Category: 53312-82-6

Related Products of 53312-82-6, A common heterocyclic compound, 53312-82-6, name is 4-Amino-2-bromobenzonitrile, molecular formula is C7H5BrN2, 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.

To a stirred mixture of 4-amino-2-bromobenzonitrile (2.00 g, 10.2 mmol), cyclopropyl boronic acid (1,18 g, 13.7 mmol) and K3PO4 (3.23 g, 15.2 mmol) in the mixed solvents of EtOH/H2O/toluene (2 mL/2 mL/12 mL) under nitrogen was added PdCl2(PPh3)2 (0.72 g, 1.03 mmol). This mixture was heated at 800C for 19 h and cooled to room temperature. Next, the mixture was diluted with 150 mL of EtOAc and filtered through a pad of silica gel topped with a layer of celite. This pad was further rinsed with EtOAc (2 x 100 mL). The filtrate was washed with 25 mL of brine, dried over MgSO4, filtered and concentrated in vacuo to give the crude amine. The crude amine was purified by an ISCO auto flash chromatographer using 12O g silica gel column, eluted with hexanes/CH2Cl2 solvents in a 25 min 50% to 100% gradient elution to give 0.75 g of Preparation 4OA as a white solid in 47% yield. [00428] HPLC: 1.55 min (RT) (Chromolith SpeedROD column 4.6 x 50 mm, 10- 90% aqueous MeOH over 4 minutes containing 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nm). MS (ES): m/z=159 [M+H]+. 1H NMR of 4-amino-2- cyclopropyl-benzonitrile (400 MHz, CDCl3) delta ppm 7.34 (d, J=8.31 Hz, 1 H) 6.44 (dd, J=8.31, 2.27 Hz, 1 H) 6.12 (d, J=2.01 Hz, 1 H) 4.01 (s, 2 H) 2.13-2.24 (m, 1 H) 1.02- 1.12 (m, 2 H) 0.68-0.76 (m, 2 H).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2009/3077; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 53312-82-6, name is 4-Amino-2-bromobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Formula: C7H5BrN2

40 mg CuCI were dissolved in 10 m I water and cooled in an ice bath to 00C. 1.6 ml thionylchloride were added dropwise. The reaction solution was allowed to warm to roomtemperature overnight.1.O g 4-Amino-2-bromo-benzonitrile were suspended in 12 ml hydrochlorc acid and 45 ml water and warmed to 960C until all 4-Amino-2-bromo-benzonitrile were dissolved. The solution was cooled to -5C and 380 mg NaNO2 dissolved in 10 ml water were added. Then the thionlychloride solution was cooled to -2C and added dropwise. The 3-Bromo-4-cyano-benzenesulfonyl chloride precipitated and was collected by filtration and washed with ice cooled water and dried under vacuo to obtain 956 mg 3-Bromo-4- cyano-benzenesulfonyl chloride as a solid. This material was used without further purification. C7H3BrCINO2S (280.53).

According to the analysis of related databases, 53312-82-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SANOFI-AVENTIS; WO2009/149820; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 53312-82-6, name is 4-Amino-2-bromobenzonitrile, 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 53312-82-6, Product Details of 53312-82-6

To a 40 mL vial with a stir bar are added 4-amino-2-bromobenzonitrile (637 mg, 3.23 mmol), maleic anhydride (317 mg, 3.23 mmol), and cyclohexanone (1.70 mL, 16.2 mmol). The reaction is heated to 150 C. for 16 hours then cooled to room temperature. The product is purified by gradient flash chromatography eluding with 0% to 10% MeOH in CH2Cl2 to provide [1-(3-bromo-4-cyanophenyl)-2-oxo-2,4,5,6,7,7a-hexahydro-1H-indol-3-yl]-acetic acid as a tan solid (456 mg, 38% yield) (LC/MS m/z=375 [M+H]+).

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Reference:
Patent; Huang, Kenneth He; Hughes, Philip; Ma, Wei; Ommen, Andy; Woodward, Angela; Veal, James; Barta, Thomas; US2008/76813; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 53312-82-6, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 53312-82-6, name is 4-Amino-2-bromobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 4-amino-2-bromobenzonitrile (440 mg, 2.2 mmol), ferf-butyl 2-oxo-6azaspiro[3.4]octane-6-carboxylate (495 mg, 2.2 mmol) and decaborane (43 mg, 0.35 mmol) in MeOH (20 mL) was stirred at 50 C overnight under Ar. The reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Petroleum ether/EtOAc = 3/1) to afford intermediate 39 (406 mg, 45% yield) as a white solid.

The synthetic route of 4-Amino-2-bromobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; JOHNSON & JOHNSON (CHINA) INVESTMENT LTD.; DAI, Xuedong; QUEROLLE, Olivier Alexis Georges; KROSKY, Daniel Jason; CAI, Wei; FU, Liqiang; KONG, Linglong; LIU, Yingtao; WAN, Zhao-Kui; HERKERT, Barbara; PANDE, Vineet; EDWARDS, James Patrick; PATRICK, Aaron Nathaniel; ANGIBAUD, Patrick Rene; PONCELET, Virginie Sophie; (488 pag.)WO2019/120209; (2019); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 53312-82-6, A common heterocyclic compound, 53312-82-6, name is 4-Amino-2-bromobenzonitrile, molecular formula is C7H5BrN2, 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.

To a stirred mixture of 4-amino-2-bromobenzonitrile (2.00 g, 10.2 mmol), cyclopropyl boronic acid (1,18 g, 13.7 mmol) and K3PO4 (3.23 g, 15.2 mmol) in the mixed solvents of EtOH/H2O/toluene (2 mL/2 mL/12 mL) under nitrogen was added PdCl2(PPh3)2 (0.72 g, 1.03 mmol). This mixture was heated at 800C for 19 h and cooled to room temperature. Next, the mixture was diluted with 150 mL of EtOAc and filtered through a pad of silica gel topped with a layer of celite. This pad was further rinsed with EtOAc (2 x 100 mL). The filtrate was washed with 25 mL of brine, dried over MgSO4, filtered and concentrated in vacuo to give the crude amine. The crude amine was purified by an ISCO auto flash chromatographer using 12O g silica gel column, eluted with hexanes/CH2Cl2 solvents in a 25 min 50% to 100% gradient elution to give 0.75 g of Preparation 4OA as a white solid in 47% yield. [00428] HPLC: 1.55 min (RT) (Chromolith SpeedROD column 4.6 x 50 mm, 10- 90% aqueous MeOH over 4 minutes containing 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nm). MS (ES): m/z=159 [M+H]+. 1H NMR of 4-amino-2- cyclopropyl-benzonitrile (400 MHz, CDCl3) delta ppm 7.34 (d, J=8.31 Hz, 1 H) 6.44 (dd, J=8.31, 2.27 Hz, 1 H) 6.12 (d, J=2.01 Hz, 1 H) 4.01 (s, 2 H) 2.13-2.24 (m, 1 H) 1.02- 1.12 (m, 2 H) 0.68-0.76 (m, 2 H).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2009/3077; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

These common heterocyclic compound, 53312-82-6, name is 4-Amino-2-bromobenzonitrile, 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. Computed Properties of C7H5BrN2

To a mixture of 4-amino-2-bromobenzonitrile (1.00 g, 5.08 mmol), 2-ethyl-5,7-dimethyl- 3-(4-(4,4,5,5-tetramethyl-1 ,2-dioxaborolan-2-yl)benzyl)-3H-imidazo[4,5-b]pyridine (OOld, 1.773 g, 4.53 mmol) and K2C03 (2.505 g, 18.13 mmol) was added 1,4-dioxane and 0 (2:1, 30 mL). The reaction mixture was then purged with a stream of N2 for 5 min in a sealable vial before Pd(Ph3P)4 (0.262 g, 0.227 mmol) was added. The reaction vial was sealed and the mixture heated at 100C for 18h. The cooled reaction mixture was then diluted with EtOAc (50 mL), washed with 0 and brine, dried (Na2S04) and evaporated. The crude residue was purified by flash chromatography (ISCO, 0-100% EtOAc-DCM) to afford the title compound (1.46 g, 4.53 mmol, 85%) as a white solid. LC-MS (Method H): 1.220 min, [M + H]+= 382.5; H NMR (400 MHz, CDC13) delta ppm 7.37 – 7.55 (m, 3H), 7.19 (d, / = 8.2 Hz, 2H), 6.90 (s, 1H), 6.51 – 6.68 (m, 2H), 5.51 (s, 2H), 4.17 (br s, 2H), 2.81 (d, / = 7.4 Hz, 2H), 2.59 (s, 3H), 2.64 (s, 3H), 1.33 (t, / = 7.4 Hz, 3H).

The synthetic route of 4-Amino-2-bromobenzonitrile has been constantly updated, and we look forward to future research findings.

Synthetic Route of 53312-82-6, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 53312-82-6, name is 4-Amino-2-bromobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

4-amino-2-bromobenzonitrile (0.055 g, 0.281 mmol) was stirred in dichloromethane (2 mL) and 0.50 mL saturated sodium bicarbonate solution (0.024 g, 0.281 mmol) solution at 0 C. Phosgene (20% in toluene, 0.3 mL, 0.561 mmol) was added and stirred for 30 min. The organic layer was extracted with dichloromethane and washed with water followed by sodium bicarbonate solution. The organic layer was concentrated and redissolved in DMF (2 mL). 5-(pyridin-4-yl)-1,3,4-thiadiazol-2-amine (0.050 g, 0.281 mmol) was added and heated at 90 C for 1 h. The resulting solid was filtered and washed with water, ethyl acetate and acetone to yield compound 24 as a pure solid (0.045 g, 0.112 mmol, 40%). See below for characterization data.

The synthetic route of 4-Amino-2-bromobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Rosenthal, Andrew S.; Dexheimer, Thomas S.; Gileadi, Opher; Nguyen, Giang H.; Chu, Wai Kit; Hickson, Ian D.; Jadhav, Ajit; Simeonov, Anton; Maloney, David J.; Bioorganic and Medicinal Chemistry Letters; vol. 23; 20; (2013); p. 5660 – 5666;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts