Tag: 100-200

An NMR investigation of ground-state polarization of some substituted aromatic systems was written by Collins, Michael J.;Hatton, Paul M.;Sternhell, Sever. And the article was included in Australian Journal of Chemistry in 1992.Recommanded Product: 5-Methyl-2-nitrobenzonitrile This article mentions the following:

A previously established NMR method for estimating mobile bond orders was used to examine the ground-state polarization of benzene or heteroaromatic derivatives with ortho or para pairs of +R/-R substituents in benzene, naphthalene, furan, thiophene, pyrrole, quinoline, and pyrazole systems. Evidence for significant ground-state polarization which is solvent-independent was observed in these systems, especially benzene, pyrrole, and pyrazole. In the experiment, the researchers used many compounds, for example, 5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6Recommanded Product: 5-Methyl-2-nitrobenzonitrile).

5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6) 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: 5-Methyl-2-nitrobenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis and biological evaluation of novel dihydro-aryl/alkylsulfanyl-cyclohexylmethyl-oxopyrimidines (S-DACOs) as high active anti-HIV agents was written by He, Yan-Ping;Long, Jin;Zhang, Shui-Shuan;Li, Cong;Lai, Christopher Cong;Zhang, Chun-Sheng;Li, Da-Xiong;Zhang, De-Hua;Wang, Hua;Cai, Qing-Qing;Zheng, Yong-Tang. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2011.Recommanded Product: 2-Cyclohexylacetonitrile This article mentions the following:

A novel dihydro-aryl/alkylsulfanyl-cyclohexylmethyl-oxopyrimidines (S-DACOs), e.g., I, combinatory library was synthesized and evaluated with C8166 cells infected by the HIV-1_IIIB in vitro, using Nevirapine (NVP) and Zidovudine (AZT) as pos. control. The anti-HIV screening results revealed that C-6-cyclohexylmethyl substituted pyrimidinones possessed higher selective index than its 6-arylmethyl counterparts. Some compounds showed potent anti-HIV activities with EC₅₀ values of 0.012 to 0.162 nM. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Recommanded Product: 2-Cyclohexylacetonitrile).

2-Cyclohexylacetonitrile (cas: 4435-14-7) 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. Recommanded Product: 2-Cyclohexylacetonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Tetrahydro-ar-1-(and 2)-naphthoic acids and their derivatives was written by Sergievskaya, S. I.;Nikhamkina, E. G.. And the article was included in Zhurnal Obshchei Khimii in 1945.Name: 5,6,7,8-Tetrahydronaphthalene-1-carbonitrile This article mentions the following:

ar-1-Aminotetralin (45 g.), 75 cc. concentrated HCl, and 200 cc. water were mixed and treated with sufficient water to dissolve the HCl salt; diazotization by 22.5 g. NaNO₂ in 300 cc. water at -5°, followed by addition to 56 g. NaCN in 500 cc. water, 80 cc. 10% NH₄OH, and 33 g. CuCl, stirring for 2-3 hrs., and steam distillation gave 5,6,7,8-tetrahydro-1-naphthonitrile (35.7%), b₅ 130-1°, b₁₇ 156-7°. Heating 15.7 g. of above with 19.8 g. NaOH, 75 cc. EtOH, and 5 cc. water at reflux gave 13 g. of the corresponding acid (I), m. 139-40° (after crystallization, m. 150-1°; solvent not given) and 0.5 g. amide (no m.p.); the hydrolysis may be conducted in a sealed tube at 140° for 8 hrs., using concentrated HCl, although the yield is lowered (ca. 50%); the same acid was obtained after alc. KOH hydrolysis of the hydrogenation product of Et 1-naphthoate. I (5 g.), 17 cc. absolute EtOH, and 1.5 cc. concentrated H₂SO₄, heated 6 hrs., yielded the Et ester, b₄128-9°; hydrogenation of Et 1-naphthoate in EtOH, using Raney Ni at 130° and 50 atm., gave the same ester, b₁₈ 165-70°. Chloride of I, obtained by heating 12 g. I with 100 g. SOCl₂, b₃ 122-3°. Treatment of this with NH₄OH gave the amide, m. 181-2° (from EtOH). The chloride (1.8 g.) in dry benzene and 2 g. Et₂NCH₂CH₂OH were refluxed for 2 hrs., and after the usual treatment, treated with Et₂O-HCl to give 2-diethylaminoethyl 5,6,7,8-tetrahydro-1-naphthoate-HCl, m. 161-2° (from benzene). Similar procedures were used in the preparation of 5,6,7,8-tetrahydro-2-naphthonitrile (from ar-2-aminotetralin), b₄ 103-4° (36%); acid, m. 153° (from EtOH) (96%); Et ester, b₄ 135.5°, b₈ 147°; chloride, b₃ 115-16°; amide, m. 140-1° (from EtOH); 2-diethylaminoethyl ester-HCl, m. 152-3° (from benzene). The alkylamino esters are weak anesthetics. In the experiment, the researchers used many compounds, for example, 5,6,7,8-Tetrahydronaphthalene-1-carbonitrile (cas: 29809-13-0Name: 5,6,7,8-Tetrahydronaphthalene-1-carbonitrile).

5,6,7,8-Tetrahydronaphthalene-1-carbonitrile (cas: 29809-13-0) 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. 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: 5,6,7,8-Tetrahydronaphthalene-1-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Challenging nickel-catalysed amine arylations enabled by tailored ancillary ligand design was written by Lavoie, Christopher M.;MacQueen, Preston M.;Rotta-Loria, Nicolas L.;Sawatzky, Ryan S.;Borzenko, Andrey;Chisholm, Alicia J.;Hargreaves, Breanna K. V.;McDonald, Robert;Ferguson, Michael J.;Stradiotto, Mark. And the article was included in Nature Communications in 2016.HPLC of Formula: 60710-80-7 This article mentions the following:

An operationally simple and air-stable ligand/nickel(II) pre-catalyst that accommodated the broadest combination of C(sp²)-N coupling partners reported to date for any single nickel catalyst, without the need for a precious-metal co-catalyst was reported. Key to the unprecedented performance of this pre-catalyst was the application of the new, sterically demanding yet electron-poor bisphosphine PAd-DalPhos. Featured were the first reports of nickel-catalyzed room temperature reactions involving challenging primary alkylamine and ammonia reaction partners employing an unprecedented scope of electrophiles, including transformations involving sought-after (hetero)aryl mesylates for which no capable catalyst system was known. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methylbenzonitrile (cas: 60710-80-7HPLC of Formula: 60710-80-7).

3-Amino-4-methylbenzonitrile (cas: 60710-80-7) 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. 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.HPLC of Formula: 60710-80-7

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Substrate profiling of the cobalt nitrile hydratase from Rhodococcus rhodochrous ATCC BAA 870 was written by Mashweu, Adelaide R.;Chhiba-Govindjee, Varsha P.;Bode, Moira L.;Brady, Dean. And the article was included in Molecules in 2020.Reference of 1753-48-6 This article mentions the following:

The aromatic substrate profile of the cobalt nitrile hydratase from Rhodococcus rhodochrous ATCC BAA 870 was evaluated against a wide range of nitrile containing compounds (>60). To determine the substrate limits of this enzyme, compounds ranging in size from small (90 Da) to large (325 Da) were evaluated. Larger compounds included those with a bi-aryl axis, prepared by the Suzuki coupling reaction, Morita-Baylis-Hillman adducts, heteroatom-linked diarylpyridines prepared by Buchwald-Hartwig cross-coupling reactions and imidazo[1,2-a]pyridines prepared by the Groebke-Blackburn-Bienayme multicomponent reaction. The enzyme active site was moderately accommodating, accepting almost all of the small aromatic nitriles, the diarylpyridines and most of the bi-aryl compounds and Morita-Baylis-Hillman products but not the Groebke-Blackburn-Bienayme products. Nitrile conversion was influenced by steric hindrance around the cyano group, the presence of electron donating groups (e.g., methoxy) on the aromatic ring, and the overall size of the compound In the experiment, the researchers used many compounds, for example, 2-Aminopyrimidine-5-carbonitrile (cas: 1753-48-6Reference of 1753-48-6).

2-Aminopyrimidine-5-carbonitrile (cas: 1753-48-6) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. 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 1753-48-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The taste of 1-alkoxy- and 1-halo-2-amino-4-cyanobenzenes was written by Blanksma, J. J.;Petri, E. M.. And the article was included in Recueil des Travaux Chimiques des Pays-Bas et de la Belgique in 1947.Recommanded Product: 60979-25-1 This article mentions the following:

The 1-alkoxy- and 1-halo-2-amino-4-cyanobenzenes are less sweet than the corresponding nitrobenzenes, though still much sweeter than cane sugar, the 1-methoxy-(I) being 180, 1-ethoxy-(II) 900, 1-propoxy-(III) 2,500, 1-chloro-(IV) 300, and 1-bromo-2-amino-4-cyanobenzene (V) 500 times as sweet as sucrose. Acylation destroyed the sweet taste. I, m. 84°, was prepared by treating 4,2-NC(O₂N)C₆H₃Cl with MeONa and reducing the product with Na₂S₂; N-Ac, m. 186°, Bz, m. 117°, and carbethoxy derivative, m. 103°, were tasteless as were 1-methoxy-2-nitro-4-carbamylbenzene, m. 117°, and 1-methoxy-2-nitro-4-aminobenzene, m. 49°. Similarly II, m. 112°, its N-Ac, m. 168°, Bz, m. 140°, and carbethoxy derivatives, m. 89°, and 1-ethoxy-2-nitro-4-carbamylbenzene (VI), m. 175°, were prepared VI and NaOCl produced tasteless 1-ethoxy-2-nitro-4-aminobenzene, m. 41°. 1-Propoxy-2-nitro-4-cyanobenzene (VII), m. 105°, was prepared and reduced to III, m. 99° (N-Ac, m. 178°, Bz, m. 135°, and carbethoxy derivatives, m. 66°). The hydrolysis of III to 1-propoxy-2-amino-4-carbamylbenzene (VIII), m. 171°, destroyed the sweetness; Ac derivative of VIII m. 198°; Bz derivative m. 198°. 1-Propoxy-2-nitro-4-carbamylbenzene, m. 158°, is also tasteless. 4-Chlorobenzamide is tasteless but 1-chloro-2-nitro-4-cyanobenzene is 75 times and 1-chloro-2-amino-4-cyanobenzene (IX), m. 92°, 300 times as sweet as sucrose; the Ac derivative of IX, m. 158°, Bz derivative, m. 166°, and 3,5-di-Br derivative, m. 171°, are all tasteless. 1-Chloro-2-nitro-4-carbamylbenzene, m. 156°, 1-chloro-2-amino-4-carbamylbenzene (X), m. 164°, and its 2-AcNH, m. 220°, 2-Ac₂N, m. 200°, 2-BzNH, m. 215°, 2-carbethoxyamino, m. 162°, and 3,5-di-Br derivative, m. 248°, are also tasteless. V, m. 99°, was prepared by reducing 2,4-O₂N(NC)C₆H₃Br; its Ac, m. 185°, Bz, m. 160°, carbethoxy, m. 115°, and 3,5-di-Br derivative, m. 180°. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methoxybenzonitrile (cas: 60979-25-1Recommanded Product: 60979-25-1).

3-Amino-4-methoxybenzonitrile (cas: 60979-25-1) 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. 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. Recommanded Product: 60979-25-1

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

New thiophene-acridine compounds: Synthesis, antileishmanial activity, DNA binding, chemometric, and molecular docking studies was written by Serafim, Vanessa de Lima;Felix, Mayara Barbalho;Silva, Daiana Karla Frade;Rodrigues, Klinger Antonio da Franca;Andrade, Patricia Neris;Vitalino de Almeida, Sinara Monica;de Albuquerque dos Santos, Sanderssonilo;Ferreira de Oliveira, Jamerson;Alves de Lima, Maria do Carmo;Mendonca-Junior, Francisco Jaime Bezerra;Scotti, Marcus Tullius;Rosa de Oliveira, Marcia;Olimpio de Moura, Ricardo. And the article was included in Chemical Biology & Drug Design in 2018.Synthetic Route of C8H8N2S This article mentions the following:

In this study, we synthesized eight new compounds containing the 2-amino-cycloalkyl[b]thiophene and acridine moieties (ACT₀₁ and ACS₀₁-ACS₀₇). None tested compounds presented human erythrocyte cytotoxicity. The new compounds presented antipromastigote activity, where ACS₀₁ and ACS₀₂ derivatives presented significant antileishmanial activity, with better performance than the reference drugs (tri and pentavalent antimonials), with resp. IC₅₀ values of 9.60 ± 3.19 and 10.95 ± 3.96 μm. Addnl., these two derivatives were effective against antimony-resistant Leishmania (Leishmania) amazonensis strains. In addition, binding and fragmentation DNA assays were performed. It was observed that the antileishmanial activity of ACS₀₁ is not associated with DNA fragmentation of the promastigote forms. However, it interacted with DNA with a binding constant of 10⁴ M^-1. In partial least-squares studies, it was observed that the most active compounds (ACS₀₁ and ACS₀₂) showed lower values of amphiphilic moment descriptor, but there was a correlation between the lipophilicity of the mols. and antileishmanial activity. Furthermore, the docking mol. studies showed interactions between thiophene-acridine derivatives and the active site of pyruvate kinase enzyme with the major contribution of asparagine 152 residue for the interaction with thiophene moiety. Thus, the results suggested that the new thiophene-acridine derivatives are promising mols. as potential drug candidates. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Synthetic Route of C8H8N2S).

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. 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. Synthetic Route of C8H8N2S

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Decomposition of thiopyrans to thiophenes under electron impact was written by Bogdanowicz-Szwed, Krystyna;Nagraba, Krzysztof. And the article was included in Organic Mass Spectrometry in 1984.Synthetic Route of C8H8N2S This article mentions the following:

Fragmentation patterns for I (n = 3, 4, 5; R = H, Cl, Br, Me) are discussed. The mass spectra of I showed peaks of high intensity in the mol. ion region, with rel. abundance varying from 20 to 60% of the base peak. The fragmentation of the [I]⁺· occurred as a one-step process with ejection of RC₆H₄NC as well as by a two-step process involving loss of RC₆H₄· and CN· radicals. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Synthetic Route of 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. 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.Synthetic Route of C8H8N2S

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Asymmetric catalytic reduction of carbonyl compounds using C₂ symmetric diamines as chiral ligands was written by Gamez, Patrick;Fache, Fabienne;Lemaire, Marc. And the article was included in Tetrahedron: Asymmetry in 1995.Safety of (R)-4-(1-Hydroxyethyl)benzonitrile This article mentions the following:

The catalytic asym. reduction of prochiral ketones by hydride transfer using various C₂ sym. chiral diamines as ligands and rhodium complexes is studied. Kinetic studies show an increase in the enantiomeric excess with the conversion. In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6Safety of (R)-4-(1-Hydroxyethyl)benzonitrile).

(R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6) 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. 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.Safety of (R)-4-(1-Hydroxyethyl)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Acylpyridines. III. Reaction of 1-methoxy-4-alkoxypyridinium salts with potassium cyanide was written by Nishimoto, Nobushige;Nakashima, Tatsumi. And the article was included in Yakugaku Zasshi in 1962.Safety of 4-methoxypicolinonitrile This article mentions the following:

By the reaction of 1, 4-dimethoxypyridinium iodide with KCN in MeOH, 4-MeOC₅H₄N (1), Me 4-cyanopicolinimidate, Me 4-methoxypicolinimidate, di-Me 3,4-pyridinecarboximidate, 4-methoxypicolinamide, 2,4,6-tris(4-methoxy-2-pyridyl)- 1,3,5-triazine, 4-cyanopicolinamide (II), and 2,4-pyridinecarboxamide (III) were produced but a very little of the expected 4-methoxypicolinonitrile (IV) was obtained. When dioxane was used instead of MeOH, IV was obtained in 30% yield, besides a small amount of I and 2,4-pyridinedicarbonitrile (V). On the other hand, 1-methoxy-4-ethoxypyridinium iodide treated with KCN in MeOH gave 4-ethoxypyridine, 4-ethoxypicolinamide, II, and III. In dioxane, 4-ethoxypicolinonitrile was obtained in 32% yield, together with V and 4-EtOC₅H₄N. In the experiment, the researchers used many compounds, for example, 4-methoxypicolinonitrile (cas: 36057-44-0Safety of 4-methoxypicolinonitrile).

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts