Category: 1483-54-1

Yang, Tao et al. published their research in European Journal of Organic Chemistry in 2019 | CAS: 1483-54-1

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

The Cascade Methylation/Cyclization of ortho-Cyanoarylacrylamides with Dicumyl Peroxide was written by Yang, Tao;Xia, Wen-Jin;Zhou, Bin;Xin, Yangchun;Shen, Yuehai;Li, Ya-Min. And the article was included in European Journal of Organic Chemistry in 2019.SDS of cas: 1483-54-1 This article mentions the following:

A radical cascade methylation/cyclization of ortho-cyanoarylacrylamides was developed by utilizing dicumyl peroxide as a methylation reagent. This transformation provides a simple and straight forward approach to methylated quinoline-2,4(1H,3H)-diones, and exhibits a wide substrate scope. Furthermore, this reaction could be readily scaled up. A possible mechanism is also proposed. In the experiment, the researchers used many compounds, for example, 2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1SDS of cas: 1483-54-1).

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Han, Jing et al. published their research in Advanced Synthesis & Catalysis in 2013 | CAS: 1483-54-1

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).Product Details of 1483-54-1

Copper(I)-Catalyzed Coupling Cyclization of Methyl Perfluoroalk-2-ynoates with 2-Aminobenzonitriles: Synthesis of 2-Perfluoroalkylated Quinolines was written by Han, Jing;Cao, Long;Bian, Linglin;Chen, Jie;Deng, Hongmei;Shao, Min;Jin, Zhijun;Zhang, Hui;Cao, Weiguo. And the article was included in Advanced Synthesis & Catalysis in 2013.Product Details of 1483-54-1 This article mentions the following:

An efficient route to 2-perfluoroalkylated quinoline derivatives through the copper(I)-mediated coupling-cyclization of 2-aminobenzonitriles with Me perfluoroalk-2-ynoates is described. Moderate to excellent yields have been achieved under mild conditions. E.g., in presence of CuBr and piperidine in DMSO, coupling-cyclization of 2-H2NC6H4CN and CF3C椤氬挵CO2Me gave 94% 2-perfluoroalkylated quinoline derivative (I). The reaction mechanism is also discussed. In the experiment, the researchers used many compounds, for example, 2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1Product Details of 1483-54-1).

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).Product Details of 1483-54-1

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Zhang, Chenhuan et al. published their research in Organic Letters in 2020 | CAS: 1483-54-1

2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1) 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. 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: 2-Amino-4-(trifluoromethyl)benzonitrile

Pd/Cu-Catalyzed Domino Cyclization/Deborylation of Alkene-Tethered Carbamoyl Chloride and 1,1-Diborylmethane was written by Zhang, Chenhuan;Wu, Xianqing;Wang, Chenchen;Zhang, Chengxi;Qu, Jingping;Chen, Yifeng. And the article was included in Organic Letters in 2020.Recommanded Product: 2-Amino-4-(trifluoromethyl)benzonitrile This article mentions the following:

Reported herein is a Pd/Cu cooperative-catalyzed dicarbofunctionalization of alkene-tethered carbamoyl chlorides with 1,1-diborylmethane. This cyclization/deborylation cascade strategy allows for the expedient formation of the versatile borylated 3,3-disubstituted oxindole skeleton, allowing for further functionalization via the derivatization of the C-B bond. In the experiment, the researchers used many compounds, for example, 2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1Recommanded Product: 2-Amino-4-(trifluoromethyl)benzonitrile).

2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1) 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. 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: 2-Amino-4-(trifluoromethyl)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Han, Jing et al. published their research in Advanced Synthesis & Catalysis in 2013 | CAS: 1483-54-1

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).Product Details of 1483-54-1

Copper(I)-Catalyzed Coupling Cyclization of Methyl Perfluoroalk-2-ynoates with 2-Aminobenzonitriles: Synthesis of 2-Perfluoroalkylated Quinolines was written by Han, Jing;Cao, Long;Bian, Linglin;Chen, Jie;Deng, Hongmei;Shao, Min;Jin, Zhijun;Zhang, Hui;Cao, Weiguo. And the article was included in Advanced Synthesis & Catalysis in 2013.Product Details of 1483-54-1 This article mentions the following:

An efficient route to 2-perfluoroalkylated quinoline derivatives through the copper(I)-mediated coupling-cyclization of 2-aminobenzonitriles with Me perfluoroalk-2-ynoates is described. Moderate to excellent yields have been achieved under mild conditions. E.g., in presence of CuBr and piperidine in DMSO, coupling-cyclization of 2-H2NC6H4CN and CF3CCCO2Me gave 94% 2-perfluoroalkylated quinoline derivative (I). The reaction mechanism is also discussed. In the experiment, the researchers used many compounds, for example, 2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1Product Details of 1483-54-1).

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).Product Details of 1483-54-1

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Zhang, Chenhuan et al. published their research in Organic Letters in 2020 | CAS: 1483-54-1

2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1) 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. 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: 2-Amino-4-(trifluoromethyl)benzonitrile

Pd/Cu-Catalyzed Domino Cyclization/Deborylation of Alkene-Tethered Carbamoyl Chloride and 1,1-Diborylmethane was written by Zhang, Chenhuan;Wu, Xianqing;Wang, Chenchen;Zhang, Chengxi;Qu, Jingping;Chen, Yifeng. And the article was included in Organic Letters in 2020.Recommanded Product: 2-Amino-4-(trifluoromethyl)benzonitrile This article mentions the following:

Reported herein is a Pd/Cu cooperative-catalyzed dicarbofunctionalization of alkene-tethered carbamoyl chlorides with 1,1-diborylmethane. This cyclization/deborylation cascade strategy allows for the expedient formation of the versatile borylated 3,3-disubstituted oxindole skeleton, allowing for further functionalization via the derivatization of the C-B bond. In the experiment, the researchers used many compounds, for example, 2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1Recommanded Product: 2-Amino-4-(trifluoromethyl)benzonitrile).

2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1) 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. 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: 2-Amino-4-(trifluoromethyl)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Tomioka, Yukihiko et al. published their research in Chemical & Pharmaceutical Bulletin in 1985 | CAS: 1483-54-1

2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1) 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.Synthetic Route of C8H5F3N2

Studies on aromatic nitro compounds. V. A simple one-pot preparation of o-aminoaroylnitriles from some aromatic nitro compounds was written by Tomioka, Yukihiko;Ohkubo, Kimiko;Yamazaki, Motoyoshi. And the article was included in Chemical & Pharmaceutical Bulletin in 1985.Synthetic Route of C8H5F3N2 This article mentions the following:

The reactions of aromatic nitro compounds I, II (R = H, R1 = NO2), and III (R, R1 = same, R2 = CF3, MeCO, PhCO, R3 = H ; R2 = R3 = CF3) with Et cyanoacetate and KOH in DMF followed by hydrolysis of the reaction mixture with HCl or NaOH gave the corresponding o-aminoaroylnitriles I–III (R = CN, R1 = NH2). Acetylation-cyclization reactions of the products were carried out. In the experiment, the researchers used many compounds, for example, 2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1Synthetic Route of C8H5F3N2).

2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1) 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.Synthetic Route of C8H5F3N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Deng, Guobo et al. published their research in Organic Letters in 2021 | CAS: 1483-54-1

2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. 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 2-Amino-4-(trifluoromethyl)benzonitrile

Assembly of Furazan-Fused Quinolines via an Expeditious Metal-Free [2+2+1] Radical Tandem Cyclization Process was written by Deng, Guobo;Zhong, Ronglin;Song, Jianxin;Choy, Pui Ying;Kwong, Fuk Yee. And the article was included in Organic Letters in 2021.Quality Control of 2-Amino-4-(trifluoromethyl)benzonitrile This article mentions the following:

A [2+2+1]-NO-segment-incorporating heteroannulative cascade is described. This versatile method, particularly using modular cyanoarylated ketimine substrates 2-CN-3-R-4-R1-5-R2C6HN=C(Me)Ar (Ar = 3-methylphenyl, 4-bromophenyl, thiophen-2-yl, etc.; R = H, Br; R1 = H, Br; R2 = H, Me, F, Cl, Br, MeO, CF3), allows efficient access to structurally diversified quinolines embedded with an oxadiazole core I. This metal-free protocol proceeds smoothly at 30°C, offers easy manipulation of substituents on the quinoline moiety, and tolerates a spectrum of functional groups. D. functional theory calculation revealed that the cyano moiety is crucial to facilitate the early cyclization step in this heteroannulation process and is different from the previously established late cyclization mechanistic interpretation. 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. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. 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 2-Amino-4-(trifluoromethyl)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Rahaim, Ronald J. Jr. et al. published their research in Synthesis in 2006 | CAS: 1483-54-1

2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1) 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. HPLC of Formula: 1483-54-1

Palladium-catalyzed silane/siloxane reductions in the one-pot conversion of nitro compounds into their amines, hydroxylamines, amides, sulfonamides, and carbamates was written by Rahaim, Ronald J. Jr.;Maleczka, Robert E. Jr.. And the article was included in Synthesis in 2006.HPLC of Formula: 1483-54-1 This article mentions the following:

A combination of palladium(II) acetate, aqueous potassium fluoride, and polymethylhydrosiloxane (PMHS) facilitates the room-temperature reduction of aromatic nitro compounds to anilines. These reactions tend to be quick (30 min), high-yielding, and tolerate a range of other functional groups. Replacement of PMHS/KF with triethylsilane allows for the reduction of aliphatic nitro compounds to their corresponding hydroxylamines. Depending on the substrate, both conditions can allow for the in situ conversion of the product amines into amides, sulfonamides, and carbamates. In the experiment, the researchers used many compounds, for example, 2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1HPLC of Formula: 1483-54-1).

2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1) 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. HPLC of Formula: 1483-54-1

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

September 28, 2021 News Sources of common compounds: 1483-54-1

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Amino-4-(trifluoromethyl)benzonitrile, its application will become more common.

Reference of 1483-54-1,Some common heterocyclic compound, 1483-54-1, name is 2-Amino-4-(trifluoromethyl)benzonitrile, molecular formula is C8H5F3N2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

EXAMPLE 4 9-Amino-1,4-methano-1,2,3,4-tetrahydro-6-trifluoromethylacridine To a solution of 2-amino-4-trifluoromethylbenzonitrile (12.8 g) in 50 ml of nitrobenzene was added freshly fused and pulverized ZnCl2 (14.1 g). This was heated at 50 C. fo 1 hour and to this mixture was added norcamphor (11.4 g). The reaction mixture was heated at 130 C. for 3 hours, after which it was cooled, diluted with ethyl ether and filtered. The resulting solid was partitioned between 2-butanone (MEK) and aqueous NH4 OH and the aqueous portion was extracted with MEK. The combined organics were washed with water, dried (satureatd NaCl, MgSO4) and concentrated to a solid which was triturated with ether/hexane to give 10.3 g of a white powder, m.p. 174-179 C. A 4.0 g portion was recrystallized from methanol/water to give 3.5 g of an analytically pure white powder, m.p. 175-178 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Amino-4-(trifluoromethyl)benzonitrile, its application will become more common.

Reference:
Patent; Hoechst-Roussel Pharmaceuticals Inc.; US5401749; (1995); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The origin of a common compound about 1483-54-1

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Amino-4-(trifluoromethyl)benzonitrile, and friends who are interested can also refer to it.

Reference of 1483-54-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 1483-54-1 name is 2-Amino-4-(trifluoromethyl)benzonitrile, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: In a 50 mL round bottom flask, a suspension of 2-aminoarylnitriles (10.0 mmol) in ethyl chloroformate(52.0 mmol, 5.0 mL) was refluxing for 6 h. After complete removal of excess ethyl chloroformate in vacuo (by forming azeotrope with toluene), the residue was recrystallized from cyclohexane (for mostsubstrates) to furnish the title compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Amino-4-(trifluoromethyl)benzonitrile, and friends who are interested can also refer to it.

Reference:
Article; Nguyen, Huy H.; Fettinger, James C.; Haddadin, Makhluf J.; Kurth, Mark J.; Tetrahedron Letters; vol. 56; 40; (2015); p. 5429 – 5433;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts