Category: nitriles-buliding-blocks

Copper-Catalyzed Enantioselective Hydrosilylation of Ketones by Using Monodentate Binaphthophosphepine Ligands was written by Junge, Kathrin;Wendt, Bianca;Addis, Daniele;Zhou, Shaolin;Das, Shoubhik;Beller, Matthias. And the article was included in Chemistry – A European Journal in 2010.Formula: C9H9NO This article mentions the following:

The first copper-catalyzed asym. hydrosilylation of carbonyl compounds by using chiral monodentate ligands is presented. Under comparably mild conditions, high yields and enantioselectivities (up to 96% ee) are achieved for a broad range of carbonyl compounds such as aryl alkyl, cyclic, heterocyclic and aliphatic ketones. Compared to other known asym. hydrosilylation catalysts, advantageously no base or fluoride activation is necessary. In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6Formula: C9H9NO).

(R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6) 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. 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.Formula: C9H9NO

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Nitration of moderately deactivated arenes with nitrogen dioxide and molecular oxygen under neutral conditions. Zeolite-induced enhancement of regioselectivity and reversal of isomer ratios was written by Peng, Xinhua;Fukui, Naoyuki;Mizuta, Masayuki;Suzuki, Hitomi. And the article was included in Organic & Biomolecular Chemistry in 2003.SDS of cas: 64113-86-6 This article mentions the following:

In the presence of zeolites, moderately deactivated arenes such as 1-nitronaphthalene, naphthonitriles, and methylated benzonitriles can be smoothly nitrated at room temperature by the combined action of nitrogen dioxide and mol. oxygen. The regioselectivity is considerably improved as compared with the conventional nitration methodol. based on nitric and sulfuric acids. In some cases, the minor isomer became favored to a significant extent, resulting in the reversal of ordinary isomer ratios of nitration products. In the experiment, the researchers used many compounds, for example, 5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6SDS of cas: 64113-86-6).

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

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Nitrile – Wikipedia,
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Immobilized Iron Metal-Containing Ionic Liquid-Catalyzed Chemoselective Transfer Hydrogenation of Nitroarenes into Anilines was written by Patil, Nilesh M.;Sasaki, Takehiko;Bhanage, Bhalchandra M.. And the article was included in ACS Sustainable Chemistry & Engineering in 2016.Computed Properties of C8H8N2 This article mentions the following:

The chemoselective transfer hydrogenation of nitroarenes into anilines was investigated using immobilized iron metal containing ionic liquid (ImmFe-IL) as a versatile heterogeneous catalyst. The present protocol has high atom efficiency with excellent chemoselectivity and regioselectivity. Selective reduction of the nitro group was observed in the presence of other reducing functional groups such as nitrile, ketone, acid, amide, ester, halogens, hydroxyl, olefin, and heterocycles. The developed protocol is also highly selective toward conversion of dinitroarenes into nitroanilines. The present catalytic system uses environmentally benign ethylene glycol as a solvent which is inexpensive, easily available, nontoxic, nonvolatile, nonflammable, thermally stable, and biodegradable. The catalyst was reused up to four consecutive cycles with high activity and selectivity. The fresh catalyst and recycle catalyst was well characterized by XPS anal. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methylbenzonitrile (cas: 60710-80-7Computed Properties of C8H8N2).

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. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Computed Properties of C8H8N2

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Nitrile – Wikipedia,
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Preparation of Tertiary Amines from Tris(2-cyanoethyl)amine Using Three Successive Cobalt-Catalyzed Electrophilic Aminations with Organozinc Halides was written by Grassl, Simon;Knochel, Paul. And the article was included in Organic Letters in 2020.Category: nitriles-buliding-blocks This article mentions the following:

A stepwise preparation of triple alkylated or arylated tertiary amines, starting from com. available tris(2-cyanoethyl)amine using three successive reaction sequences involving a selective oxidation (formation of an N-oxide followed by a Cope elimination) leading to an intermediate hydroxylamine, a benzoylation, and a cobalt-catalyzed electrophilic amination with organozinc halides is reported. In the experiment, the researchers used many compounds, for example, 3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1Category: nitriles-buliding-blocks).

3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1) belongs to nitriles. Nitrile carbon shifts are in the range of 115â€?25 ppm whereas in isonitriles the shifts are around 155â€?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.Category: nitriles-buliding-blocks

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Nitrile – Wikipedia,
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Emission characteristics of new laser dyes for the green and red spectral regions was written by Krymova, A. I.;Petukhov, V. A.;Popov, M. B.. And the article was included in Kvantovaya Elektronika (Moscow) in 1985.SDS of cas: 51473-74-6 This article mentions the following:

Emission characteristics were studies of solutions of certain new dyes from the classes of coumarins, naphthalimides, and benzanthrones under transverse pumping by the ruby laser 2nd-harmonic radiation. Most of the compounds showed laser action in the blue, green, and red spectral regions. A comparison was made of these substances with laser dyes widely used in the given spectral intervals. Compounds were found the lasing efficiency of which exceeds substantially that of uranin in the green region and that of Cresyl Violet in the red region and which are not inferior to them by photostability. In the experiment, the researchers used many compounds, for example, 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6SDS of cas: 51473-74-6).

7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6) 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. SDS of cas: 51473-74-6

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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

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Nitrile – Wikipedia,
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INCB050465 (Parsaclisib), a Novel Next-Generation Inhibitor of Phosphoinositide 3-Kinase Delta (PI3Kδ) was written by Yue, Eddy W.;Li, Yun-Long;Douty, Brent;He, Chunhong;Mei, Song;Wayland, Brian;Maduskuie, Thomas;Falahatpisheh, Nikoo;Sparks, Richard B.;Polam, Padmaja;Zhu, Wenyu;Glenn, Joseph;Feng, Hao;Zhang, Ke;Li, Yanlong;He, Xin;Katiyar, Kamna;Covington, Maryanne;Feldman, Patricia;Shin, Niu;Wang, Kathy He;Diamond, Sharon;Li, Yu;Koblish, Holly K.;Hall, Leslie;Scherle, Peggy;Yeleswaram, Swamy;Xue, Chu-Biao;Metcalf, Brian;Combs, Andrew P.;Yao, Wenqing. And the article was included in ACS Medicinal Chemistry Letters in 2019.Recommanded Product: 60025-09-4 This article mentions the following:

A medicinal chem. effort focused on identifying a structurally diverse candidate for phosphoinositide 3-kinase delta (PI3Kδ) led to the discovery of clin. candidate INCB050465 (20, parsaclisib). The unique structure of 20 contains a pyrazolopyrimidine hinge-binder in place of a purine motif that is present in other PI3Kδ inhibitors, such as idelalisib (1), duvelisib (2), and INCB040093 (3, dezapelisib). Parsaclisib (20) is a potent and highly selective inhibitor of PI3Kδ with drug-like ADME properties that exhibited an excellent in vivo profile as demonstrated through pharmacokinetic studies in rats, dogs, and monkeys and through pharmacodynamic and efficacy studies in a mouse Pfeiffer xenograft model. In the experiment, the researchers used many compounds, for example, 4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4Recommanded Product: 60025-09-4).

4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4) 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).Recommanded Product: 60025-09-4

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Nitrile – Wikipedia,
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Second harmonic generation from the single crystals of N-substituted 4-cyanoanilines was written by Hashimoto, H.;Okada, Y.;Okamoto, N.;Matsushima, R.. And the article was included in Journal of Luminescence in 2000.Category: nitriles-buliding-blocks This article mentions the following:

Six N-substituted derivatives of 4-cyanoaniline (pCA) were synthesized and their phys. and optical properties were examined in the search for 2nd-order nonlinear optical materials with enough crystal dimensions together with blue-light transparency. Among the derivatives examined, N-diphenylmethyl-pCA and N-2-naphthylmethyl-pCA afforded single crystals that lack a center of symmetry. Although the 2nd harmonic (SH) activities of these derivatives were not enough for the practical purposes, their cut-off wavelengths were shorter than 330 nm and showed sufficient blue-light transparency. Quant. prediction of the SH activity was also attempted. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Category: nitriles-buliding-blocks).

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. 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.Category: nitriles-buliding-blocks

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Stereoselective synthesis of spirocyclohexadiene-pyrazolones via organic base and/or hydrogen bonding assisted [3+3] annulation reactions was written by Sun, Bing-Bing;Zhang, Jun-Qi;Chen, Jun-Bo;Fan, Wei-Tai;Yu, Jie-Qiang;Hu, Jia-Ming;Wang, Xing-Wang. And the article was included in Organic Chemistry Frontiers in 2019.SDS of cas: 55490-87-4 This article mentions the following:

The 1,4-diazabicyclo[2.2.2]octane (DABCO)-catalyzed [3+3] cycloaddition reaction of α-arylidene pyrazolinones I (R¹ = Ph, 3-fluorophenyl, 2-naphthyl, 2-thienyl, etc.; R² = Ph, 4-methylphenyl, 4-methoxyphenyl, 4-fluorophenyl; R³ = Ph, 3-chlorophenyl, 4-cyanophenyl, 4-methylphenyl, 4-methoxyphenyl) and 2-benzylidenemalononitriles R⁴CH=C(CN)₂ (R² = Ph, 2-chlorophenyl, 9-anthracenyl, etc.) under mild reaction conditions has been reported, which afforded the spirocyclohexadiene-pyrazolones II in good yields with moderate to good diastereoselectivities. By the use of a cinchona alkaloid derived bifunctional squaramide-tertiary amine catalyst, an asym. variant of this [3 + 3] cycloaddition reaction has also been developed to provide optically active spirocyclohexadiene-pyrazolones bearing an all-carbon quaternary chiral center III in good yields with excellent enantioselectivities and moderate diastereoselectivities. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4SDS of cas: 55490-87-4).

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

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Nitrile – Wikipedia,
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Preparation of Tertiary Benzylic Nitriles from Aryl Fluorides was written by Caron, Stephane;Vazquez, Enrique;Wojcik, Jill M.. And the article was included in Journal of the American Chemical Society in 2000.Safety of 2-(4-Methoxyphenyl)-2-methylpropanenitrile This article mentions the following:

An efficient method for the addition of secondary nitriles to fluoroarenes was described. The reaction is specific to hexamethyldisilazane potassium salt, but proceeds with a variety of substrates. For example, the reaction of 1-fluoro-2-methoxybenzene with 2-methylpropanenitrile in the presence of hexamethyldisilazane potassium salt in toluene or THF gave 2-methoxy-α,α-dimethylbenzeneacetonitrile. In the experiment, the researchers used many compounds, for example, 2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5Safety of 2-(4-Methoxyphenyl)-2-methylpropanenitrile).

2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5) 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.Safety of 2-(4-Methoxyphenyl)-2-methylpropanenitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts