Category: nitriles-buliding-blocks

Ruthenium-Catalyzed Direct Reductive Amination in HCOOH/NEt₃ Mixture was written by Zhu, Mengping. And the article was included in Catalysis Letters in 2014.Reference of 10282-32-3 This article mentions the following:

Abstract: A one-pot direct reductive amination of aldehydes with primary and secondary amines using Noyori’s catalyst (η⁶-arene)Ru(H)TsDPEN in neat HCOOH/NEt₃ mixture has been developed. The catalyst formed in situ allows full conversion of aldehydes with high selectivities towards the desired amine products within hours or even minutes at room temperature For aromatic aldehydes, both 5:2 and 5:3 HCOOH/NEt₃ mixtures prove to be suitable reaction media, with the former affording higher selectivities while the latter leading to much faster reaction rates. For aliphatic aldehydes, the 5:3 HCOOH/NEt₃ mixture gives much higher selectivities due to the minimal loss from aldol condensation. This method has great application potential for the synthesis of amine products given the mild conditions. Graphical Abstract: [Figure not available: see full text.]. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Reference of 10282-32-3).

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. 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.Reference of 10282-32-3

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Discovery and Characterization of MAPK-activated Protein Kinase-2 Prevention of Activation Inhibitors was written by Cumming, John G.;Debreczeni, Judit E.;Edfeldt, Fredrik;Evertsson, Emma;Harrison, Martin;Holdgate, Geoffrey A.;James, Michael J.;Lamont, Scott G.;Oldham, Keith;Sullivan, Jane E.;Wells, Stuart L.. And the article was included in Journal of Medicinal Chemistry in 2015.Quality Control of 3-Amino-4-methylbenzonitrile This article mentions the following:

Two structurally distinct series of novel, MAPK-activated kinase-2 prevention of activation inhibitors have been discovered by high throughput screening. Preliminary structure-activity relationship (SAR) studies revealed substructural features that influence the selective inhibition of the activation by p38α of the downstream kinase MK2 in preference to an alternative substrate, MSK1. Enzyme kinetics, surface plasmon resonance (SPR), 2D protein NMR, and x-ray crystallog. were used to determine the binding mode and the mol. mechanism of action. The compounds bind competitively to the ATP binding site of p38α but unexpectedly with higher affinity in the p38α-MK2 complex compared with p38α alone. This observation is hypothesized to be the origin of the substrate selectivity. The two lead series identified are suitable for further investigation for their potential to treat chronic inflammatory diseases with improved tolerability over previously studied p38α inhibitors. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methylbenzonitrile (cas: 60710-80-7Quality Control of 3-Amino-4-methylbenzonitrile).

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Dynamic modeling of consecutive reactions: application to the acrylonitrile amination was written by Kadri, Brahim;Fabre, Bernard;Accary, Armand;Kessler, Mathieu. And the article was included in Canadian Journal of Chemical Engineering in 1998.Quality Control of 3,3′,3”-Nitrilotripropanenitrile This article mentions the following:

When dealing with optimal control problems to maximize the selectivity of reactions for fine chem. synthesis, representative kinetic and thermodn. models should be available. While literature appears to be very extensive on theor. approaches to solve the problem, examples presenting complete models of chem. transformations are scarce. This paper presents the identification of consecutive reactions carried out in a batch reactor. Material and energy balances, satisfying dynamical state evolutions in the temperature range 20-60°C are deduced, for concentrations of acrylonitrile ranging up to 1.6 kmol·m^-3. The stoichiometric network is simplified into two reactions, one reversible and one irreversible. Reaction enthalpies are measured from isothermal runs conducted in the RC1 heat-flow calorimeter from Mettler Toledo. In the experiment, the researchers used many compounds, for example, 3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1Quality Control of 3,3′,3”-Nitrilotripropanenitrile).

3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1) 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. 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.Quality Control of 3,3′,3”-Nitrilotripropanenitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Photoinduced Copper-Catalyzed Asymmetric C(sp³)-H Alkynylation of Cyclic Amines by Intramolecular 1,5-Hydrogen Atom Transfer was written by Guo, Rui;Xiao, Haijing;Li, Sijia;Luo, Yixin;Bai, Jiahui;Zhang, Mengzhen;Guo, Yinlong;Qi, Xiaotian;Zhang, Guozhu. And the article was included in Angewandte Chemie, International Edition in 2022.SDS of cas: 53312-77-9 This article mentions the following:

The development of a mild and general method for C(sp³)-H functionalization of cyclic amines has been an ongoing challenge. In this work, authors describe the copper-catalyzed enantioselective C(sp³)-H alkynylation of unactivated cyclic 2-iodo-benzamide under photo-irradiation by intramol. 1,5-hydrogen atom transfer (HAT). The employment of a new bisoxazoline diphenylamine ligand, in conjunction with 1,1′-bi-2-naphthol, which significantly improved the reduction potential of the copper complex, was the key to success of this chem. Mechanistic and computational studies supported that the new copper complex served the dual role as a photoredox and coupling catalyst, the reaction went through a radical process, and the intramol. 1,5-HAT process was involved in the rate-limiting step. Apart from the broad substrate scope including unprecedented benzocyclic amines, this method also showed excellent diastereoselectivity in 2-monosubstituted cyclic amines via substrate control. In the experiment, the researchers used many compounds, for example, 2-Amino-3-chlorobenzonitrile (cas: 53312-77-9SDS of cas: 53312-77-9).

2-Amino-3-chlorobenzonitrile (cas: 53312-77-9) 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 conventional organic reductions, nitrile is reduced by treatment with lithium aluminium hydride to the amine. Reduction to the imine followed by hydrolysis to the aldehyde takes place in the Stephen aldehyde synthesis, which uses stannous chloride in acid.SDS of cas: 53312-77-9

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A general post-synthetic modification approach of amino-tagged metal-organic frameworks to access efficient catalysts for the Knoevenagel condensation reaction was written by Luan, Yi;Qi, Yue;Gao, Hongyi;Andriamitantsoa, Radoelizo S.;Zheng, Nannan;Wang, Ge. And the article was included in Journal of Materials Chemistry A: Materials for Energy and Sustainability in 2015.Synthetic Route of C18H10N2 This article mentions the following:

Four common transition metal derived metal-organic frameworks have been extensively investigated as heterogeneous catalyst supports for Knoevenagel condensation reactions [IRMOF-3, Cr-MIL-101-NH₂, UiO-66-NH₂, and Al-MIL-53-NH₂]. A simple post-synthetic modification strategy was employed for the rapid and facile introduction of a primary alkyl amino group. The resulting novel MOF-RNH₂ catalysts showed greatly enhanced Knoevenagel condensation reactivities towards a variety of aldehyde electrophiles [R = -CH₂CH(Me)-]. IRMOF-3 proved to be an unsuitable heterogeneous catalyst support due to its fragile nature upon treatment with bases. The novel zirconium based UiO-66-NH-RNH₂ and chromium based Cr-MIL-101-NH-RNH₂ materials showed excellent catalytic reactivities, while being highly convenient to synthesize. The basic catalytic activity was further extended to the Henry reaction, and excellent catalytic reactivity was achieved. The size-selectivity was also studied to show that the Knoevenagel condensation occurred inside of the porous structure of the MOF catalyst. The recycling properties of zirconium, aluminum and chromium derived MOFs were evaluated and zirconium based UiO-66 and chromium based Cr-MIL-101 showed excellent catalytic efficiency after five reaction cycles. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Synthetic Route of C18H10N2).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) 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.Synthetic Route of C18H10N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Liquid crystalline compounds with positive dielectric anisotropy was written by Bezborodov, V. S.;Lapanik, V. I.;Mikhalyonok, S. G.. And the article was included in Zhidkie Kristally i Ikh Prakticheskoe Ispol’zovanie in 2015.HPLC of Formula: 82380-17-4 This article mentions the following:

In this paper we present the results of the investigations of liquid crystalline (LC) compounds with pos. dielec. anisotropy. The anal. of the properties of polar mesomorphic compounds and the electrooptical and dynamic parameters of the LC compositions based on them has shown that the polar liquid crystalline 1,3,2- dioxaborinane derivatives have several advantages in comparison with other analogous polar compounds They are characterized by a low formation temperature and a wide temperature range of the nematic phase, and allow preparation of liquid crystalline compositions with a low threshold voltage and shorter switching times. In the experiment, the researchers used many compounds, for example, 2-Bromo-4-hydroxybenzonitrile (cas: 82380-17-4HPLC of Formula: 82380-17-4).

2-Bromo-4-hydroxybenzonitrile (cas: 82380-17-4) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. 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.HPLC of Formula: 82380-17-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Development of potential manufacturing routes for substituted thiophenes – preparation of halogenated 2-thiophenecarboxylic acid derivatives as building blocks for a new family of 2,6-dihaloaryl 1,2,4-triazole insecticides was written by Hull, John W. Jr.;Romer, Duane R.;Podhorez, David E.;Ash, Mezzie L.;Brady, Christine H.. And the article was included in Beilstein Journal of Organic Chemistry in 2007.Recommanded Product: 55406-13-8 This article mentions the following:

Potential manufacturing routes to three halogenated 2-thiophenecarboxylic acid derivatives, namely, 4-bromo-3-methyl-2-thiophenecarbonyl chloride, 3,4,5-trichloro-2-thiophenecarbonyl chloride, and 3,4,5-trichloro-2-thiophenecarbonitrile, from com. available thiophene raw materials have been developed and demonstrated on a laboratory scale. A one-pot bromination/debromination procedure developed for 3-methylthiophene gave 2,4-dibromo-3-methylthiophene. Carboxylic acid functionality was then introduced either by a Grignard metalation followed by carbonation with CO₂, or by a palladium catalyzed carbonylation procedure under CO pressure. The vapor phase chlorination of 2-thiophenecarbonitrile with chlorine gas at 500 °C with an average residence time of 6 s gave 3,4,5-trichloro-2-thiophenecarbonitrile in a 69% distilled yield, a process that was carried out on a multi-kilogram scale in the laboratory Finally, a route for the preparation of 3,4,5-trichloro-2-thiophenecarbonyl chloride was developed from tetrachlorothiophene via either a lithiation reaction with n-butyllithium in MTBE, or by a previously reported Grignard method using 1,2-dibromoethane as activator, followed by carbonation of the anion with CO₂ to give the trichloro-2-thiophenecarboxylic acid, which was readily converted to the corresponding acid chloride with SOCl₂. In the experiment, the researchers used many compounds, for example, 3-Methylthiophene-2-carbonitrile (cas: 55406-13-8Recommanded Product: 55406-13-8).

3-Methylthiophene-2-carbonitrile (cas: 55406-13-8) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. In conventional organic reductions, nitrile is reduced by treatment with lithium aluminium hydride to the amine. Reduction to the imine followed by hydrolysis to the aldehyde takes place in the Stephen aldehyde synthesis, which uses stannous chloride in acid.Recommanded Product: 55406-13-8

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Enantioselective catalytic reduction of ketones using C₂-symmetric diamines as chiral ligands was written by Gamez, Patrick;Fache, Fabienne;Mangeney, Pierre;Lemaire, Marc. And the article was included in Tetrahedron Letters in 1993.Quality Control of (R)-4-(1-Hydroxyethyl)benzonitrile This article mentions the following:

The catalytic enantioselective reduction of various prochiral ketones is reported using C₂-sym. diamines as ligands. Up to 99% e.e. at 100% conversion are obtained. In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6Quality Control of (R)-4-(1-Hydroxyethyl)benzonitrile).

(R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6) 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 conventional organic reductions, nitrile is reduced by treatment with lithium aluminium hydride to the amine. Reduction to the imine followed by hydrolysis to the aldehyde takes place in the Stephen aldehyde synthesis, which uses stannous chloride in acid.Quality Control of (R)-4-(1-Hydroxyethyl)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis of new iminocoumarins and their transformations into N-chloro and hydrazono compounds was written by Volmajer, Julija;Toplak, Renata;Leban, Ivan;Majcen Le Marechal, Alenka. And the article was included in Tetrahedron in 2005.Application In Synthesis of 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile This article mentions the following:

The Knoevenagel reaction between 2-hydroxybenzaldehydes and active methylene compounds (malononitrile and Et cyanoacetate) produced iminocoumarins, e.g., I, and/or coumarins. In order to study the reactivity of the prepared iminocoumarins, chlorination and reaction with N-nucleophiles were studied. In the experiment, the researchers used many compounds, for example, 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6Application In Synthesis of 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile).

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Thermochemistry of substituted thiophenecarbonitrile derivatives was written by Ribeiro da Silva, Manuel A. V.;Santos, Ana Filipa L. O. M.. And the article was included in Journal of Chemical Thermodynamics in 2008.Electric Literature of C6H5NS This article mentions the following:

The standard (p° = 0.1 MPa) molar energies of combustion in oxygen of 2-thiophenecarbonitrile, 3-thiophenecarbonitrile, 2-thiopheneacetonitrile, 3-thiopheneacetonitrile, and 3-methyl-2-thiophenecarbonitrile were measured, at T = 298.15 K, by rotating-bomb calorimetry. The standard molar enthalpies of vaporization of these compounds at T = 298.15 K were determined using high temperature Calvet microcalorimetry. These values were used to derive the standard molar enthalpies of formation of the title compounds in their crystalline and gaseous phases. The standard molar enthalpies of formation for the title compounds in the gaseous state were derived and the results are interpreted in terms of structural effects. In the experiment, the researchers used many compounds, for example, 3-Methylthiophene-2-carbonitrile (cas: 55406-13-8Electric Literature of C6H5NS).

3-Methylthiophene-2-carbonitrile (cas: 55406-13-8) 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.Electric Literature of C6H5NS

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts