Tag: 100-200

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

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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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

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Nitrile – Wikipedia,
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Facile synthesis of polynuclear heterocycles and acyclic C-nucleosides via α-substituted cinamonitrile (II) was written by Abu-zied, Kh. M.;Hussein, H. A. R.;Abu-Hashem, A. A.. And the article was included in Organic Chemistry: An Indian Journal in 2012.Recommanded Product: 70291-62-2 This article mentions the following:

The synthesis of the target compounds was achieved using 2-amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile as a key starting material. This compound was converted to 4-hydrazinyl-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-d]pyrimidine and a related thione derivative While a 2-hydrazine derivative was obtained upon methylation of the above-mentioned intermediate and reaction of the Me thioether with hydrazine hydrate (99% yield). S-glycosides are produced when a 2,4-dithione derivative reacted with α-D-glucopyranosyl bromide tetraacetate or α-D-galactopyranosyl bromide tetraacetate. Acyclic C-nucleosides were obtained by a reaction of hydrazine derivatives with aldose sugars, aldohexoses (hexoses) or aldopentoses (pentoses) such as D-glucose, D-galactose and D-xylose. The title compounds included derivatives of 9,10-dihydro-8H-cyclopenta[4,5]thieno[3,2-e]-1,2,4-triazolo[4,3-c]pyrimidine (I) and cyclopenta[4,5]thieno[2,3-d]-1,2,4-triazolo[4,3-a]pyrimidine (II). 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. 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.Recommanded Product: 70291-62-2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reagents for new heteroannelation reactions. Part I. Isocyanate-dithioketal reagents was written by Sauter, F.;Froehlich, J.;Shaifullah Chowdhury, A. Z. M.. And the article was included in Scientia Pharmaceutica in 1996.HPLC of Formula: 70291-62-2 This article mentions the following:

(MeS)₂C:NCH₂CO₂Et was reacted with various educts. While heteroaromatic 2-amino esters gave cyclization to a pyrimido moiety, the corresponding 2-amino nitriles led in 1-pot reactions to double-annelation, yielding products with an imidazopyrimido moiety. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2HPLC of Formula: 70291-62-2).

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Contribution to Our Knowledge of the Terpenes and the Ethereal Oils. Eighty-fourth Paper. Carboxylic Acids of Cyclic Hydrocarbons and Their Transformation Products was written by Wallach, O.. And the article was included in Justus Liebigs Annalen der Chemie in 1907.Name: 2-Cyclohexylacetonitrile This article mentions the following:

Acids and bases containing the characteristic groups in the side chain were studied. 1. Cyclohexanone derivatives. Two isomeric acids, (I) and (II) were formed on dehydrating cyclohexanolacetic acid. Δ^2.7-Cyclohexeneacetic acid (II), m. 91°, was prepared as already described (Ibid., 347, 329) added HBr to form a compound, m. 89-90°, C₈H₁₃BrO₂, and Br₂ to form C₄H₁₂Br₂O₂ m. 133-34°. Oxidized with permanganate, cyclohexanone was formed. The isomeric acid, m. 38°, probably structure I, yielded the same compound as the Δ^1.7-acid and the hexanolacetic acid with halogen hydrides. Monochlorcyclohexylacetic acid, m. 83°. Monobromcyclohexylacetic acid, m. 89-90°. Monoiodocyclohexylacetic acid, m. 99-100°. The acid, m. 38°, added two atoms bromine to form a compound, m. 119-20°, and distilled with sulphuric acid yielded a lactone. The acid chloride and the amide, m. 152-53°, were prepared. On oxidation, no definite products could be identified. Cyclohexylacetic acid, b. 245-47°, m. 30-31°, was prepared by reduction (Zn dust and acetic acid) of the brom- or iodo- acid. Amide, m. 168°. Nitrile, b. 215-17°, on reduction yielded, β-cyclohexylethylamine, b. 188-189°. Hydrochloride, m. 252-53°; chlorplatinate, m. 253-54°; ureide, m. 85-86°; methylammonium iodide, m. 221-22°. Cyclohexylmethylamine, b. 162-164°, was prepared from the amide, bromine and alkali. Hydrochloride, m. above 210°. Chlorplatinate, m. 240° (decompose). Ureide, m. 170-72°. Cyclohexylacetic acid distilled with lime yielded the completely hydrated dibenzylketone. Semicarbazone, m. 142-45°. Similarly cyclohexylacetone, b. 198-200°, was prepared. Semicarbazone, m. 165-66°. II Suberone derivatives. The methods used were the same as before. Suberylacetic acid, (cycloheptylacetic acid), b₁₀ 165°. Silver salt. Amide, m. 146-48°. Amine, b. 193-95°, [n]_D=1.4719, hydrochloride, m. 229-32°; chlorplatinate; ureide, m. 127-29°; trimethylammonium iodide, m. 223°. III Cyclopentanone derivatives. Cyclopentylacetic acid, b. 226-30°. Amide, m. 143-45°. Amine, b. 139-45°; hydrocldoride, chlorplatinate. Cyctopentanone and ethyl α-isobrombutyrate condensed with zinc formed pentanolisobutyric ester, b₁₁ 108-13°, which lost water on heating with potassium acid sulphate and yielded cyclopenteneisobutyric acid, b₁₁ 148-50°. Silver salt. HCl was added readily to form monochlorcyclopentylisobutyric acid, m. 122.5-123.5°. Monobromcyclopentylisobutyric acid, m. 113-14°. Moniodocyclopentylisobutyric acid, m. 107-108°. The dry distillation of the pentene isobutyric acid yielded a hydrocarbon, C₁₄H₈, b. 136-37° probably chiefly, since on oxidation cyclopentanone (semicarbazone) was formed. An isomer, was also formed and could also be obtained from the first on prolonged heating with alcoholic sulphuric acid. IV 1,4-Methylcyclohexonone derivatives. (Edgar Evans). 1,4-Methylhexeneacetic acid, (Ibid., 343, 345) CH₃C_6?H₉:CH.CO₂H, m. 42-43°. Monochlorcyclomethylhexylacetic acid, m. 88-89°. Monobromcyclomethylhexylacetic acid, m. 85-86°. Dibromcyclomethylhexylacetic acid, m. 97-99°. Cyclomethylhexeneacetomide, m. 155-56°. Nitrile, b₁₅ 107°, 1,4-Cyclomethylhexylacetic acid, m. 63-65°. Amide, m. 161-62°. V Menthone derivatives (Eduard Schellack). Menthone condensed with methylbromacetate and zinc yielded mentholacetic acid methyl ester, , m. 32-33°, b_.10 136-137°. Acid, m. 82-83°, b₁₁ 193-197°. Brommenthylacetic acid. In the preparation of mentheneacetic acid, a lactone, C₁₂H₂₀O₂, b. 300-305°, [n]_D=1.4781 at 22°, was obtained, which, on boiling with HI and phosphorus yielded a substance, m. 88.5-89.5°, isomeric with the lactone. The liquid lactone was levorotatory, the solid, dextrorotatory. Brommenthylacetic acid reduced gave menthylacetic acid, b₁₁ 166-170°. Amide, m. 148-150°. 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. 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.Name: 2-Cyclohexylacetonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Bovine serum albumin-catalyzed one-pot synthesis of 2-aminothiophenes via Gewald reaction was written by Zhao, Dan-Dan;Li, Li;Xu, Fan;Wu, Qi;Lin, Xian-Fu. And the article was included in Journal of Molecular Catalysis B: Enzymatic in 2013.Quality Control of 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile This article mentions the following:

A novel bovine serum albumin (BSA)-catalyzed Gewald reaction in one-pot was developed in this work. The influence of reaction conditions including solvent, temperature and catalyst loading was investigated, and 12 multi-substituted 2-aminothiophene derivatives were prepared with moderate to excellent yields. Recycle experiments were designed to demonstrate the reusability of BSA. This novel activity of BSA to catalyze Gewald reaction is of practical significance in expanding the application of biocatalysts. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Quality Control of 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. 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. 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.Quality Control of 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Polynitrile- and polyamine-functionalized poly(trimethylenimine) dendrimers was written by Woerner, Christof;Muelhaupt, Rolf. And the article was included in Angewandte Chemie in 1993.Recommanded Product: 3,3′,3”-Nitrilotripropanenitrile This article mentions the following:

Sequential acrylonitrile-condensation and Raney nickel-catalyzed hydrogenation of poly(trimethylenimine) N[CH₂CH₂CH₂N(CH₂CH₂NH₂)₂]₃ gave poly(trimethylenimine) I (X = CN). This sequence was repeated two more times to give a dendrimer complex, which was analyzed spectroscopically. In the experiment, the researchers used many compounds, for example, 3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1Recommanded Product: 3,3′,3”-Nitrilotripropanenitrile).

3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1) 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. 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.Recommanded Product: 3,3′,3”-Nitrilotripropanenitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts