Category: nitriles-buliding-blocks

Precision Polyethylene: Changes in Morphology as a Function of Alkyl Branch Size was written by Rojas, Giovanni;Inci, Bora;Wei, Yuying;Wagener, Kenneth B.. And the article was included in Journal of the American Chemical Society in 2009.Safety of 2-Cyclohexylacetonitrile This article mentions the following:

Metathesis polycondensation chem. has been employed to control the crystalline morphol. of a series of 11 precision-branched polyethylene structures, the branch being placed on each 21st carbon and ranging in size from a Me group to an adamantyl group. The crystalline unit cell is shifted from orthorhombic to triclinic, depending upon the nature of the precision branch. Further, the branch can be positioned either in the crystalline phase or in the amorphous phase of polyethylene, a morphol. change dictated by the size of the precision branch. This level of morphol. control is accomplished using step polymerization chem. to produce polyethylene rather than conventional chain polymerization techniques. Doing so requires the synthesis of a series of unique sym. diene monomers incorporating the branch in question, followed by ADMET polymerization and hydrogenation to yield the precision-branched polyethylene under study. Exhaustive structure characterization of all reaction intermediates as well as the precision polymers themselves is presented. A clear change in morphol. was observed for such polymers, where small branches (Me and ethyl) are included in the unit cell, while branches equal to or greater in mass than Pr are excluded from the crystal. When the branch is excluded from the unit cell, all such polyethylene polymers possess essentially the same melting temperature, regardless of the size of the branch, even for the adamantyl branch. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Safety of 2-Cyclohexylacetonitrile).

2-Cyclohexylacetonitrile (cas: 4435-14-7) 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.Safety of 2-Cyclohexylacetonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Transfer hydrogenation of nitroarenes into anilines by palladium nanoparticles via dehydrogenation of dimethylamine borane complex was written by Patil, Nilesh M.;Bhosale, Manohar A.;Bhanage, Bhalchandra M.. And the article was included in RSC Advances in 2015.Application In Synthesis of 3-Amino-4-methylbenzonitrile This article mentions the following:

This work reports a simple and highly efficient protocol for reduction of nitroarenes to corresponding amines via dehydrogenation of dimethylamine borane using palladium nanoparticles (Pd NPs) as a versatile heterogeneous catalyst. The facile approach for the synthesis of Pd NPs within 15 min in aqueous medium has been reported. The Pd NPs were well characterized using various anal. techniques such as X-ray diffraction (XRD), field emission gun scanning electron microscope (FEG-SEM), transmission electron microscopy (TEM), energy dispersive X-ray spectrum (EDAX) and X-ray photoelectron spectrum (XPS). The developed catalytic system uses environmentally benign dimethylamine borane as a reducing agent which is highly stable, water soluble and nontoxic. The various amines were synthesized from nitroarenes in excellent yields within 10-60 min at room temperature The catalyst was reused up to four successive cycles without significant loss in its catalytic activity. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methylbenzonitrile (cas: 60710-80-7Application In Synthesis of 3-Amino-4-methylbenzonitrile).

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.Application In Synthesis of 3-Amino-4-methylbenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Cobalt encapsulated in N-doped graphene sheet for one-pot reductive amination to synthesize secondary amines was written by Liu, Lin;Li, Wenxiu;Qi, Ran;Zhu, Qingqing;Li, Jing;Fang, Yuzhen;Kong, Xiangjin. And the article was included in Molecular Catalysis in 2021.Product Details of 10282-32-3 This article mentions the following:

In this study, an efficient N-doped graphene sheet-coated cobalt catalyst (Co@CN-800) was developed through a simple pyrolysis process, which could gave 99.5% yield of N-benzylaniline by one-pot reductive amination of nitrobenzene with benzaldehyde during at least 5 cycles. Catalyst characterization and control experiments confirmed that the robust catalytic performance of the catalyst is probably due to the synergy effect of in situ generated Co-Nx encapsulated in N-doped graphene layer and appropriate meso-pore structure. Addnl., the substrate adaptability of the catalyst was proved since a variety of corresponding secondary amines RCH₂NHR¹ (R = C₆H₅, 4-pyridyl, cyclohexyl, etc.; R¹ = C₆H₅, 4-FC₆H₄, cyclohexyl, etc.) were smoothly obtained under relatively mild conditions, which makes the secondary amine synthesis strategy based on Co@CN-800 shows excellent application prospect. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Product Details of 10282-32-3).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) 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.Product Details of 10282-32-3

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A facile synthesis of trifluoromethylamines by oxidative desulfurization-fluorination of dithiocarbamates was written by Kanie, Kiyoshi;Mizuno, Katsuya;Kuroboshi, Manabu;Hiyama, Tamejiro. And the article was included in Bulletin of the Chemical Society of Japan in 1998.Quality Control of 4-(Benzylamino)benzonitrile This article mentions the following:

Trifluoromethylamines are easily synthesized from dithiocarbamates by a reagent system consisting of tetrabutylammonium dihydrogen trifluoride and an N-halo imide under mild conditions. When this reaction was applied to dithiocarbamates ArN(R)CS₂Me at higher temperatures, the trifluoromethylation was accompanied by halogen substitution at the p-position of the Ar group. The synthesis of trifluoromethyl-substituted adenosine is also described. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Quality Control of 4-(Benzylamino)benzonitrile).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. 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.Quality Control of 4-(Benzylamino)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Disarming the alkoxide trap to access a practical FeCl₃ system for borrowing-hydrogen N-alkylation was written by Ye, Zongren;Yang, Zhenjie;Yang, Chenhui;Huang, Ming;Xu, Xianfang;Ke, Zhuofeng. And the article was included in Organic Chemistry Frontiers in 2022.Related Products of 10282-32-3 This article mentions the following:

Borrowing hydrogen N-alkylation is one of the most valuable transformations in organic synthesis, with high selectivity and at. economy. The general non-noble metal catalysts for borrowing hydrogen usually have limitations on operational convenience or catalytic efficiency. In particular, the development of practical and mild Fe(III) catalysis is a big challenge due to the alkoxide trap in terms of d-wall issues. Inspired by the theor. design, utilizing an in situ reaction strategy to overcome the alkoxide trap of Fe(III), authors present here a practical in situ ferric chloride and bis-(N-heterocyclic carbene) (bis-NHC) system for the borrowing-hydrogen N-alkylation of amines by alcs. under mild reaction conditions, attributed to the merits of bis-NHC in strong-field ligands, strong σ-donation and π-back-donation, and the trans effect. This system was applied to a wide range of alcs. and amines. Through comprehensive experiments and DFT calculations, the mechanism of the reaction was studied, which highlighted the roles of strong-field ligands, strong σ-donation and π-back-donation, and the trans effect by bis-NHC in ensuring the in situ reduction of Fe(III) to Fe(II) and triggering the borrowing of hydrogen under mild conditions. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Related Products of 10282-32-3).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) 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.Related Products of 10282-32-3

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Intramolecular nucleophilic aromatic substitution reaction of 2-carboxamido-3-arylquinazolin-4-ones and its application to the synthesis of secondary aryl amines was written by Fuwa, Haruhiko;Kobayashi, Toshitake;Tokitoh, Takashi;Torii, Yukiko;Natsugari, Hideaki. And the article was included in Synlett in 2004.Reference of 10282-32-3 This article mentions the following:

A novel intramol. nucleophilic aromatic substitution reaction of 2-carboxamido-3-arylquinazolin-4-one derivatives induced by base treatment and its application to the expeditious synthesis of secondary aryl amines, including diaryl amines, are described. 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. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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 10282-32-3

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Single-Crystalline, Size, and Orientation Controllable Nanowires and Ultralong Microwires of Organic Semiconductor with Strong Photoswitching Property was written by Jiang, Lang;Fu, Yanyan;Li, Hongxiang;Hu, Wenping. And the article was included in Journal of the American Chemical Society in 2008.COA of Formula: C18H10N2 This article mentions the following:

Single-crystalline, precise size-controlled nanowires and ultralong microwires with lengths reaching several millimeters of 2-anthracen-9-ylmethylenemalonitrile were prepared in large scale by cast assembly. The size and d. of the nanowires and microwires could be controlled by simply adjusting the concentration of the compound in casting solutions More importantly, the formation of these nanowires and microwires showed no substrate and solvent dependence and was orientation controllable. Highly reproducible and sensitive photoresponse characteristics were observed in these nanowires and microwires. Fast and reversible photoswitchers based on multiple or individual single-crystal microwires were fabricated via “multi times gold wire mask moving” technique with switch ratio over 100. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4COA of Formula: C18H10N2).

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. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).COA of Formula: C18H10N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Catalytic Asymmetric Addition of Organolithium Reagents to Aldehydes was written by Veguillas, Marcos;Sola, Ricard;Shaw, Luke;Macia, Beatriz. And the article was included in European Journal of Organic Chemistry in 2016.Related Products of 101219-69-6 This article mentions the following:

Herein we report an efficient catalytic system for the titanium-promoted enantioselective addition of organolithium reagents to aldehydes, based on chiral Ar-BINMOL ligands. Unprecedented yields and enantioselectivities are achieved in the alkylation reactions of aliphatic aldehydes. Remarkably, methyllithium can be added to a wide variety of aromatic and aliphatic aldehydes, providing versatile chiral Me carbinol units in a simple one-pot procedure under mild conditions and in very short reaction times. 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. 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. 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.Related Products of 101219-69-6

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

ZIF-8 nanoparticles as an efficient and reusable catalyst for the Knoevenagel synthesis of cyanoacrylates and 3-cyanocoumarins was written by Kolmykov, Oleksii;Chebbat, Nassima;Commenge, Jean-Marc;Medjahdi, Ghouti;Schneider, Raphael. And the article was included in Tetrahedron Letters in 2016.Related Products of 51473-74-6 This article mentions the following:

Zeolitic imidazolate framework (ZIF-8) particles with an average size of ca. 355 nm and a sp. surface area of 1786 m².g^-1 were used as an heterogenous catalyst for the Knoevenagel synthesis of α,β-unsaturated cyanoesters and 3-cyanocoumarins. The preparation of 3-cyanocoumarins was efficiently achieved using DMF as the solvent and conducting the condensation at 80°. When the reaction was performed in ethanol, only the intermediates α,β-unsaturated cyanoesters were obtained. The ZIF-8 catalyst could be reused up to five times without any degradation in activity. SEM and XRD analyses demonstrated the high stability of ZIF-8 crystals during the recycling test. In the experiment, the researchers used many compounds, for example, 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6Related Products of 51473-74-6).

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Pharmacophore modeling, 3D-QSAR, synthesis, and anti-lung cancer evaluation of novel thieno[2,3-d][1,2,3]triazines targeting EGFR was written by Elrayess, Ranza;Abdel Aziz, Yasmine M.;Elgawish, Mohamed S.;Elewa, Marwa;Elshihawy, Hosam A.;Said, Mohamed M.. And the article was included in Archiv der Pharmazie (Weinheim, Germany) in 2020.Safety of 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile This article mentions the following:

Two series of thieno[2,3-d][1,2,3]triazine derivatives were designed, synthesized, and biol. evaluated as potential epidermal growth factor receptor (EGFR) inhibitors targeting the non-small-cell lung cancer cell line H1299. Most of the synthesized compounds displayed IC₅₀ values ranging from 25 to 58 nM against H1299, which are superior to that of gefitinib (40μM). 3-(5,6,7,8-Tetrahydro-7H-cyclohexa[4:5]thieno[2,3-d]-1,2,3-triazin-4-ylamino)benzene-1,3-diamine (6b) achieved the highest cytotoxic activity against H1299 with an IC₅₀ value of 25 nM; it had the ability to decrease the EGFR concentration in H1299 cells from 7.22 to 2.67 pg/mL. In vitro, the IC₅₀ value of compound 6b was 0.33 nM against EGFR, which is superior to that of gefitinib at 1.9 nM and erlotinib at 4 nM. The three-dimensional quant. structure-activity relationships and mol. modeling studies revealed comparable binding modes of compound 6b, gefitinib, and erlotinib in the EGFR active site. The in silico ADME (absorption, distribution, metabolism, and excretion) prediction parameters of this compound revealed promising pharmacokinetic and physicochem. properties. Moreover, DFT (d. functional theory) calculations showed the high reactivity of compound 6b toward the EGFR compared with other compounds The designed compound 6b might serve as an encouraging lead compound for the discovery of promising anti-lung cancer agents targeting EGFR. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Safety of 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile).

2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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.Safety of 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts