Category: 68385-95-5

Murugesan, Kathiravan et al. published their research in Green Chemistry in 2018 | CAS: 68385-95-5

2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5) 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.Name: 2-Amino-3,5-dibromobenzonitrile

Stable and reusable nanoscale Fe2O3-catalyzed aerobic oxidation process for the selective synthesis of nitriles and primary amides was written by Murugesan, Kathiravan;Senthamarai, Thirusangumurugan;Sohail, Manzar;Sharif, Muhammad;Kalevaru, Narayana V.;Jagadeesh, Rajenahally V.. And the article was included in Green Chemistry in 2018.Name: 2-Amino-3,5-dibromobenzonitrile This article mentions the following:

The sustainable introduction of nitrogen moieties in the form of nitrile or amide groups in functionalized mols. is of fundamental interest because nitrogen-containing motifs are found in a large number of life science mols., natural products and materials. Hence, the synthesis and functionalization of nitriles and amides from easily available starting materials using cost-effective catalysts and green reagents is highly desired. In this regard, herein the nanoscale iron oxide-catalyzed environmentally benign synthesis of nitriles and primary amides from aldehydes and aqueous ammonia in the presence of 1 bar O2 or air was reported. Under mild reaction conditions, this iron-catalyzed aerobic oxidation process proceeds to synthesize functionalized and structurally diverse aromatic, aliphatic and heterocyclic nitriles. Addnl., applying this iron-based protocol, primary amides have also been prepared in a water medium. In the experiment, the researchers used many compounds, for example, 2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5Name: 2-Amino-3,5-dibromobenzonitrile).

2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5) 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.Name: 2-Amino-3,5-dibromobenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Bergman, Jan et al. published their research in Tetrahedron in 1986 | CAS: 68385-95-5

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 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.Electric Literature of C7H4Br2N2

Synthesis of quinazolines was written by Bergman, Jan;Brynolf, Anna;Elman, Bjoern;Vuorinen, Eino. And the article was included in Tetrahedron in 1986.Electric Literature of C7H4Br2N2 This article mentions the following:

Reaction of RMgX (R = Me, Et, Ph, 4-MeC6H4, Me2CH, Bu; X = Cl, Br, iodo) with 2-H2NC6H4CN gave the intermediate 2-H2NC6H4CR:N– (I), which were cyclized to quinazolines by reaction with carbonyl compounds (e.g., acid chlorides, anhydrides, formates, and oxalates). Reaction of I with aldehydes, e.g. PhCHO, gave 1,2-dihydroquinazolines, which were readily dehydrogenated. Reaction of I with ClCO2Me gave 4-phenyl-2-quinazolinone, which was reduced to 3,4-dihydro-4-phenyl-2-quinazolinone by NaBH4 in AcOH. In the experiment, the researchers used many compounds, for example, 2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5Electric Literature of 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 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.Electric Literature of C7H4Br2N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Ekiz, Makbule et al. published their research in Tetrahedron in 2016 | CAS: 68385-95-5

2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5) 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 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.Application of 68385-95-5

Convenient synthesis of disubstituted tacrine derivatives via electrophilic and copper induced reactions was written by Ekiz, Makbule;Tutar, Ahmet;Okten, Salih. And the article was included in Tetrahedron in 2016.Application of 68385-95-5 This article mentions the following:

The bromination of 2-aminobenzonitrile with mol. bromine (2 equiv) furnished 2-amino-3,5-dibromobenzonitrile in 98% yield. One-pot syntheses are described for dibromotacrine derivatives, e.g., I (Y = CH2), utilizing Friedlander reactions. A convenient route is described for disubstituted derivatives of tacrines from dibromotacrine I (Y = CH2, CH2CH2) (II) by various substitution reactions. Several disubstituted tacrines were synthesized by treatment of II with n-BuLi followed by trapping with an electrophile [Si(Me)3Cl, S2(Me)2]. Both were converted to the corresponding cyano derivatives III (X = Br, Y = CH2; X = CN, Y = CH2; X = CN, CH2CH2) via copper-assisted nucleophilic substitution reactions in moderate yields (30%, 50%, and 60%, resp.). Copper-induced nucleophilic substitution of dibromide II (Y = CH2CH2) with NaOMe afforded mono-methoxide IV in 25% yield. In the experiment, the researchers used many compounds, for example, 2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5Application of 68385-95-5).

2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5) 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 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.Application of 68385-95-5

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Yu, Boxuan et al. published their research in Nano Research in 2021 | CAS: 68385-95-5

2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5) 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. Formula: C7H4Br2N2

De novo synthesis of bifunctional conjugated microporous polymers for synergistic coordination mediated uranium entrapment was written by Yu, Boxuan;Zhang, Lei;Ye, Gang;Liu, Qingzhi;Li, Jiongli;Wang, Xudong;Chen, Jing;Xu, Shengming;Ma, Shengqian. And the article was included in Nano Research in 2021.Formula: C7H4Br2N2 This article mentions the following:

This work reports a de novo synthesis of novel bifunctional conjugated microporous polymers (CMPs) exhibiting a synergistic-effect involved coordination behavior to uranium. It is highlighted that the synthetic strategy enables the engineering of the coordination environment within amidoxime functionalized CMP frameworks by specifically introducing ortho-substituted amino functionalities, enhancing the affinity to uranyl ions via forming synergistic complexes. The CMPs exhibit high Brunauer-Emmett-Teller (BET) surface area, well-developed three-dimensional (3D) networks with hierarchical porosity, and favorable chem. and thermal stability because of the covalently cross-linked structure. Compared with the amino-free counterparts, the adsorption capacity of bifunctional CMPs was increased by almost 70%, from 105 to 174 mg/g, indicating evidently enhanced binding ability to uranium. Moreover, new insights into coordination mechanism were obtained by in-depth XPS anal. and d. functional theory (DFT) calculation, suggesting a dominant role of the oxime ligands forming a 1:1 metal ions/ligands (M/L) coordination model with uranyl ions while demonstrating the synergistic engagement of the amino functionalities via direct binding to uranium center and hydrogen-bonding involved secondary-sphere interaction. This work sheds light on the underlying principles of ortho-substituted functionalities directed synergistic effect to promote the coordination of amidoxime with uranyl ions. And the synthetic strategy established here would enable the task-specific development of more novel CMP-based functional materials for broadened applications. In the experiment, the researchers used many compounds, for example, 2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5Formula: C7H4Br2N2).

2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5) 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. Formula: C7H4Br2N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

29-Sep-2021 News Continuously updated synthesis method about 68385-95-5

The synthetic route of 68385-95-5 has been constantly updated, and we look forward to future research findings.

Synthetic Route of 68385-95-5, These common heterocyclic compound, 68385-95-5, name is 2-Amino-3,5-dibromobenzonitrile, its 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.

Bromine (110 mmol, 5.6 mL) was added dropwise to an acetic acid solution (150 mL) of 2-aminobenzonitrile (50 mmol, 5.9 g) in an argon atmosphere, and the mixture was stirred at room temperature for 5 hours. The reaction solution was poured into ice water (200 mL), and the resulting solid was collected by filtration and washed with water.The residue was recrystallized from ethyl acetate to obtain 2-amino-3,5-dibromobenzonitrile (6.9 g, yield 50%).The obtained 2-amino-3,5-dibromobenzonitrile (10.0 mmol, 2.75 g), tetrabutylammonium fluoride trihydrate (5.0 mmol, 1.58 g), trimethylsilyl azide (TMSN3) (15 0.0 mmol, 2.0 mL) was stirred at 85 C. for 2 hours under an argon atmosphere. Ethyl acetate was added to the reaction solution, and the mixture was extracted 3 times with 1M hydrochloric acid (5 mL), and then the organic layer was dried over magnesium sulfate and dried under reduced pressure.Ethyl acetate was distilled off. The residue was subjected to silica gel column chromatography (ethyl acetate: ethanol = 10: 1), and 2,4-dibromo-6- (1H-tetrazol-5-yl) aniline (1.40 g, yield 44%) was white. Obtained as a solid.

The synthetic route of 68385-95-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tohoku University; Uozumi, Nobuyuki; Arisawa, Mieko; Suzuki, Futoshi; Endo, Akira; Hamamoto, Susumu; Ikenokami, Yoshiaki; (20 pag.)JP2019/137678; (2019); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 68385-95-5

The synthetic route of 68385-95-5 has been constantly updated, and we look forward to future research findings.

68385-95-5, name is 2-Amino-3,5-dibromobenzonitrile, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. category: nitriles-buliding-blocks

To a solution of 2,4-dibromo-6-cyanoaniline (200.00 g, 724.82 mmol) and DMAP(17.71 g, 144.96 mmol) in DCM (3 L), Boc2O (474.58 g, 2.17 mol) was added and thereaction mixture was stirred at 45 C for 4 h. The crude mixture was successively washed with saturated NaHCO3 (2 x 1 L) and brine (2 x 1 L), dried over MgSO4, filtered and concentrated under vacuum to give 323 g of intermediate 1 (56% yield, yellow solid, 86% purity evaluated by LC/MS). The product was used in the next stepwithout any further purification.

The synthetic route of 68385-95-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; STANSFIELD, Ian; QUEROLLE, Olivier Alexis Georges; PONCELET, Virginie Sophie; GROSS, Gerhard Max; JACOBY, Edgar; MEERPOEL, Lieven; KULAGOWSKI, Janusz Jozef; MACLEOD, Calum; MANN, Samuel Edward; GREEN, Simon Richard; HYND, George; (477 pag.)WO2017/125530; (2017); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Continuously updated synthesis method about 2-Amino-3,5-dibromobenzonitrile

The synthetic route of 68385-95-5 has been constantly updated, and we look forward to future research findings.

Reference of 68385-95-5, These common heterocyclic compound, 68385-95-5, name is 2-Amino-3,5-dibromobenzonitrile, its 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.

Bromine (110 mmol, 5.6 mL) was added dropwise to an acetic acid solution (150 mL) of 2-aminobenzonitrile (50 mmol, 5.9 g) in an argon atmosphere, and the mixture was stirred at room temperature for 5 hours. The reaction solution was poured into ice water (200 mL), and the resulting solid was collected by filtration and washed with water.The residue was recrystallized from ethyl acetate to obtain 2-amino-3,5-dibromobenzonitrile (6.9 g, yield 50%).The obtained 2-amino-3,5-dibromobenzonitrile (10.0 mmol, 2.75 g), tetrabutylammonium fluoride trihydrate (5.0 mmol, 1.58 g), trimethylsilyl azide (TMSN3) (15 0.0 mmol, 2.0 mL) was stirred at 85 C. for 2 hours under an argon atmosphere. Ethyl acetate was added to the reaction solution, and the mixture was extracted 3 times with 1M hydrochloric acid (5 mL), and then the organic layer was dried over magnesium sulfate and dried under reduced pressure.Ethyl acetate was distilled off. The residue was subjected to silica gel column chromatography (ethyl acetate: ethanol = 10: 1), and 2,4-dibromo-6- (1H-tetrazol-5-yl) aniline (1.40 g, yield 44%) was white. Obtained as a solid.

The synthetic route of 68385-95-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tohoku University; Uozumi, Nobuyuki; Arisawa, Mieko; Suzuki, Futoshi; Endo, Akira; Hamamoto, Susumu; Ikenokami, Yoshiaki; (20 pag.)JP2019/137678; (2019); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Analyzing the synthesis route of 2-Amino-3,5-dibromobenzonitrile

According to the analysis of related databases, 68385-95-5, the application of this compound in the production field has become more and more popular.

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. 68385-95-5, name is 2-Amino-3,5-dibromobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 2-Amino-3,5-dibromobenzonitrile

General procedure: 4.3.1. General procedure for tacrine analogs. To a mixture of 2-amino-3,5-dibromobenzonitrile (1.0 mmol) and ketone (1.10 mmol) in toluene (12 mL) placed in a round bottom flask connected to a reflux condenser was added Lewis acid (1.20 mmol). The mixture was heated at 120 C for 24 h under stirring. After cooling to room temperature, the remaining solids were treated with NaOH solution (2 mol L-1, 12 mL) and this mixture was heated at reflux for 24 h. On cooling to room temperature, the reaction mixture was extracted with CHCl3 (3*25 mL), and the organic layers were combined and dried over Na2SO4. The solvent was evaporated under reduced pressure to give the desired product. The procedures were performed under an argon atmosphere in the presence of ZnCl2, InCl3, FeCl3, and BiCl3. The isolated products appeared to be sufficiently clean and no further purification was conducted.

According to the analysis of related databases, 68385-95-5, the application of this compound in the production field has become more and more popular.