Bromoxynil and 3,5-dibromo-4-hydroxybenzoate were readily utilized upon respiking of the cultures. During utilization of bromoxynil, stoichiometric release of bromide was observed with transient accumulation of metabolites identified as bromocyanophenol, cyanophenol, and phenol. Bromoxynil heptanoate and octanoate were rapidly hydrolyzed to bromoxynil, which was further degraded. These results indicate that bromoxynil and 3,5-dibromo-4-hydroxybenzoate are degraded under different anaerobic conditions. Anaerobic degradation of bromoxynil proceeds via reductive debromination to 4-cyanophenol, which is further transformed to phenol and can ultimately be degraded to carbon dioxide. In the experiment, the researchers used many compounds, for example, 2-Bromo-4-hydroxybenzonitrile (cas: 82380-17-4Formula: C7H4BrNO).

2-Bromo-4-hydroxybenzonitrile (cas: 82380-17-4) 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.Formula: C7H4BrNO

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Nitrile – Wikipedia,
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Catalytic enantioselective addition of methyltriisopropoxititanium to aldehydes was written by Veguillas, Marcos;Sola, Ricard;Fernandez-Ibanez, M. Angeles;Macia, Beatriz. And the article was included in Tetrahedron: Asymmetry in 2016.SDS of cas: 101219-69-6 This article mentions the following:

An efficient catalyst for the enantioselective synthesis of chiral Me carbinols from aldehydes is presented. The system uses methyltriisopropoxytitanium as a nucleophile and a readily available binaphthyl derivative as a chiral ligand. The enantioselective methylation of both aromatic and aliphatic aldehydes proceeds with good yields and high enantioselectivities under mild conditions. In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6SDS of cas: 101219-69-6).

(R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. 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.SDS of cas: 101219-69-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts