Author: Jessica.F

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

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Heterometallic Coordination Polymers Assembled from Trigonal Trinuclear Fe₂Ni-Pivalate Blocks and Polypyridine Spacers: Topological Diversity, Sorption, and Catalytic Properties was written by Sotnik, Svetlana A.;Polunin, Ruslan A.;Kiskin, Mikhail A.;Kirillov, Alexander M.;Dorofeeva, Victoria N.;Gavrilenko, Konstantin S.;Eremenko, Igor L.;Novotortsev, Vladimir M.;Kolotilov, Sergey V.. And the article was included in Inorganic Chemistry in 2015.Recommanded Product: 55490-87-4 This article mentions the following:

Linkage of the trigonal complex [Fe₂NiO(Piv)₆] (Piv^– = pivalate) by polypyridine ligands, namely, tris(4-pyridyl)triazine (L²), 2,6-bis(3-pyridyl)-4-(4-pyridyl)pyridine (L³), N-(bis-2,2-(4-pyridyloxymethyl)-3-(4-pyridyloxy)propyl)pyridone-4 (L⁴), and 4-(N,N-diethylamino)phenyl-bis-2,6-(4-pyridyl)pyridine (L⁵) gave novel coordination polymers [Fe₂NiO(Piv)₆(L²)]_n (2), [Fe₂NiO(Piv)₆(L³)]_n (3), [Fe₂NiO(Piv)₆(L⁴)]_n·nHPiv (4), and [{Fe₂NiO(Piv)₆}₄{L⁵}₆]_n·3nDEF (5, where DEF is N,N-diethylformamide), which were crystallog. characterized. The topol. anal. of 3, 4, and 5 disclosed the 3,3,4,4-connected 2-dimensional (3, 4) or 3,4,4-connected 1-dimensional (5) underlying networks which, upon further simplification, gave rise to the uninodal 3-connected nets with the resp. fes (3, 4) or SP 1-periodic net (4,4)(0,2) (5) topologies, driven by the cluster [Fe₂Ni(μ₃-O)(μ-Piv)₆] nodes and the polypyridine μ₃-L^3,4 or μ₂-L⁵ blocks. The obtained topologies were compared with those identified in other closely related derivatives [Fe₂NiO(Piv)₆(L¹)]_n (1) and {Fe₂NiO(Piv)₆}₈{L⁶}₁₂ (6), where L¹ and L⁶ are tris(4-pyridyl)pyridine and 4-(N,N-dimethylamino)phenyl-bis-2,6-(4-pyridyl)pyridine, resp. A key structure-driven role in defining the dimensionality and topol. of the resulting coordination network is played by the type of polypyridine spacer. Compounds 2 and 3 possess a porous structure, as confirmed by the N₂ and H₂ sorption data at 78 K. Methanol and ethanol sorption by 2 was also studied indicating that the pores filled by these substrates did not induce any structural rearrangement of this sorbent. Addnl., porous coordination polymer 2 was also applied as a heterogeneous catalyst for the condensation of salicylaldehyde or 9-anthracenecarbaldehyde with malononitrile. The best activity of 2 was observed in the case of salicylaldehyde substrate, resulting in up to 88% conversion into 2-imino-2H-chromen-3-carbonitrile. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Recommanded Product: 55490-87-4).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) 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: 55490-87-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some amine derivatives of acrylonitrile was written by Wiedemann, O. F.;Montgomery, W. H.. And the article was included in Journal of the American Chemical Society in 1945.Recommanded Product: 3,3′,3”-Nitrilotripropanenitrile This article mentions the following:

Correction. In C.A. 40, 832.2 the m.p. of IV is 59°, not 99°. n_D²⁵ of VI is 1.4802, not 1.4910. (CH₂)₂O in line 38 should read HOCH₂CH₂CN. 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 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: 3,3′,3”-Nitrilotripropanenitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Discovery of 4-aminopyrimidine analogs as highly potent dual P70S6K/Akt inhibitors was written by Xiao, Yufang;Huck, Bayard R.;Lan, Ruoxi;DeSelm, Lizbeth;Chen, Xiaoling;Qiu, Hui;Neagu, Constantin;Johnson, Theresa;Mochalkin, Igor;Gardberg, Anna;Jiang, Xuliang;Tian, Hui;Dutt, Vikram;Santos, Dusica;Head, Jared;Jackson, Jennifer;Syed, Sakeena;Lin, Jing;Wilker, Erik;Ma, Jianguo;Clark, Anderson;Machl, Andreas;Bankston, Donald;Jones, Christopher C. V.;Goutopoulos, Andreas;Sherer, Brian. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2021.Safety of 4-Amino-6-chloropyrimidine-5-carbonitrile This article mentions the following:

Activation of the PI3K/Akt/mTOR kinase pathway is associated with human cancers. A dual p70S6K/Akt inhibitor is sufficient to inhibit strong tumor growth and to block neg. impact of the compensatory Akt feedback loop activation. A scaffold docking strategy based on an existing quinazoline carboxamide series identified 6-[4-(2-Amino-1-phenyl-ethyl)-piperazin-1-yl]-5-(4-fluoro-phenyl)-pyrimidin-4-ylamine, which showed a single-digit nanomolar and a micromolar potencies in p70S6K and Akt enzymic assays. SAR optimization improved Akt enzymic and p70S6K cellular potencies, reduced hERG liability, and ultimately discovered the promising candidate 4-Amino-6-{4-[1-(2-azetidin-1-yl-ethyl)-4-(4-fluoro-3-trifluoromethyl-phenyl)-1H-imidazol-2-yl]-piperidin-1-yl}pyrimidine-5-carboxylic acid amide, which exhibited with a single digit nanomolar value in both p70S6K and Akt biochem. assays, and hERG activities (IC50 = 17.4 μM). This agent demonstrated dose-dependent efficacy in inhibiting mice breast cancer tumor growth and covered more than 90% pS6 inhibition up to 24 h at a dose of 200 mg/kg po. In the experiment, the researchers used many compounds, for example, 4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4Safety of 4-Amino-6-chloropyrimidine-5-carbonitrile).

4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4) 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.Safety of 4-Amino-6-chloropyrimidine-5-carbonitrile

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Novel pyrazolo[1,5-a]pyridines as p110α-selective PI3 kinase inhibitors: Exploring the benzenesulfonohydrazide SAR was written by Kendall, Jackie D.;Giddens, Anna C.;Tsang, Kit Yee;Frederick, Raphael;Marshall, Elaine S.;Singh, Ripudaman;Lill, Claire L.;Lee, Woo-Jeong;Kolekar, Sharada;Chao, Mindy;Malik, Alisha;Yu, Shuqiao;Chaussade, Claire;Buchanan, Christina;Rewcastle, Gordon W.;Baguley, Bruce C.;Flanagan, Jack U.;Jamieson, Stephen M. F.;Denny, William A.;Shepherd, Peter R.. And the article was included in Bioorganic & Medicinal Chemistry in 2012.SDS of cas: 60710-80-7 This article mentions the following:

Structure-activity relationship studies of the pyrazolo[1,5-a]pyridine class of PI3 kinase inhibitors show that substitution off the hydrazone nitrogen and replacement of the sulfonyl both gave a loss of p110α selectivity, with the exception of an N-hydroxyethyl analog. Limited substitutions were tolerated around the Ph ring; in particular the 2,5-substitution pattern was important for PI3 kinase activity. The N-hydroxyethyl compound also showed good inhibition of cell proliferation and inhibition of phosphorylation of Akt/PKB, a downstream marker of PI3 kinase activity. It had suitable pharmacokinetics for evaluation in vivo, and showed tumor growth inhibition in two human tumor cell lines in xenograft studies. This work has provided suggestions for the design of more soluble analogs. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methylbenzonitrile (cas: 60710-80-7SDS of cas: 60710-80-7).

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Structurally novel PI3Kδ/γ dual inhibitors characterized by a seven-membered spirocyclic spacer: The SARs investigation and PK evaluation was written by Tao, Qiangqiang;Chen, Yuqing;Liang, Xiao;Hu, Yongzhou;Li, Jiaming;Fang, Fang;Wang, Huchuan;Meng, Chang;Liang, Jingtai;Ma, Xiaodong;Gui, Shuangying. And the article was included in European Journal of Medicinal Chemistry in 2020.HPLC of Formula: 60025-09-4 This article mentions the following:

Herein, we communicate our recent medicinal chem. efforts which have culminated in a series of PI3Kδ/γ dual inhibitors structurally featuring a seven-membered spirocyclic spacer. Compound 26, the most potent one among them, exhibited superior PI3Kδ inhibitory activity (IC₅₀ = 1.0 nM) to that of the approved PI3Kδ inhibitor Idelalisib. Besides, it exerted remarkable anti-proliferative efficacy against human malignant B-cell line SU-DHL-6 with GI₅₀ value of 33 nM. The biochem. assay against the other three class I PI3K isoforms identified compound 26 as a potent PI3Kδ/γ dual inhibitor with considerable selectivity over PI3Kα and PI3Kβ. In SU-DHL-6 cells, a dramatic down-regulation of PI3K signaling was observed following compound 26-treatment at the concentration as low as 10 nM. Inspiringly, the pharmacokinetic (PK) study in Sprague-Dawley (SD) rats revealed it was orally available with a favorable bioavailability (F = 87.5%). Overall, compound 26, a promising PI3Kδ/γ dual inhibitor, has the potential to emerge as a clin. candidate for the treatment of leukocyte-mediated malignancies after extensive functional investigation. In the experiment, the researchers used many compounds, for example, 4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4HPLC of Formula: 60025-09-4).

4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.HPLC of Formula: 60025-09-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Iridium-catalyzed α-alkylation of acetonitrile with primary and secondary alcohols was written by Sawaguchi, Takuya;Obora, Yasushi. And the article was included in Chemistry Letters in 2011.Application In Synthesis of 2-Cyclohexylacetonitrile This article mentions the following:

Acetonitrile is successfully alkylated with primary and secondary alcs. in the presence of t-BuOK using [Ir(OH)(cod)]₂ as a catalyst. This method provides a very clean and atom-economical convenient direct route to substituted nitriles, which are very important raw materials in organic and industrial chem. 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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Anodic cyanation of tert-butylated anisoles: competitive aromatic additions and substitutions was written by Yoshida, Kunihisa;Takeda, Kazusada;Fueno, Takayuki. And the article was included in Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) in 1993.Computed Properties of C11H13N This article mentions the following:

The electrooxidation of several tert-butylated anisoles has been carried out in methanol containing sodium cyanide at a Pt anode in a divided cell. Two types of reactions occurred competitively, aromatic-ring addition and substitution. Increasing the level of tert-Bu substitution raises the relative extent of addition to the aromatic ring. The order of orientational preference for substitution of the aromatic hydrogen of alkylanisole cation radicals is explained in terms of the LUMO electron densities calculated for the cation radicals. The effect of structure on the oxidation potential of alkylanisoles has also been studied. Para substitution lowers the oxidation potential while ortho substitution raises the potential. In the experiment, the researchers used many compounds, for example, 3-(tert-Butyl)benzonitrile (cas: 154532-34-0Computed Properties of C11H13N).

3-(tert-Butyl)benzonitrile (cas: 154532-34-0) 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.Computed Properties of C11H13N

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Cobalt in N-doped carbon matrix catalyst for chemoselective hydrogenation of nitroarenes was written by Dai, Yihu;Jiang, Chunyang;Xu, Min;Bian, Bo;Lu, Di;Yang, Yanhui. And the article was included in Applied Catalysis, A: General in 2019.Recommanded Product: 2-Amino-4-(trifluoromethyl)benzonitrile This article mentions the following:

Anilines as important intermediates for both organic synthesis and industrial manufactory are densely substituted with a variety of functional moieties, and the transformation of nitroarenes into corresponding anilines requires catalytically selective hydrogenation catalyst. Herein, we describe a simple pyrolysis strategy to prepare cobalt catalysts in nitrogen-doped carbon matrix applied in the selective hydrogenation of nitroarenes with mol. hydrogen. The Co/NC catalysts are obtained through thermal treatment of mixed precursors of cobalt phthalocyanine and melamine. The surface-modified Co particles with Co₃O₄ and CoNx sites are surrounded by N-doped carbon layers according to a series of structural characterization results. These Co/NC catalysts are capable of efficiently selective hydrogenation of nitrobenzene and various substituted nitroarenes into corresponding anilines under relatively mild reaction conditions. The optimal catalytic hydrogenation performance is contributed to the fast rate of H₂ dissociated activation on the CoN_x active sites and the facile adsorption of the reactant substances, which is verified by the isotopic H₂-D₂ exchange experiments, reactant adsorption and the ORR reaction tests. Furthermore, the heterogeneous Co/NC catalyst is highly stable without the Co leaching and deactivation issues during the recycling reaction runs. In the experiment, the researchers used many compounds, for example, 2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1Recommanded Product: 2-Amino-4-(trifluoromethyl)benzonitrile).

2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. 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: 2-Amino-4-(trifluoromethyl)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Iron-Catalyzed Tandem Radical Addition/Cyclization: Highly Efficient Access to Methylated Quinoline-2,4-diones was written by Sun, Huan;Jiang, Yue;Lu, Ming-Kun;Li, Yun-Yun;Li, Li;Liu, Ji-Kai. And the article was included in Synlett in 2020.Product Details of 1483-54-1 This article mentions the following:

A visible-light-induced and iron-catalyzed oxidative radical addition/cyclization cascade reaction of N-(o-cyanoaryl)acrylamides I [R¹ = 4-Cl, 5-CF₃, 3-Br, etc.; R² = Me, Bn; R³ = Me, [(2,2-dimethylpropanoyl)oxy]methyl, Bn, Ph, (acetyloxy)methyl, (1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)methyl] with DMSO has been developed. The method exhibits a wide substrate scope and an excellent functional-group tolerance, thus providing an efficient and convenient access to a variety of methylated quinoline-2,4-diones II (R⁴ = 6-Cl, 6-CF₃, 5-Br, etc.). In the experiment, the researchers used many compounds, for example, 2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1Product Details of 1483-54-1).

2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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.Product Details of 1483-54-1

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts