Tag: 100-200

A facile and environmentally benign polyethylene glycol 600-mediated method for the synthesis of densely functionalized 2-aminothiophene derivatives under ultrasonication was written by Akbarzadeh, Ali;Dekamin, Mohammad G.. And the article was included in Green Chemistry Letters and Reviews in 2017.Related Products of 70291-62-2 This article mentions the following:

A green and efficient protocol for the synthesis of densely functionalized 2-aminothiophene derivatives is described by the one-pot three-component Gewald reaction of enolizable carbonyl compounds, malononitrile (or Et cyanoacetate) and elemental sulfur in polyethylene glycol 600, as an eco-friendly reaction medium. The reaction was carried out without using any basic compounds under ultrasonic irradiation and PEG-600 can be recovered and reused at least five times without significant loss of its activity. The merits of this protocol are mild reaction conditions, good yields, short reaction time, simple work-up procedure and recyclability of the reaction medium as well as avoiding the use of any basic catalyst at ambient temperature In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Related Products 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. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Related Products of 70291-62-2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Yeast supported gold nanoparticles: an efficient catalyst for the synthesis of commercially important aryl amines was written by Krishnan, Saravanan;Patel, Paresh N.;Balasubramanian, Kalpattu K.;Chadha, Anju. And the article was included in New Journal of Chemistry in 2021.Application In Synthesis of 2-Amino-4-(trifluoromethyl)benzonitrile This article mentions the following:

Candida parapsilosis ATCC 7330 supported gold nanoparticles (CpGNP), prepared by a simple and green method was selectively reduce nitroarenes and substituted nitroarenes with different functional groups like halides (-F, -Cl, -Br), olefins, esters and nitriles using sodium borohydride. The product aryl amines which were useful for the preparation of pharmaceuticals, polymers and agrochems. were obtained in good yields (up to >95%) using CpGNP catalyst under mild conditions. The catalyst showed high recyclability (�0 cycles) and was a robust free flowing powder, stored and used after eight months without any loss in catalytic activity. In the experiment, the researchers used many compounds, for example, 2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1Application In Synthesis of 2-Amino-4-(trifluoromethyl)benzonitrile).

2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1) belongs to nitriles. Nitrile carbon shifts are in the range of 115�25 ppm whereas in isonitriles the shifts are around 155�65 ppm. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Application In Synthesis of 2-Amino-4-(trifluoromethyl)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Improved method for the synthesis of 4-methylanthranilic acid was written by Takatori, Kichitaro;Asano, Shingo;Usui, Fumio. And the article was included in Gifu Yakka Daigaku Kiyo in 1958.Electric Literature of C8H8N2 This article mentions the following:

An improved synthetic method of synthesis of 4-methylanthranilic acid, effective for the treatment of Yoshida sarcoma, is studied. p-Toluidine (30 g.), 60 cc. alc., and 90 cc. 10% KOH is refluxed 1 hr. to give 97% 3-nitro-p-toluidine (I), orange columns, m. 113-14° (60% alc. or ligroine). I (50 g.) in 135 cc. 50% H₂SO₄ is cooled, treated with 25 g. NaNO₂ and 70 cc. H₂O at -10°, and stirred to give a reddish orange solution containing 3-nitro-p-toluene-diazonium sulfate. This solution is added to warmed (50°) Cu(CN)₂ solution gradually, kept 20 min. more, cooled, and the separated mass extracted with C₆H₆ to give 76% 3-nitro-p-tolunitrile (II), colorless to light yellow needles, m. 96-8° (H₂O). II (20 g.) in 20 g. AcOH is reduced with 90 cc. concentrated HCl and 200 g. leafy Pb at 55-60° to 43%, 3-amino-p-tolunitrile (III), plates, m. 92-4.5° (30% alc.). III (10 g.) and 50 cc. 10% KOH solution is boiled 7 hrs., cooled, neutralized with dilute AcOH, and the precipitate recrystallized from alc. to give 67% 4-methylanthranilic acid (IV), columns, m. 177-8°, violet fluorescence in alc. When this reaction is stopped after boiling only 2 hrs., 2-amino-p-toluamide, plates, m. 144-7°, is obtained. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methylbenzonitrile (cas: 60710-80-7Electric Literature of C8H8N2).

3-Amino-4-methylbenzonitrile (cas: 60710-80-7) 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.Electric Literature of C8H8N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Preparation of N-substituted amidines was written by Cooper, F. C.;Partridge, M. W.. And the article was included in Journal of the Chemical Society in 1953.Application of 5203-15-6 This article mentions the following:

PhNH₂ (I) (10.1 g.), 25.4 g. 4-MeC₆H₄CN (II), 5 g. powd. Na, and 100 cc. PhMe-free C₆H₆ (III) refluxed 3 days and worked up as described by Lottermoser [J. prakt. Chem. 54, 113(1896)] gave 95% 4-MeC₆H₄C(:NH)NHPh (IV) (analyses indicated 88% CN^– and 75% PhMe based on the equation: 2 RCN + ArNH₂ + 2 Na â†?RC(:NAr)NH^– Na⁺ + RH + NaCN). I (20.2 g.), 25.4. g. II, 5 g. powd. Na, and 100 mL. III as in the previous example gave 96% IV and 0.5% kyanphenin (V). I (9.3 g.), 3.9 g. finely powd. NaNH₂ and 100 cc. C₆H₆ refluxed about 1.25 h., 10.3 g. PhCN (VI) added, and the whole refluxed 2.25 h. gave 12.6 g. PhC(:NH)NHPh (VII), m. 114-15°; with granular NaNH₂, the yield of VII was 57%, and with PhNMe₂ as solvent, 23%. I (9.3 g.), 2.3 g. Na, 10.3 g. VI, and 100 cc. dry C₆H₆ refluxed 27 h. evolved no permanent gas; the products were VII, PhCH₂NH₂ (VIII) (identified as benzylammonium picrate), and BzH; I and Na in boiling C₆H₆ gave about 2% PhNHNa; VII and Na in boiling C₆H₆ gave no permanent gas and small amounts of VIII and I; I and VI refluxed 8 h. gave a trace of PhC(:NPh)NHPh. Two procedures were used to prepare the following compounds in procedure A, 0.1 mol each of powd. Na, the amine, and the nitrile in 100 cc. dry C₆H₆ were refluxed 20-30 h., 15 cc. EtOH was added, the base extracted into aqueous MeCH(OH)CO₂H, isolated by addition of aqueous NH₃, and crystallized from petr. ether; in Procedure B, granular NaNH₂ was used in place of the Na of Procedure A (R, R’ in RC(:NH)NHR’, procedure, % yield, m. p., and m.p. of picrate): 4-MeC₆H₄, Ph, A, 65, 151-2°, 152-3°; 4-MeOC₆H₄, Ph, A, 51, 147-8°, 129-30°; 4-ClC₆H₄, Ph, A, 64, 140-1°, 175-6°; 4-sec-BuOC₆H₄, Ph, A, 63, 116.0-16.5°, 138-40°; Ph, 2-MeC₆H₄, A, 61, 109-10°, 152-3°; Ph, 4-MeOC₆H₄, A, 73, 115.5-16.5°, 171-3°; Ph, 2-C₁₀H₇, A, 39 (Procedure B gave 54%), 128.5-9.5°, 216.5-18.0°; Ph, 2-C₅H₄N, A, 65, 98.5-9.5°, 206-7°; Ph, cyclohexyl, A, 43, 115-16°, 142-3°; 2-MeC₆H₄, Ph, B, 47 122-3°, 175-6°; 4-PhOC₆H₄, Ph, A, 83, 183.5-4.5°, 145-6°; Ph, 2-thiazolyl, B, 6, 90-1°, 162-3°; PhCH₂, Ph, B, 64, 140-1°, 109-10°; Me, Ph, B, 36, -, 190-1°; 2-phenylbenzimidazole, B, 72, 299-301°, 275-6° (decomposition). The following were prepared incidental to the above: p-ClC₆H₄NHCPh:NH.HCl.2H₂O, needles, m. 103-6° (decomposition) (from H₂O) {base, m. 114-15° [acetate, needles, m. 131-2° (from C₆H₆); picrate, m. 180-1°]}; N-(2-hydroxyethyl)benzamidinium picrate, prisms, m. 140-2°, solidifies and remelts at 180-215° (decomposition); 4-sec-BuOC₆H₄CN, b_1.3 109-11°, n²⁰_D 1.5256; 4-HOC₆H₄(NHPh):NH.HO₃SPh, m. 180-2°, (picrate, m. 82-4° (from aqueous iso-PrOH), base, small needles, m. 182.5-3.0°). In the experiment, the researchers used many compounds, for example, 4-iso-Butoxybenzonitrile (cas: 5203-15-6Application of 5203-15-6).

4-iso-Butoxybenzonitrile (cas: 5203-15-6) 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. 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.Application of 5203-15-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Nickel-catalyzed cross-coupling of unactivated alkyl halides using bis(pinacolato)diboron as reductant was written by Xu, Hailiang;Zhao, Chenglong;Qian, Qun;Deng, Wei;Gong, Hegui. And the article was included in Chemical Science in 2013.Recommanded Product: 4-methoxypicolinonitrile This article mentions the following:

(Pinacolato)diboron was used as the terminal reductant which allowed the efficient Ni-catalyzed coupling of unactivated secondary and primary alkyl halides, generating the C(sp³)-C(sp³) coupling products in good yields. The mild catalytic conditions displayed an excellent functional group tolerance and good chemoselectivities which required only 1.5 equivalent of primary bromides for the coupling with secondary bromides. Mechanistic studies suggest that an in-situ organoborane/Suzuki process was not likely and was proved that the base and ligand had more profound impact on selecting this reductive coupling pathway. The good chemoselectivity appears to be evoked by the formation of Ni-Bpin catalytic intermediates which demands matched sizes and reactivities of the alkyl halide coupling partners for optimal coupling efficiency. In the experiment, the researchers used many compounds, for example, 4-methoxypicolinonitrile (cas: 36057-44-0Recommanded Product: 4-methoxypicolinonitrile).

4-methoxypicolinonitrile (cas: 36057-44-0) 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. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Recommanded Product: 4-methoxypicolinonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

La-Mg mixed oxide as a highly basic water resistant catalyst for utilization of CO₂ in the synthesis of quinazoline-2,4(1H,3H)-dione was written by Rasal, Kalidas B.;Yadav, Ganapati D.. And the article was included in RSC Advances in 2016.Application In Synthesis of 2-Amino-3-chlorobenzonitrile This article mentions the following:

The synthesis of quinazoline-2,4(1H,3H)-dione was done by direct utilization of CO₂ in the cyclization of 2-aminobenzonitrile (2-ABN) using lanthanum magnesium mixed oxide (La-Mg MO) as a strong basic catalyst under mild reaction conditions in water. It gave a conversion of~92% with 100% selectivity at 140 °C in 14 h. La-Mg MO was prepared by hydrothermal method using urea as homogeneous precipitating agent. The catalyst was characterized by different anal. techniques like BET, XRD, FT-IR, scanning electron microscope, and TGA, and the basicity by CO₂-TPD and acidity by NH₃ TPD. Various reaction parameters were studied to predict the reaction mechanism and kinetics. The reaction follows the Langmuir-Hinshelwood-Hougen-Watson (LHHW) type kinetics model with an apparent activation energy of 23.3 kcal mol^-1. The catalyst was recycled three times with an insignificant change in activity. The overall process is clean and green. In the experiment, the researchers used many compounds, for example, 2-Amino-3-chlorobenzonitrile (cas: 53312-77-9Application In Synthesis of 2-Amino-3-chlorobenzonitrile).

2-Amino-3-chlorobenzonitrile (cas: 53312-77-9) 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.Application In Synthesis of 2-Amino-3-chlorobenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

New ligands for nickel catalysis from diverse pharmaceutical heterocycle libraries was written by Hansen, Eric C.;Pedro, Dylan J.;Wotal, Alexander C.;Gower, Nicholas J.;Nelson, Jade D.;Caron, Stephane;Weix, Daniel J.. And the article was included in Nature Chemistry in 2016.Computed Properties of C7H6N2O This article mentions the following:

Ligands are essential for controlling the reactivity and selectivity of reactions catalyzed by transition metals. Access to large phosphine ligand libraries has become an essential tool for the application of metal-catalyzed reactions industrially, but these existing libraries are not well suited to new catalytic methods based on non-precious metals (for example, Ni, Cu and Fe). The development of the requisite nitrogen- and oxygen-based ligand libraries lags far behind that of the phosphines and the development of new libraries is anticipated to be time consuming. Here we show that this process can be dramatically accelerated by mining for new ligands in a typical pharmaceutical compound library that is rich in heterocycles. Using this approach, we were able to screen a structurally diverse set of compounds with minimal synthetic effort and identify several new ligand classes for nickel-catalyzed cross-electrophile coupling. These new ligands gave improved yields for challenging cross-couplings of pharmaceutically relevant substrates compared with those of those of previously published ligands. In the experiment, the researchers used many compounds, for example, 4-methoxypicolinonitrile (cas: 36057-44-0Computed Properties of C7H6N2O).

4-methoxypicolinonitrile (cas: 36057-44-0) belongs to nitriles. Nitrile carbon shifts are in the range of 115�25 ppm whereas in isonitriles the shifts are around 155�65 ppm. 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.Computed Properties of C7H6N2O

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

2-Amino-thiophene derivatives present antileishmanial activity mediated by apoptosis and immunomodulation in vitro was written by Rodrigues, Klinger Antonio da Franca;Dias, Cinthia Nobrega de Sousa;Neris, Patricia Lima do Nascimento;Rocha, Juliana da Camara;Scotti, Marcus Tullius;Scotti, Luciana;Mascarenhas, Sandra Rodrigues;Veras, Robson Cavalcante;Almeida de Medeiros, Isac;Keesen, Tatjana de Souza Lima;Bento de Oliveira, Tiago;Alves de Lima, Maria do Carmo;Balliano, Tatiane Luciano;Mendonca de Aquino, Thiago;Olimpio de Moura, Ricardo;Junior, Francisco Jaime Bezerra Mendonca;de Oliveira, Marcia Rosa. And the article was included in European Journal of Medicinal Chemistry in 2015.Recommanded Product: 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile This article mentions the following:

This study evaluated the effects of 2-amino-thiophene derivatives on the promastigote and amastigote forms of Leishmania amazonensis and their possible mechanisms of action. Initially, the authors evaluated the antileishmanial activity of ten 2-amino-thiophene derivatives on promastigote and axenic amastigote forms of Leishmania amazonensis and their cytotoxicity against murine macrophages and human red blood cells. Three promising compounds were selected for studies of the cell death process using flow cytometry anal. and a DNA fragmentation assay. The effects of the compounds were assessed on intramacrophagic amastigotes, and the modulation of cytokine and NO production was investigated. All thiophene derivatives showed antileishmanial activity against promastigotes and axenic amastigotes with less toxicity for murine macrophages and human red blood cells. The best values were obtained for compounds containing a lateral indole ring. Docking studies suggested that these compounds played an important role in inhibiting trypanothione reductase (TryR) activity. The selected compounds SB-200, SB-44, and SB-83 induced apoptosis in promastigotes involving phosphatidylserine externalization and DNA fragmentation in a pattern similar to that observed for the pos. control. Addnl., SB-200, SB-44, and SB-83 significantly reduced the infection index of macrophages by the parasites; for compounds SB-200 and SB-83 this reduction was associated with increased TNF-α, IL-12, and NO levels. This study demonstrated the effective and selective action of 2-amino-thiophene derivatives against L. amazonensis, resulting in apoptosis-like cell death and immunomodulation in vitro. The results suggest that they are promising compounds for the development of new leishmanicidal drugs. 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. 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: 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Photolysis of 1-aryl-3,3-dialkyltriazenes was written by Lippert, Th.;Stebani, J.;Nuyken, O.;Stasko, A.;Wokaun, A.. And the article was included in Journal of Photochemistry and Photobiology, A: Chemistry in 1994.Reference of 4714-63-0 This article mentions the following:

The photolytic decomposition of substituted 1-phenyl-3,3-diethyl-triazenes has been studied using both pulsed XeCl^* excimer excitation at 308 nm, and continuous-wave irradiation with a xenon lamp. Electron-withdrawing substituents in the para position at the Ph ring are found to decrease both the quantum yield of photolysis and the apparent first-order rate constant of decomposition The reaction proceeds according to an overall one-step pathway; anal. of the photolysis products by gas chromatog.-mass spectrometry is consistent with a radical decomposition mechanism. For the compound 1-(4-nitrophenyl)-3,3-diethyl-triazene, an autocatalytic acceleration of the photolysis was observed during the continuous-wave irradiation, using a xenon lamp source. This phenomenon is analyzed in terms of an involvement of the nitro group: photoreduction of the latter functionality involves the creation of solvent radicals in comparatively large concentrations, which are detected by in-situ ESR experiments These radicals may attack and decompose further mols. of the starting material. In the experiment, the researchers used many compounds, for example, 4-(Ethylamino)benzonitrile (cas: 4714-63-0Reference of 4714-63-0).

4-(Ethylamino)benzonitrile (cas: 4714-63-0) 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. 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 4714-63-0

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Antihypertensive activity of 6-arylpyrido[2,3-d]pyrimidin-7-amine derivatives was written by Bennett, Lawrence R.;Blankley, C. John;Fleming, Robert W.;Smith, Ronald D.;Tessman, Deirdre K.. And the article was included in Journal of Medicinal Chemistry in 1981.Category: nitriles-buliding-blocks This article mentions the following:

Fifty-one title compounds I (R = H, Me, Et, etc.; R¹ = H, Me, OEt, etc.; R² = substituted phenyl) were synthesized and evaluated for antihypertensive activity in the conscious spontaneously hypertensive rat. A number of these compounds, notably 6-(2,6-dichlorophenyl)-2-methylpyrido[2,3-d]pyrimidin-7-amine [76574-80-6], lowered blood pressure in these rats in a gradual and sustained manner to normotensive levels at oral doses of 10-50 mg/kg. Normalized blood pressure levels could then be maintained by single daily oral doses. The effect of structural variation in the 6-aryl group and in the 2 and 4 positions of the pyridopyrimidine ring on activity is reported and discussed. In the experiment, the researchers used many compounds, for example, 2-(2,3-Dichlorophenyl)acetonitrile (cas: 3218-45-9Category: nitriles-buliding-blocks).

2-(2,3-Dichlorophenyl)acetonitrile (cas: 3218-45-9) belongs to nitriles. Nitrile carbon shifts are in the range of 115�25 ppm whereas in isonitriles the shifts are around 155�65 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. Category: nitriles-buliding-blocks

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts