Category: nitriles-buliding-blocks

Radical Cation Salt-initiated Aerobic C-H Phosphorylation of N-Benzylanilines: Synthesis of 浼?Aminophosphonates was written by Jia, Xiaodong;Liu, Xiaofei;Yuan, Yu;Li, Pengfei;Hou, Wentao;He, Kaixuan. And the article was included in Chemistry – An Asian Journal in 2018.Safety of 4-(Benzylamino)benzonitrile This article mentions the following:

A radical cation salt-initiated phosphorylation of N-benzylanilines was realized through an aerobic oxidation of the sp³ C-H bond, providing a series of 浼?aminophosphonates in high yields. An investigation of the reaction scope revealed that this mild catalyst system is superior in good functional group tolerance and high reaction efficiency. The mechanistic study implied that the cleavage of the sp³ C-H bond was involved in the rate-determining step. 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. The R-C-N bond angle in and nitrile is 180鎺?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 锜? bond in the triple bond. 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.Safety of 4-(Benzylamino)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Asymmetric Reduction of Ketones by Phosphoric Acid Derived Catalysts was written by Zhang, Zuhui;Jain, Pankaj;Antilla, Jon C.. And the article was included in Angewandte Chemie, International Edition in 2011.Related Products of 101219-69-6 This article mentions the following:

Asym. reduction of ketones using a phosphoric acid derivative as the precatalyst was reported. Using catecholborane as a reducing agent, chiral secondary alcs. were produced with high levels of enantioselectivities over a resonably broad substrate scope. In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6Related Products of 101219-69-6).

(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閳ユ弲 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.Related Products of 101219-69-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Stable and reusable nanoscale Fe₂O₃-catalyzed aerobic oxidation process for the selective synthesis of nitriles and primary amides was written by Murugesan, Kathiravan;Senthamarai, Thirusangumurugan;Sohail, Manzar;Sharif, Muhammad;Kalevaru, Narayana V.;Jagadeesh, Rajenahally V.. And the article was included in Green Chemistry in 2018.Name: 2-Amino-3,5-dibromobenzonitrile This article mentions the following:

The sustainable introduction of nitrogen moieties in the form of nitrile or amide groups in functionalized mols. is of fundamental interest because nitrogen-containing motifs are found in a large number of life science mols., natural products and materials. Hence, the synthesis and functionalization of nitriles and amides from easily available starting materials using cost-effective catalysts and green reagents is highly desired. In this regard, herein the nanoscale iron oxide-catalyzed environmentally benign synthesis of nitriles and primary amides from aldehydes and aqueous ammonia in the presence of 1 bar O₂ or air was reported. Under mild reaction conditions, this iron-catalyzed aerobic oxidation process proceeds to synthesize functionalized and structurally diverse aromatic, aliphatic and heterocyclic nitriles. Addnl., applying this iron-based protocol, primary amides have also been prepared in a water medium. In the experiment, the researchers used many compounds, for example, 2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5Name: 2-Amino-3,5-dibromobenzonitrile).

2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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.Name: 2-Amino-3,5-dibromobenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Redox-Active Reagents for Photocatalytic Generation of the OCF₃ Radical and (Hetero)Aryl C-H Trifluoromethoxylation was written by Zheng, Weijia;Lee, Johnny W.;Morales-Rivera, Cristian A.;Liu, Peng;Ngai, Ming-Yu. And the article was included in Angewandte Chemie, International Edition in 2018.HPLC of Formula: 55406-13-8 This article mentions the following:

The trifluoromethoxy (OCF₃) radical is of great importance in organic chem. Yet, the catalytic and selective generation of this radical at room temperature and pressure remains a longstanding challenge. Herein, the design and development of a redox-active cationic reagent (1) that enables the formation of the OCF₃ radical in a controllable, selective, and catalytic fashion under visible-light photocatalytic conditions is reported. More importantly, the reagent allows catalytic, intermol. C-H trifluoromethoxylation of a broad array of (hetero)arenes and biorelevant compounds Exptl. and computational studies suggest single electron transfer (SET) from excited photoredox catalysts to 1 resulting in exclusive liberation of the OCF₃ radical. Addition of this radical to (hetero)arenes gives trifluoromethoxylated cyclohexadienyl radicals that are oxidized and deprotonated to afford the products of trifluoromethoxylation. In the experiment, the researchers used many compounds, for example, 3-Methylthiophene-2-carbonitrile (cas: 55406-13-8HPLC of Formula: 55406-13-8).

3-Methylthiophene-2-carbonitrile (cas: 55406-13-8) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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: 55406-13-8

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Potassium-Functionalized Graphitic Carbon Nitride Supported on Reduced Graphene Oxide as a Sustainable Catalyst for Knoevenagel Condensation was written by Bahuguna, Ashish;Kumar, Ashwani;Chhabra, Tripti;Kumar, Ajay;Krishnan, Venkata. And the article was included in ACS Applied Nano Materials in 2018.Reference of 55490-87-4 This article mentions the following:

A nanocomposite of potassium-functionalized graphitic carbon nitride (KGCN) and reduced graphene oxide (RGO) was fabricated by a facile hydrothermal method and used as a heterogeneous catalyst for Knoevenagel condensation and sustainable synthesis of aryl substituted chromenes. The prepared KGCN-RGO nanocomposite catalyst has been characterized by using various techniques, such as powder X-ray diffraction technique (PXRD), Fourier transform IR spectroscopy, SEM, transmission electron microscopy, thermogravimetric anal., and BET surface area anal. After detailed characterization, the nanocomposite was used as a heterogeneous catalyst to synthesize various aryl substituted chromenes in ethanol. The developed KGCN-RGO nanocatalyst also rendered good recyclability for the explored catalytic reactions. In addition, a high value of atom economy and a low value of E-factor are also key highlights of this green and sustainable catalytic protocol. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Reference of 55490-87-4).

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.Reference of 55490-87-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A Dynamic Three-Dimensional Covalent Organic Framework was written by Ma, Yun-Xiang;Li, Zhi-Jun;Wei, Lei;Ding, San-Yuan;Zhang, Yue-Biao;Wang, Wei. And the article was included in Journal of the American Chemical Society in 2017.Reference of 55490-87-4 This article mentions the following:

A guest-induced reversible crystal-structure transformation is identified in a new 3D covalent organic framework (COF) by comprehensive analyses using powder X-ray diffraction, organic vapor sorption isotherm, and ¹²⁹Xe NMR spectroscopy. The revolving imine bond in interpenetrating 3D networks is uncovered as the key to the dynamic behavior, the potential applications of which are illustrated by gas separation and heterogeneous catalysis, thus paving the way to the design of stimuli-responsive and multifunctional COF materials. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Reference of 55490-87-4).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) belongs to nitriles. Nitrile carbon shifts are in the range of 115閳?25 ppm whereas in isonitriles the shifts are around 155閳?65 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.Reference of 55490-87-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Experimental and Computational Studies on Cp*^CyRh(III)/KOPiv-Catalyzed Intramolecular Dehydrogenative Cross-Couplings for Building Eight-Membered Sultam/Lactam Frameworks was written by Li, Liping;Gao, Hui;Sun, Ming;Zhou, Zhi;Yi, Wei. And the article was included in Organic Letters in 2020.Quality Control of 2-Amino-3-chlorobenzonitrile This article mentions the following:

Described herein is an unusual Cp*CyRh(III)-catalyzed intramol. site-specific aryl C-H annulation, a highly chemoselective protocol providing direct access to eight-membered sultams/lactams I (R¹ = H, 9-Me, 7-Cl, etc; R² = Me, Et, Ph, 4-Br-C₆H₄; R³ = H, 2-Me, 3-OMe, etc.)and II (X = CO, PO-Ph; Ar = Ph, 2-Me-C₆H₄, Naph, Py, etc.) with broad substrate/functional group tolerance. Exptl. and computational studies reveal that such a transformation involves a unique PivOH-assisted aryl C-H activation/alkene insertion/灏?H elimination/hydrogen-transfer process involving the Rh(III)-hydride species as the active intermediate with the concomitant release of H₂ as the major byproduct, thus enabling the developed Cp*CyRh(III) catalysis with redox-neutral and highly atom-economical features. In the experiment, the researchers used many compounds, for example, 2-Amino-3-chlorobenzonitrile (cas: 53312-77-9Quality Control of 2-Amino-3-chlorobenzonitrile).

2-Amino-3-chlorobenzonitrile (cas: 53312-77-9) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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.Quality Control of 2-Amino-3-chlorobenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Pyrazole NNRTIs 3: Optimisation of physicochemical properties was written by Mowbray, Charles E.;Corbau, Romuald;Hawes, Michael;Jones, Lyn H.;Mills, James E.;Perros, Manos;Selby, Matthew D.;Stupple, Paul A.;Webster, Rob;Wood, Anthony. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2009.Reference of 104798-53-0 This article mentions the following:

Our efforts to reduce overall lipophilicity and increase ligand-lipophilicity efficiency (LLE) by modification of the 3- and 5-substituents of pyrazole I, a novel non-nucleoside HIV reverse transcriptase inhibitor (NNRTI) prototype were unsuccessful. In contrast replacement of the substituted benzyl group with corresponding phenylthio or phenoxy groups resulted in marked improvements in potency, ligand efficiency (LE) and LLE. In the experiment, the researchers used many compounds, for example, 2-Fluoro-5-hydroxybenzenecarbonitrile (cas: 104798-53-0Reference of 104798-53-0).

2-Fluoro-5-hydroxybenzenecarbonitrile (cas: 104798-53-0) 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.Reference of 104798-53-0

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Piperazine-Grafted Magnetic Reduced Graphene Oxide (Fe₃O₄@rGO-NH) as a Reusable Heterogeneous Catalyst for Gewald Three-Component Reaction was written by Rezaei-Seresht, Esmail;Bakhshi-Noroozi, Morteza;Maleki, Behrooz. And the article was included in Polycyclic Aromatic Compounds in 2021.Application of 70291-62-2 This article mentions the following:

In recent years, interesting phys. and chem. properties of graphene oxide (GO) have led to a great deal of excitement in the chem. One of the most promising results is the use of GO and the functionalized GOs as heterogeneous catalysts in organic synthesis. In this work, GO was functionalized with piperazine (GO-NH), converted to magnetic GO-NH by incorporating Fe₃O₄ particles into GO-NH (Fe₃O₄@rGO-NH), and then reduced with hydrazine hydrate to yield piperazine-grafted magnetic reduced graphene oxide (Fe₃O₄@rGO-NH). The obtained Fe₃O₄@rGO-NH was used as a heterogeneous catalyst in the Gewald three-component reaction between some aldehydes or ketones, sulfur, and malononitrile or Et cyanoacetate. The catalyst showed good activity for various starting materials, easy separation from the reaction mixture using an ordinary magnet and reusability. Also, the catalyst was used six times without significant loss of activity. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Application of 70291-62-2).

2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2) 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. 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.Application of 70291-62-2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Efficient cyanation of aryl bromides with K₄[Fe(CN)₆] catalyzed by a palladium-indolylphosphine complex was written by Yeung, Pui Yee;Tsang, Chun Pui;Kwong, Fuk Yee. And the article was included in Tetrahedron Letters in 2011.Formula: C8H8N2 This article mentions the following:

This study describes a general palladium-catalyzed cyanation of aryl bromides using K₄[Fe(CN)₆] as the cyanide surrogate. The reactions can be successfully conducted under mild reaction conditions (at 50鎺矯) in mixed solvents (water/MeCN = 1:1) without any surfactant additives, and afford the desired aryl nitriles in good-to-excellent yields. Particularly noteworthy is that this system allows the mildest reaction temperature reported so far for palladium-catalyzed cyanation of aryl bromides with K₄[Fe(CN)₆] source in general. Common functional groups, including keto, aldehyde, free amine, and heterocyclic substrates are compatible under this system. Interestingly, the phosphine ligands bearing -PCy₂ moiety, which usually show excellent activity in aryl halide couplings, are found less effective than the corresponding ligands with -PPh₂ group. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methylbenzonitrile (cas: 60710-80-7Formula: C8H8N2).

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. Formula: C8H8N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts