53312-77-9 Archives - Nitriles-buliding-blocks

Li, Liping et al. published their research in Organic Letters in 2020 | CAS: 53312-77-9

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

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).

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Luo, Fen-Tair et al. published their research in Tetrahedron in 2006 | 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. 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. Synthetic Route of C7H5ClN2

The novel reaction of ketones with o-oxazoline-substituted anilines was written by Luo, Fen-Tair;Ravi, Vija K.;Xue, Cuihua. And the article was included in Tetrahedron in 2006.Synthetic Route of C7H5ClN2 This article mentions the following:

A variety of ketones reacted with o-oxazoline-substituted anilines in the presence of catalytic amount of p-toluenesulfonic acid in dry n-butanol to form 4-amino-substituted quinolines or 4-quinolones in fair to good yields. In the experiment, the researchers used many compounds, for example, 2-Amino-3-chlorobenzonitrile (cas: 53312-77-9Synthetic Route of C7H5ClN2).

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Zhao, Wei et al. published their research in ChemCatChem in 2016 | CAS: 53312-77-9

2-Amino-3-chlorobenzonitrile (cas: 53312-77-9) 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. 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. Category: nitriles-buliding-blocks

Quinazolinones from o-Aminobenzonitriles by One-Pot Sequential Selective Hydration/Condensation/Acceptorless Dehydrogenation Catalyzed by an Iridium Complex was written by Zhao, Wei;Liu, Pengcheng;Li, Feng. And the article was included in ChemCatChem in 2016.Category: nitriles-buliding-blocks This article mentions the following:

A new strategy for the direct synthesis of quinazolinones from o-aminobenzonitriles was proposed and accomplished. In the presence of [Cp*IrCl₂]₂ (Cp*=pentamethylcyclopentadienyl), a variety of desirable products was obtained easily through the one-pot sequential selective hydration/condensation/acceptorless dehydrogenation. This protocol was highly attractive because it used readily available starting materials, has a high atom efficiency, good to excellent yields, and minimal consumption of chems. and energy. Notably, this research exhibited new potential for the development of transition-metal-catalyzed one-pot sequential reactions that involve acceptorless dehydrogenation. In the experiment, the researchers used many compounds, for example, 2-Amino-3-chlorobenzonitrile (cas: 53312-77-9Category: nitriles-buliding-blocks).

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Li, Zhenhua et al. published their research in Heterocycles in 2012 | CAS: 53312-77-9

2-Amino-3-chlorobenzonitrile (cas: 53312-77-9) 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.Application In Synthesis of 2-Amino-3-chlorobenzonitrile

Facile and efficient cyclization of anthranilonitrile to 2,4-dichloroquinazoline by bis(trichloromethyl) carbonate and catalytic amount triphenylphosphine oxide was written by Li, Zhenhua;Wu, Danli;Zhong, Weihui. And the article was included in Heterocycles in 2012.Application In Synthesis of 2-Amino-3-chlorobenzonitrile This article mentions the following:

2,4-Dichloroquinazolines were synthesized by the cyclization of anthranilonitrile using bis(trichloromethyl)carbonate with the aid of catalytic amount of Ph₃PO at 120 °C. This method was also applied to the synthesis of 2,4-dichlorothieno[2,3-d]pyrimidine. The plausible mechanism was presented. In the experiment, the researchers used many compounds, for example, 2-Amino-3-chlorobenzonitrile (cas: 53312-77-9Application In Synthesis of 2-Amino-3-chlorobenzonitrile).

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Wan, Yin-Bo et al. published their research in Organic Letters in 2022 | CAS: 53312-77-9

2-Amino-3-chlorobenzonitrile (cas: 53312-77-9) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.SDS of cas: 53312-77-9

Highly Enantioselective Iridium-Catalyzed Hydrogenation of o-Amidophenyl Ketones Enabled by 1,2-Diphenylethylenediamine-Derived P,N,N-Ligands with Tertiary Amine Terminus was written by Wan, Yin-Bo;Hu, Xiang-Ping. And the article was included in Organic Letters in 2022.SDS of cas: 53312-77-9 This article mentions the following:

A readily available and highly modular class of chiral P,N,N-ligands based on a structurally flexible nonchiral phosphine-amine framework with an optically active 1,2-diphenylethylenediamine unit bearing a tertiary amine terminus as the chiral source were developed and successfully applied in the Ir-catalyzed asym. hydrogenation of o-amidophenyl ketones. These tridentate P,N,N-ligands exhibited excellent activity, enantioselectivity, and substrate tolerance, thus furnishing various optically active o-amidobenzhydrols in up to 99% yields and with >99% ee. The utility of this protocol was proven by synthetically diverse product transformation and highly enantioselective production of a rice plant growth regulator, (S)-inabenfide. In the experiment, the researchers used many compounds, for example, 2-Amino-3-chlorobenzonitrile (cas: 53312-77-9SDS of cas: 53312-77-9).

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Guo, Rui et al. published their research in Angewandte Chemie, International Edition in 2022 | 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

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

Analyzing the synthesis route of C7H5ClN2

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 53312-77-9.

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 53312-77-9, name is 2-Amino-3-chlorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., name: 2-Amino-3-chlorobenzonitrile

To a solution of 2-amino-3-chlorobenzonitrile (5.0 g, 32.9 mmol) in dry DMF (60 mL) was added NaH (1.97 g, 60%, 49.3 mmol) at 0 C. Then, the mixture was stirred at 0 C for 15 min. Mel (4.67 g, 32.9 mmol) was added and the mixture was stirred at rt for 2 hrs. The reaction solution was quenched with saturated NH4C1 solution, diluted with EtOAc (200 mL), washed with H20 (2x) and brine (2x), dried (Na2S04), filtered, and concentrated. The residue was purified by silica gel column chromatography (EtOAc/PE=0~5%) to give 3-chloro-2- (methylamino)benzonitrile (4.8 g, 88%) as a white solid. ESI-MS (EI+, m/z): 167.0 [M+1]+.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 53312-77-9.

Reference:
Patent; DISCOVERYBIOMED, INC.; SCHWIEBERT, Erik; STREIFF, John; DIXON, John; GAO, Hongwu; WO2014/152213; (2014); A2;,
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Some scientific research about 53312-77-9

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Adding a certain compound to certain chemical reactions, such as: 53312-77-9, name is 2-Amino-3-chlorobenzonitrile, belongs to nitriles-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 53312-77-9, Product Details of 53312-77-9

BH3THF complex (1M in THF, 26 mL, 26.2 mmol) was added ina dropwise manner at 0 C (ice-bath) to 2-amino-3-chlorobenzonitrile (7) (1.00 g, 6.6 mmol) under an N2 atmosphere.The stirred reaction mixture was heated at reflux overnight,allowed to cool to room temperature, quenched by addition of HCl(6 N, to pH 2), and heated at reflux for 30 min. The reaction mixturewas allowed to cool to room temperature and then cooled to 0 C(ice-bath) and basified with NaOH (3 M, to pH 12) and extractedwith CH2Cl2 (2 40 mL). The combined organic portion waswashed with H2O (100 mL), dried (MgSO4) and evaporated underreduced pressure to afford 0.93 g (90%) of 8 as a sticky solid. IRspectroscopy indicated the absence of a characteristic cyano band

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Abdelkhalek, Ahmed S.; Musayev, Faik N.; Iyer, Kavita A.; Hemanth, Prithvi; Safo, Martin K.; Dukat, Ma?gorzata; Journal of Molecular Structure; vol. 1202; (2020);,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts