Month: January 2023

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

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

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

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

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

Uses of 2-amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile in the synthesis of heterocyclic compounds with anticonvulsant, behavioral and CNS antidepressant activities was written by El-Sharkawy, K. A.;El-Sayed, N. N. E.;Zaki, M. Y.. And the article was included in International Research Journal of Pure and Applied Chemistry in 2012.COA of Formula: C8H8N2S This article mentions the following:

A reaction of the cyclopenta[b]thiophene with Ph isothiocyanate gave a thiourea derivative The synthesis of the target compounds was achieved using 2-amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile as a starting material. The latter was treated with the active methylene compounds to provide pyrimidine derivatives N-acylation reaction was achieved using acetic anhydride as a reactant. N-(3-Cyano-5,6-dihydro-4H-cyclopenta[b]thien-2-yl)acetamide was used as a reactant for the synthesis of several derivatives thereof. Finally treatment of N-(3-cyano-5,6-dihydro-4H-cyclopenta[b]thien-2-yl)acetamide with different activated nitrile derivatives, hydrazine derivatives gave thienopyridine derivatives and thienopyrimidine derivatives The newly synthesized compounds were tested for anticonvulsant, behavioral and CNS antidepressant activities. The title compounds thus formed included a thienopyrimidine hydrazine imine (I). In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2COA of Formula: C8H8N2S).

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. 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.COA of Formula: C8H8N2S

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electrochemical Benzylic C-H Functionalization with Isocyanides was written by Tang, Shanyu;Guillot, Regis;Grimaud, Laurence;Vitale, Maxime R.;Vincent, Guillaume. And the article was included in Organic Letters in 2022.Safety of 2-(4-Methoxyphenyl)-2-methylpropanenitrile This article mentions the following:

Author report the challenging direct carbamoylation or cyanation of benzylic C(sp³)-H bonds with an isocyanide via an electrochem. process giving rise to structures which are encountered in several biol. relevant compounds and drugs. This transformation proceeds in mild conditions without the need of any external oxidant and avoids the necessity to start from a prefunctionalized benzylic substrate or the deployment of the cation pool method. Anodic oxidation of the benzylic position and subsequent addition of the isocyanide leads to the formation of a C-C bond and to a nitrilium cation which hydrolysis yields alpha-aryl acetamide derivatives, while elimination of a t-Bu cation delivers alpha-aryl acetonitrile derivatives 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. 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 2-(4-Methoxyphenyl)-2-methylpropanenitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reductive cyanation of organic chlorides using CO₂ and NH₃ via Triphos-Ni(I) species was written by Dong, Yanan;Yang, Peiju;Zhao, Shizhen;Li, Yuehui. And the article was included in Nature Communications in 2020.Quality Control of 2-Amino-4-(trifluoromethyl)benzonitrile This article mentions the following:

The reductive cyanation of organic chlorides RCl (R = C₆H₅, naphthalen-1-yl, cyclohexyl, etc.) using CO₂/NH₃ as the electrophilic CN source has been described. The use of tridentate phosphine ligand Triphos allows for the nickel-catalyzed cyanation of a broad array of aryl and aliphatic chlorides to produce the desired nitrile products RCN in good yields, and with excellent functional group tolerance. Cheap and bench-stable urea was also shown as suitable CN source, suggesting promising application potential. Mechanistic studies imply that Triphos-Ni(I) species are responsible for the reductive C-C coupling approach involving isocyanate intermediates. This method expands the application potential of reductive cyanation in the synthesis of functionalized nitrile compounds under cyanide-free conditions, which is valuable for safe synthesis of (isotope-labeled) drugs. In the experiment, the researchers used many compounds, for example, 2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1Quality Control of 2-Amino-4-(trifluoromethyl)benzonitrile).

2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1) 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. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Quality Control of 2-Amino-4-(trifluoromethyl)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Nitration of 2-cyanothiophene was written by Reynaud, Pierre;Delaby, Raymond. And the article was included in Bulletin de la Societe Chimique de France in 1955.Recommanded Product: 42137-24-6 This article mentions the following:

Fuming HNO₃ (d. 1.49) added dropwise to 2-cyanothiophene in cold Ac₂O (10-12°) gives 80% 4-nitro-2-cyanothiophene (I), m. 102° after recrystallization; 5-nitro-2-cyanothiophene (II), m. 45°, also forms in 20% yield. The reaction is kept easily under control by keeping the temperature below 20° with an ice-salt bath, and the isolation of the isomers presents no difficulty. I refluxed 2 h. with concentrated HCl forms 4-nitro-2-thiophenecarboxylic acid (III), m. 154°, after recrystallization I dissolves easily in HCl, and III crystallizes on cooling. This method also offers a simple method of preparation of 3-nitrothiophene, which is obtained in 77% yield from III by decarboxylation with Cu and quinoline in a tube in a metal bath; CO₂ is evolved at 160°. In the experiment, the researchers used many compounds, for example, 4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6Recommanded Product: 42137-24-6).

4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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. Recommanded Product: 42137-24-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Covalent-assembly based fluorescent probes for detection of hNQO1 and imaging in living cells was written by Han, Jialing;Cheng, Longhao;Zhu, Ya;Xu, Xiaowei;Ge, Chaoliang. And the article was included in Frontiers in Chemistry (Lausanne, Switzerland) in 2020.Computed Properties of C14H14N2O2 This article mentions the following:

Human NAD(P)H: quinone oxidoreductase (hNQO1) is an important biomarker for human malignant tumors. Detection of NQO1 accurately is of great significance to improve the early diagnosis of cancer and prognosis of cancer patients. In this study, based on the covalent assembly strategy, hNQO1-activated fluorescent probes 1 and 2 are constructed by introducing coumarin precursor 2-cyano-3-(4-(diethylamino)-2-hydroxyphenyl) acrylic acid and self-immolative linkers. Under reaction with hNQO1 and NADH, turn-on fluorescence appears due to in-situ formation of the organic fluorescent compound 7-diethylamino-3-cyanocoumarin, and fluorescent intensity changes significantly. Probe 1 and 2 for detection of hNQO1 are not interfered by other substances and have low toxicity in cells. In addition to quant. detection of hNQO1 in vitro, they have also been successfully applied to fluorescent imaging in living cells. In the experiment, the researchers used many compounds, for example, 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6Computed Properties of C14H14N2O2).

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. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Computed Properties of C14H14N2O2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts