Month: January 2023

Syntheses of cyanothiophenes from halothiophenes was written by Nishimura, Shoji;Imoto, Eiji. And the article was included in Nippon Kagaku Zasshi in 1961.Synthetic Route of C5H2N2O2S This article mentions the following:

2-Iodothiophene (42 g.), 20 g. Cu₂(CN)₂, and 120 cc. pyridine were refluxed 3 hrs., 5060 cc. pyridine distilled, 150 cc. C₆H₆ added, and the mixture refluxed 30 min., cooled, and filtered to give 14.3 g. 2-cyanothiophene (I), b₂₁ 88-90°. A mixture of 2-bromothiophene (32.6 g.), 20 g. Cu₂(CN)₂, and 150 cc. quinoline was refluxed 4 hrs., distilled, and treated with HCl to give 11.3 g.I. Similarly, 3-bromothiophene gave 70% 3-cyanothiophene. Similarly, the following cyanothiophenes were obtained (substituent on the starting material, reaction period in hrs., and % yield given): 2,5-BrNO₂, 4.0, 32; 2,5INO₂, 3.0, 70; 2,3-BrNO₂, 4.0, 35; 3,2-BrNO₂, 4.0, 54; 3,4-Br-NO₂, 4.5, 24; 2,4-BrNO₂, 4.5, 20; 2,5-AcI, 4.5, 44; 2,5-AcBr, 7.0, 20; 2,5-AcCl, 7.0, 0; 2,5-BrCO₂Me, 7.0, 0. The results indicate that reactivity of halogens is I > Br > Cl and the activating ability of substituents is NO₂ Ac > CO₂Me. Reactions of 5- acetyl- 2- bromo- 3- nitrothiophene, 2- bromo- 5- methoxycarbonyl-3-nitrothiophene, 2-bromo- 5- carboxy- 3- nitrothiophene, and 2,5-dibromo-3-nitrothiophene yielded 17% 2-acetyl-4-nitrothiophene, 10% 2-methoxycarbonyl-4-nitrothiophene, 15% 2cyano-3-nitrothiophene (II), and 35% II, resp. Hydrolysis of cyano compounds was carried out by heating with concentrated HCl for 2-3 hrs. but II, 3-cyano-2-nitrothiophene, and 3-cyano-4-nitrothiophene were recovered unchanged. In the experiment, the researchers used many compounds, for example, 4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6Synthetic Route of C5H2N2O2S).

4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. 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.Synthetic Route of C5H2N2O2S

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Optimization of N-benzyl-5-nitrofuran-2-carboxamide as an antitubercular agent was written by Gallardo-Macias, Ricardo;Kumar, Pradeep;Jaskowski, Mark;Richmann, Todd;Shrestha, Riju;Russo, Riccardo;Singleton, Eric;Zimmerman, Matthew D.;Ho, Hsin Pin;Dartois, Veronique;Connell, Nancy;Alland, David;Freundlich, Joel S.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2019.Recommanded Product: 37812-51-4 This article mentions the following:

The optimization campaign for a nitrofuran antitubercular hit (N-benzyl-5-nitrofuran-2-carboxamide; JSF-3449) led to the design, synthesis, and biol. profiling of a family of analogs. These compounds exhibited potent in vitro antitubercular activity (MIC = 0.019-0.20 μM) against the Mycobacterium tuberculosis H37Rv strain and low in vitro cytotoxicity (CC₅₀ = 40- > 120 μM) towards Vero cells. Significant improvements in mouse liver microsomal stability and mouse pharmacokinetic profile were realized by introduction of an α,α-dimethylbenzyl moiety. Among these compounds, JSF-4088 (I) is highlighted due to its in vitro antitubercular potency (MIC = 0.019 μM) and Vero cell cytotoxicity (CC₅₀ > 120 μM). The findings suggest a rationale for the continued evolution of this promising series of antitubercular small mols. In the experiment, the researchers used many compounds, for example, 4-(Morpholinomethyl)benzonitrile (cas: 37812-51-4Recommanded Product: 37812-51-4).

4-(Morpholinomethyl)benzonitrile (cas: 37812-51-4) 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. 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.Recommanded Product: 37812-51-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Iron-Catalyzed Oxidative Amination of Benzylic C(sp³)-H Bonds with Anilines was written by Song, Yan-Ling;Li, Bei;Xie, Zhen-Biao;Wang, Dan;Sun, Hong-Mei. And the article was included in Journal of Organic Chemistry in 2021.Safety of 4-(Benzylamino)benzonitrile This article mentions the following:

Iron-catalyzed oxidative amination of benzylic C(sp³)-H bonds with anilines bearing electron-withdrawing groups (EWGs) or electron-donating groups (EDGs) has been realized based on simple variations of N-substituents on imidazolium cations in novel ionic Fe(III) complexes. The structural modification of the imidazolium cation resulted in regulation of the redox potential and the catalytic performance of the iron metal center. Using DTBP as oxidant, [HItBu][FeBr₄] (1,3-di-tert-butylimidazolium iron tetrabromide) showed the highest catalytic activity for anilines bearing EWGs, while [HIPym][FeBr₄] (1,3-bis(pyrimidin-2-yl)imidazolium iron tetrabromide) was more efficient for EDG-substituted anilines. This work provides an alternative access to benzylamines, e.g., RN(R¹)CH₂Ph [R = 4-O₂NC₆H₄, 2-pyrimidinyl, 8-isoquinolinyl, etc., R¹ = H, Me,], with advantages of both a wide substrate scope and iron catalysis. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Safety of 4-(Benzylamino)benzonitrile).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Safety of 4-(Benzylamino)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Heterocyclic Meisenheimer complexes: kinetic and equilibrium data for methoxide ion attack on various disubstituted 2,4-Y,Z-thiophenes and -selenophenes in methanol was written by Terrier, Francois;Chatrousse, Alain-Pierre;Paulmier, Claude. And the article was included in Journal of Organic Chemistry in 1979.Category: nitriles-buliding-blocks This article mentions the following:

The stabilities of I (R, R¹ = NO₂, NO₂; CN, NO₂; NO₂, CN; X = Se, S) decreased in the stated order of R, R¹ and of X, but different trends were found in kinetic studies. II (R = CN; R¹ = NO₂; X = Se, S) reacted differently with MeO^– than the other II. An ortho-like NO₂ group may affect nucleophilic substitution more than a para-like NO₂ group. In the experiment, the researchers used many compounds, for example, 4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6Category: nitriles-buliding-blocks).

4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. 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.Category: nitriles-buliding-blocks

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

CNDO/2 calculations of molecules. 3. Ionization potential and charge distribution was written by Koppel, I.;Molder, U.. And the article was included in Organic Reactivity (Tartu) in 1981.Recommanded Product: 7528-78-1 This article mentions the following:

For several classes of aliphatic compounds, (e.g., ether, amines), a linear relation is established between ionization energy of the electron localized on a certain atom and semiempirical CNDO/2 charges on the latter. The charge distribution was calculated according to the Mulliken procedure. The correction for the intramol. Madelung potential was introduced into the valence shell ionization potentials. A method for the determination of the ionization potential of the lone pair from photoelectron spectra was suggested. The linearity between CNDO/2 and ab initio (STO-3G and 4-31G basis sets) charge densities was found. In the experiment, the researchers used many compounds, for example, 3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1Recommanded Product: 7528-78-1).

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. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Recommanded Product: 7528-78-1

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Modular Continuous Flow Synthesis of Imatinib and Analogues was written by Fu, Wai Chung;Jamison, Timothy F.. And the article was included in Organic Letters in 2019.Electric Literature of C12H14N2O This article mentions the following:

A modular continuous flow synthesis of imatinib (I) and analogs is reported. Structurally diverse imatinib analogs are rapidly generated using three readily available building blocks via a flow hydration/chemoselective C-N coupling sequence. The newly developed continuous flow hydration and amidation modules each exhibit a broad scope with good to excellent yields. Overall, the method described does not require solvent switches, in-line purifications, or packed-bed apparatuses due to the judicious manipulation of flow setups and solvent mixtures In the experiment, the researchers used many compounds, for example, 4-(Morpholinomethyl)benzonitrile (cas: 37812-51-4Electric Literature of C12H14N2O).

4-(Morpholinomethyl)benzonitrile (cas: 37812-51-4) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 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. Electric Literature of C12H14N2O

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis of cis- and trans-4-cyanocyclohexanol was written by Praefcke, Klaus;Schmidt, Dietmar. And the article was included in Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie in 1980.Application of 24056-34-6 This article mentions the following:

The title 4-cyanocyclohexanols, whose stereochem. was determined by NMR spectroscopy, were prepared for the first time by the reaction of 4-hydroxycyclohexanone with Me₃COK and p-MeC₆H₄SO₃CH₂NC to give a cis-trans mixture of the title compounds, which was separated via column chromatog. of their benzoates followed by hydrolysis. In the experiment, the researchers used many compounds, for example, 4-Hydroxycyclohexanecarbonitrile (cas: 24056-34-6Application of 24056-34-6).

4-Hydroxycyclohexanecarbonitrile (cas: 24056-34-6) 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. 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 24056-34-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Commercial Zinc Oxide: A Facile, Efficient, and Eco-friendly Catalyst for the One-Pot Three-Component Synthesis of Multisubstituted 2-Aminothiophenes via the Gewald Reaction was written by Tayebee, Reza;Ahmadi, S. Javad;Rezaei Seresht, Esmaeil;Javadi, Farzad;Yasemi, Mohammad A.;Hosseinpour, Mohsen;Maleki, Behrouz. And the article was included in Industrial & Engineering Chemistry Research in 2012.Electric Literature of C8H8N2S This article mentions the following:

An eco-friendly, simple, and effective protocol is developed for the synthesis of various multisubstituted 2-aminothiophenes. In the presence of a catalytic amount of ZnO (5 mol %), ketones or aldehydes, malononitrile and elemental sulfur were converted to the corresponding 2-aminothiophene derivatives in moderate to high yields (27%-70%) under solvent-free conditions at 100 °C. Zinc oxide as an efficient, readily available, and reusable catalyst, showed very good catalytic activity for the synthesis of 2-aminothiophene derivatives Thus far, little research has been reported on the Gewald reaction under solvent-free conditions; to the best of our knowledge, this is the first time that it has been proposed as an inexpensive and readily available catalyst for use in the target synthetic route. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Electric Literature of C8H8N2S).

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. 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 C8H8N2S

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Effect of antiprotozoal molecules on hypnospores of Perkinsus spp. parasite was written by Duarte, Samia Sousa;de Moura, Ricardo Olimpio;da Silva, Patricia Mirella. And the article was included in Experimental Parasitology in 2018.Quality Control of 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile This article mentions the following:

Perkinsus protozoan parasites have been associated with high mortality of bivalves worldwide, including Brazil. The use of antiproliferative drugs to treat the Perkinsosis is an unusual prophylactic strategy. However, because of their environment impact it could be used to control parasite proliferation in closed system, such as hatchery. This study evaluated the anti-Perkinsus activity potential of synthesized and com. compounds Viability of hypnospores of Perkinsus spp. was assessed in vitro. Cells were incubated with three 2-amino-thiophene (6AMD, 6CN, 5CN) and one acylhydrazone derivatives (AMZ-DCL), at the concentrations of 31.25; 62.5; 125; 250 and 500μM and one com. chlorinated phenoxy phenol derivative, triclosan (2, 5, 10 and 20μM), for 24-48 h. Two synthetic mols. (6CN and AMZ-DCL) caused a significant decline (38 and 39%, resp.) in hypnospores viability, at the highest concentration (500μM), after 48 h. Triclosan was the most cytotoxic compound, causing 100% of mortality at 20μM after 24 h and at 10μM after 48 h. Cytotoxic effects of the compounds 6CN, AMZ-DCL, and triclosan were investigated by measuring parasite’s zoosporulation, morphol. changes and metabolic activities (esterase activity, production of reactive oxygen species and lipid content). Results showed that zoosporulation occurred in few cell. Triclosan caused changes in the morphol. of hypnospores. The 6CN and AMZ-DCL did not alter the metabolic activities studied while Triclosan significantly increased the production of reactive oxygen species and changed the amount and distribution of lipids in the hypnospores. These results suggest that three compounds had potential to be used as antiprotozoal drugs, although further investigation of their mechanism of action must be enlightened. 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. 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.Quality Control of 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Ring opening of 2-substituted 4-nitrothiophenes with pyrrolidine. Access to new functionalized nitro-unsaturated building blocks was written by Dell’Erba, C.;Gabellini, A.;Novi, M.;Petrillo, G.;Tavani, C.;Cosimelli, B.;Spinelli, D.. And the article was included in Tetrahedron in 2001.Application of 42137-24-6 This article mentions the following:

The reaction conditions of the ring-opening processes of 3-nitrothiophene and of 3-nitrobenzo[b]thiophene with pyrrolidine and AgNO₃ were optimized as well as those of the subsequent S-methylation of the ensuing Ag enethiolates to 4-methylthio-2-nitro-1-pyrrolidino-1,3-butadiene (I) and 1-(2-methylthiophenyl)-1-nitro-2-pyrrolidinoethylene (II). Under such conditions 2-substituted 4-nitrothiophenes consistently gave good yields of the corresponding 4-methylthio-2-nitro-1-pyrrolidino-4-R-1,3-butadienes (pyr-MNRB, R = PhS, PhSO₂, MeS, MeSO₂, MeCO, MeCO₂, and CN). The nitroenamine derivatives I, II, and pyr-MNRB were then reacted with p-MeC₆H₄MgBr to furnish moderate to good yields of 4-methylthio-2-nitro-1-(p-tolyl)-4-R-1,3-butadienes (p-tolyl-MNRB) and 1-(2-methylthiophenyl)-1-nitro-2-(p-tolyl)ethylene(III). Stereochem. of the interesting building blocks I–III, pyr-MNRB, and p-tolyl-MNRB was assigned on the grounds of ¹H NMR data and NOE experiments In the experiment, the researchers used many compounds, for example, 4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6Application of 42137-24-6).

4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. 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. Application of 42137-24-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts