Month: January 2023

Palladium-catalyzed amination of aryl bromides using temperature-controlled microwave heating was written by Wan, Yiqian;Alterman, Mathias;Hallberg, Anders. And the article was included in Synthesis in 2002.HPLC of Formula: 10282-32-3 This article mentions the following:

Fast Pd-catalyzed aminations of aryl bromides were conducted in a non-inert reaction medium with temperature-controlled microwave heating. With a reaction time of 4 min at 130° or 180°, both electron-rich and electron-deficient aryl bromides reacted with various amines to provide fair to good yields of the corresponding secondary and tertiary anilines. As an example the amination of 4-bromobenzonitrile with imidazole is presented. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3HPLC of Formula: 10282-32-3).

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Design, synthesis and biological evaluation of new series of hexahydroquinoline and fused quinoline derivatives as potent inhibitors of wild-type EGFR and mutant EGFR (L858R and T790M) was written by Shaheen, Mennatallah A.;El-Emam, Ali A.;El-Gohary, Nadia S.. And the article was included in Bioorganic Chemistry in 2020.Product Details of 55490-87-4 This article mentions the following:

New series of hexahydroquinoline and fused quinoline derivatives were designed and synthesized. The thirty seven new compounds were screened for in vitro antitumor activity against HepG2, HCT-116 and MCF-7 cancer cells. Results indicated that certain compounds, including I, have the strongest potency against the three cancer cells, and they were further screened for in vitro cytotoxicity against A431 and H1975 cancer cells, as well as WI38 and WISH normal cells. Results revealed that I potently inhibited the growth of H1975 cells harboring EGFR^T790M mutation (IC₅₀ = 1.32 ± 0.2μM) over A431 cells overexpressing EGFR^WT (IC₅₀ = 4.96 ± 0.3μM). Moreover, the seven compounds displayed low cytotoxicity against the tested normal cells. The seven potent antitumor compounds were examined for their ability to inhibit the activity of EGFR^WT. The attained data manifested that I has remarkable EGFR^WT inhibitory activity (IC₅₀ = 0.083 ± 0.002μM) compared to erlotinib (IC₅₀ = 0.067 ± 0.002μM). Compound I was further studied for its enzymic inhibitory activity against other eight human kinases, and it displayed outstanding inhibitory activity against EGFR^L858R and EGFR^T790M mutants (IC₅₀ = 0.053 ± 0.002, 0.026 ± 0.001μM, resp.), as well as JAK3 (IC₅₀ = 0.069 ± 0.003μM). Anal. of cell cycle evidenced that I induces cell cycle arrest in G2/M and pre-G1 phases in the tested cancer cells. In addition, cancer cell death induced by I was proved to take place via apoptosis supported by elevated Bax/Bcl-2 ratio in the tested cancer cells. Moreover, docking results confirmed the good binding interactions of I with EGFR^WT, EGFR^L858R, EGFR^T790M and JAK3, which came in agreement with the results of in vitro enzyme assay. Further, I is predicted to have good oral absorption, good drug-likeness properties and low toxicity risks in human. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Product Details of 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. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Product Details of 55490-87-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A new naturally occurring polyamine containing a quaternary ammonium nitrogen was written by Oshima, Tairo;Hamasaki, Nobuko;Senshu, Mitsuko;Kakinuma, Katsumi;Kuwajima, Isao. And the article was included in Journal of Biological Chemistry in 1987.Related Products of 7528-78-1 This article mentions the following:

A new polyamine, tetrakis(3-aminopropyl)ammonium, N⁺(CH₂CH₂CH₂NH₂)₄, was identified in cells of an extreme thermophile, T. thermophilus. This compound was chem. synthesized and its chem. properties were coincident with those of the amine isolated from the thermophile. In the experiment, the researchers used many compounds, for example, 3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1Related Products of 7528-78-1).

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. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Related Products of 7528-78-1

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Amination of benzylic C-H bonds by arylazides catalyzed by Co^II-porphyrin complexes: A synthetic and mechanistic study was written by Ragaini, Fabio;Penoni, Andrea;Gallo, Emma;Tollari, Stefano;Li Gotti, Claudia;Lapadula, Marta;Mangioni, Enrica;Cenini, Sergio. And the article was included in Chemistry – A European Journal in 2003.Computed Properties of C14H12N2 This article mentions the following:

Co^II-porphyrin complexes catalyze the reaction of aromatic azides (ArN₃) with hydrocarbons that contain a benzylic group (ArR¹R²CH) to give the corresponding amines (ArR¹R²C-N-HAr). When at least one of the R substituents is hydrogen, the catalytic reaction proceeds further to give the imine ArRC:NAr in good yields. The reaction mechanism has been investigated. The reaction proceeds through a reversible coordination of the arylazide to the Co^II-porphyrin complex. This unstable adduct can either react with the hydrocarbon in the rate-determining step or decompose by a unimol. mechanism to afford a putative “nitrene” complex, which reacts with more azide, but not with the hydrocarbon, to afford the byproduct diaryldiazene. The kinetics of the catalytic reaction have been investigated for a range of azides and substituted toluenes. Aryl azides with electron-withdrawing substituents react at a faster rate and a good correlation is found between the log(k) and the Taft parameters. On the other hand, an excellent correlation between the logarithm of the rate for substituted toluenes relative to that of toluene and a radical parameter (σ_JJ) alone was found, with no significant contribution by polar parameters. An explanation has been proposed for this anomalous effect and for the very high isotopic effect (k_H/k_D = 14) found. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Computed Properties of C14H12N2).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) belongs to nitriles. Nitrile carbon shifts are in the range of 115�25 ppm whereas in isonitriles the shifts are around 155�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.Computed Properties of C14H12N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Affinity capacities and migration tendencies. V. The affinity capacity of the anisyl radical according to the dehydration of dialkylanisyl glycols and the isomerization of the corresponding ethylene oxides by heat was written by Tiffeneau, M.;Levy, Jeanne;Weill, Paul. And the article was included in Bulletin de la Societe Chimique de France in 1931.Recommanded Product: 5351-07-5 This article mentions the following:

It has been found, by the hydrolysis of oxazoles, studies of the halochromism of triarylcarbinols as well as by the cleavage of ketones under the influence of NaNH₂, that the affinity capacity or force attachment of the anisyl radical is 2-7 times greater than that of the Ph radical. Dehydration of the glycols PhCH(OH)C(OH)Me₂ and PhCH(OH)C(OH)(CH₂Ph)₂ and isomerization of the corresponding ethylene oxides have shown that the affinity capacities of the various radicals can be arranged in the order of decreasing magnitude, Me₂ > Ph > (PhCH₂)₂. The product obtained in the isomerization by heat of the oxide of MeOC₆H₄CH:CMe₂ (C. A. 20, 2850) has insufficiently characterized and was considered to be an aldehyde. This conclusion implied that the affinity capacity of anisyl was less than that of Me₂. A further study has shown that the product is a ketone, MeOC₆H₄CHMeAc formed according to the rearrangement, from which it is concluded that the affinity capacity of anisyl exceeds that of Me₂. Although it thus becomes futile to compare the affinity capacities of anisyl with those of other acyclic radicals, results of experiments made on the constitution of iodohydrins, the isomerization of ethylene oxides and the dehydration of glycols on the series AnCH:CR₂ (where An = anisyl and R = Me, Et, Pr and PhCH₂) are reported. The fixation of HOI on MeOC₆H₄CH:CMe₂ gives MeOC₆H₄CH(OH)CIMe₂, which with dry KOH yields anisyldimethylacetaldehyde I, MeOC₆H₄CMe₂CHO, b₁₈ 140-5°; oxime, m. 104-5°; anisyldimethylacetonitrile, b₂₀ 165-70°. I furnishes a rare example of a trisubstituted aldehyde which can form a bisulfite compound The product of the isomerization of anisyldimethylethylene oxide and of the dehydration of anisyldimethyl glycol is 2-anisyl-3-butanone, b. 260-5°; semicarbazone, 183-4°. The dehydration at 150° of 1-anisyl-2-ethyl-1-butanol, prepared from MeOC₆H₄MgBr and 3-ethyl-4-butanol, yields anisyldiethylethylene, MeOC₆H₄CH:CEt₂, b₁₄ 1340, n_D¹⁵ 1.532, d₀ 0.98, oxidized by BzO₂H to the ethylene oxide (II), b₁₆ 156-8°, n_D¹⁵ 1.515. Distillation of II in the presence of infusorial earth or pumice soaked in H₂SO₄ completely isomerizes it to 3-anisyl-4-hexanone (III), b₁₉ 158-60, n_D¹⁵ 1.523, d₀ 1.034 (semscarbazone, m. 138°), identical with the product prepared from the Na derivative of 1-anisyl-2-butanone with EtBr. The dehydration by heat or 50% H₂SO₄ of anisyldiethylglycol, MeOC₆H₄CH(OH)C(OH)Et₂, m. 78-9°, also produces III. Anisyldipropylethylene oxide, b₁₃ 162-5°, n_D¹⁵ 1.1512, d₀ 0.995, prepared by the action of Bz₂OH on anisyldipropylethylene, b₁₆ 162-5°, n_D¹⁵ 1.528, d₀ 0.953, is isomerized by distillation to 4-anisyl-5-octanone, b. 280°, n_D¹⁵ 1.511, d. 0.984 (semicarbazone, m. 97°), which is also formed by the dehydration by heat or 25% H₂SO₄ of anisyldipropylglycol, m. 93-4°, obtained in 50% yields by the action of 4 mols. of PrMgBr on 1 mol. of Et anisylglycolate. The distillation at reduced pressure of anisyldibenzylethylene oxide gives 2-anisyl-1,4-diphenyl-3-butanone (IV), stable to cold concentrated H₂SO₄ and to the action of alc. KOH at 150°, m. 75°; oxime, m. 95° (Ac derivative, m. 61-2°); isonitroso derivative, m. 153-4°. With PhCH₂MgCl, IV is transformed into anisyltribenzylethanol, m. 105-6°. The direct benzylation of acetylanisole, AcC₆H₄OMe, gives dibenzylacetylanisole, (PhCH₂)₂CHCOC₆H₄OMe, m. 93-5° (semicarbazone, m. 179-80°), not identical with IV. The latter is also formed by the dehydration of anisyldibenzyl glycol, prepared from PhCH₂MgBr and Et anisylglycolate. In the experiment, the researchers used many compounds, for example, 2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5Recommanded Product: 5351-07-5).

2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5) belongs to nitriles. Nitrile carbon shifts are in the range of 115�25 ppm whereas in isonitriles the shifts are around 155�65 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.Recommanded Product: 5351-07-5

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A novel thiocarbamide functionalized graphene oxide supported bimetallic monodisperse Rh-Pt nanoparticles (RhPt/TC@GO NPs) for Knoevenagel condensation of aryl aldehydes together with malononitrile was written by Sen, Betul;Akdere, Esma Hazal;Savk, Aysun;Gultekin, Emine;Parali, Ozge;Goksu, Haydar;Sen, Fatih. And the article was included in Applied Catalysis, B: Environmental in 2018.Reference of 55490-87-4 This article mentions the following:

It is shown in this study that the graphene oxide can be mainly functionalized with a single species of sulfur and can be reduced to form a graphene which is functionalized with monothiol at the same time. By the help of thiocarbamide-functionalized graphene oxide (TC@GO) the monodisperse rhodium/platinum nanoparticles (RhPt/TC@GO NPs) have been synthesized as promising catalysts for the Knoevenagel condensation to benzylidenemalononitrile derivatives of aryl aldehydes. The monodisperse RhPt/TC@GO NPs have been prepared via a facile method. The novel thiocarbamide-functionalized graphene oxide (TC@GO) supported rhodium/platinum nanoparticles (RhPt/TC@GO NPs) are identified by characterization techniques such as the Raman spectroscopy, high resolution transmission electron microscopy (HRTEM), transmission electron microscopy (TEM), X-ray diffraction (XRD) and XPS. The spectroscopic and morphol. studies of the monodisperse RhPt/TNM@GO NPs indicate the highly crystalline form, well dispersity, ultrafine structure and colloidally stable NPs. After fully characterization of prepared nanoparticles, the novel nanocatalysts have been tried for the Knoevenagel condensation to benzylidenemalononitrile derivatives of aryl aldehydes and show excellent catalytic activity and a yield over 99% by the reaction at room temperature within 8-35 min in the presence of malononitrile and derivatives of aldehyde. As a result, the prepared nanocomposites exhibit very good heterogeneous catalyst properties for Knoevenagel condensation reactions. 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. 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.Reference of 55490-87-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis of Carbamoyl Fluorides Using a Difluorophosgene Surrogate Derived from Difluorocarbene and Pyridine N-Oxides was written by Cadwallader, Dusty;Tiburcio, Tristan R.;Cieszynski, George A.;Le, Christine M.. And the article was included in Journal of Organic Chemistry in 2022.Name: 4-(Benzylamino)benzonitrile This article mentions the following:

The authors report a method for the synthesis of carbamoyl fluorides from secondary amines using bench-stable, inexpensive, and readily accessible starting materials that, when combined, yield a surrogate for toxic difluorophosgene (COF₂) gas. In contrast to state-of-the-art methods for the synthesis of carbamoyl fluorides, the current protocol does not require the use of pre-functionalized substrates, the preparation of light-, temperature-, and/or moisture-sensitive chems., nor the application of explosive fluorinating reagents. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Name: 4-(Benzylamino)benzonitrile).

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. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Name: 4-(Benzylamino)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

1,3-diethynylallenes: stable monomers, length-defined oligomers, asymmetric synthesis, and optical resolution was written by ter Wiel, Matthijs K. J.;Odermatt, Severin;Schanen, Patrick;Seiler, Paul;Diederich, Francois. And the article was included in European Journal of Organic Chemistry in 2007.Related Products of 5351-07-5 This article mentions the following:

A series of differently substituted 1,3-diethynylallenes (DEAs) have been synthesized, confirming that the previously introduced construction protocols tolerate a variety of functional groups. The new DEAs bear at least one polar group to facilitate enantiomer separations on chiral stationary phases and to allow further functionalization. They are thermally and environmentally stable compounds since bulky substituents next to the cumulene moiety suppress the tendency to undergo [2 + 2] cyclodimerization. A series of length-defined oligomers were obtained as mixtures of stereoisomers by oxidative coupling of a monomeric DEA under Glaser-Hay conditions. The electronic absorption data indicate a lack of extended π-electron conjugation across the oligomeric backbone due to the orthogonality of the allenic π-systems. Remarkably, even complex mixtures of stereoisomers only yield one single set of NMR signals, which under-lines the low stereodifferentiation in acyclic allenoacetylenic structures. Optical resolution of DEAs represents an amazing challenge, and preliminary results on the anal. level are reported. Asym. synthesis by Pd-mediated S_N2′-type cross-coupling of an alkyne to an optically pure bispropargylic precursor opens another promising route to optically active allenes with stereoselectivities currently reaching up to 78% ee. In the experiment, the researchers used many compounds, for example, 2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5Related Products of 5351-07-5).

2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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 5351-07-5

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis and in vitro acetylcholinesterase and butrylcholinesterase inhibitory activity of tacrine (cognex) derivatives was written by Gregor, Vlad E.;Emmerling, Mark R.;Lee, Chitase;Moore, Catherine J.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 1992.Product Details of 53312-77-9 This article mentions the following:

Chlorosubstituted derivatives of tacrine, I (X = H, 5-, 6-, 7-, 8-Cl, n = 0), and of 1,4-methylenetacrine, I (n = 1), and their in vitro acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activities are described. Thus, 2-aminobenzonitriles II (X = H, 3-, 4-, 5-, 6-Cl) cyclized with cyclohexanone or norcamphor to give I (n = 0, 1), resp. The most potent analogs are 6-chlorotacrine I (X = 6-Cl, n = 0) in AChE and 7-chlorotacrine I (X = 7-Cl, n = 0) in BChE inhibition. In the experiment, the researchers used many compounds, for example, 2-Amino-3-chlorobenzonitrile (cas: 53312-77-9Product Details of 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. 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.Product Details of 53312-77-9

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Fast and efficient bromination of aromatic compounds with ammonium bromide and oxone was written by Naresh, Mameda;Kumar, Macharla Arun;Reddy, Marri Mahender;Swamy, Peraka;Nanubolu, Jagadeesh Babu;Narender, Nama. And the article was included in Synthesis in 2013.COA of Formula: C7H4Br2N2 This article mentions the following:

A highly efficient, rapid and regioselective protocol was developed for the ring bromination of aromatic compounds under mild conditions with ammonium bromide as a source of bromine source and Oxone (potassium peroxysulfate) as an oxidant. No metal catalyst or acidic additive is required. A variety of aromatic compounds, including methoxy, hydroxy, amino, and alkyl arenes, reacted smoothly to give the corresponding monobrominated products in good to excellent yields in very short reaction times. Moreover, dibromination of deactivated anilines to give the corresponding dibromides proceeded in high yields. Interestingly, 1-(2-naphthyl)ethanone provided a ring-brominated product. In the experiment, the researchers used many compounds, for example, 2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5COA of Formula: C7H4Br2N2).

2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).COA of Formula: C7H4Br2N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts