Category: 16588-02-6

Some common heterocyclic compound, 16588-02-6, name is 2-Chloro-5-nitrobenzonitrile, molecular formula is C7H3ClN2O2, 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. Recommanded Product: 16588-02-6

General procedure: To solution of 1.97 mmol (1.2 eq.) of phenol 2-8, 12-13 in 3 ml dry DMSO was added 79 mg(1.2 eq.) powdered NaOH. The mixture was heated at 50C for 20 min and to the formed clearsolution 0.300 g (1.64 mmol, 1.0 eq.) of 1 was added. The reaction mixture was heated at 80C for 8h. After cooling 40 ml water was added and extracted with DCM. The organic phase was washedwith aq. NaHCO3 and water, dried over Na2SO4, filtered and evaporated in vacuo. The crudeproducts 14-20, 24-25 were purified by column chromatography (50 g silica-gel). After column theformed solid products were powdered, washed with 3 ml hot hexane and dried in vacuo.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 16588-02-6, its application will become more common.

Reference:
Article; Dobrikov, Georgi M.; Slavchev, Ivaylo; Nikolova, Ivanka; Stoyanova, Adelina; Nikolova, Nadya; Mukova, Lucia; Nikolova, Rosica; Shivachev, Boris; Galabov, Angel S.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 19; (2017); p. 4540 – 4543;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 16588-02-6 as follows. Formula: C7H3ClN2O2

2-(Benzylthio)-5-nitrobenzonitrile[0294] To a solution of 2-chloro-5-nitrobenzonitrile (27.375 g, 0.15 mol) in MeCN (500 ml) was added K2C03 (24.84 g, 0.18 mol) and phenylmethanethiol (17.71 ml, 0.15 mol). The solution was stirred at room temperature for overnight. The mixture was filtered through the celite pad and the filtrate was concentrated in vacuo to give 2-(benzylthio)-5-nitrobenzonitrile (40.5 g, 100%) as a yellow solid. 1H NMR: CDC13400 MHz 58.43 (s, 1H), 8.27-8.25 (m, 1H), 7.44-7.31 (m, 6H), 4.35 (s, 2H).

According to the analysis of related databases, 16588-02-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ANACOR PHARMACEUTICALS, INC.; HERNANDEZ, Vincent, S.; LI, Xianfeng; ZHANG, Suoming; AKAMA, Tsutomu; ZHANG, Yanchen; LIU, Yang; PLATTNER, Jacob, J.; ALLEY, Michael, Kevin Richard; ZHOU, Yasheen; NEIMAN, James, A.; WO2011/60196; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 16588-02-6, 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. 16588-02-6, name is 2-Chloro-5-nitrobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 2-chloro-5-nitrobenzonitrile (1 g, 5.49 mmol) and 3,5- difluorobenzenethiol (960 mg, 6.6 mmol) in DIVIF (20 mL) was added K2C03 (2.3 g, 16 mmol). The reaction was stirred at 80 C overnight. The residue was poured into H20 (20 mL) and the aqueous phase was extracted with EA (30 mL x2). The organic layer was washed with brine (20 mL), dried over Na2SO4 and concentrated. The residue was purified by silica gel column (PE/EA = 10/1) to give 2-((3,5-difluorophenyl)thio)-5-nitrobenzonitrile (620 mg, yield: 39%) as a yellow solid.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-Chloro-5-nitrobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INSTITUTE; GARDELL, Stephen; PINKERTON, Anthony B.; SERGIENKO, Eduard; SESSIONS, Hampton; (428 pag.)WO2018/132372; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 16588-02-6, name is 2-Chloro-5-nitrobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 2-Chloro-5-nitrobenzonitrile

3-Cyano-4-chloroaniline 2-Chloro-5-nitrobenzonitrile (25 g, 137 mmol) was dissolved in ethanol (275 mL). Stannous chloride dihydrate (154.5 g, 0.685 M) was added and the mixture stirred at 70 C. for 30 min. The mixture was then cooled to room temperature and poured into crushed ice. The mixture was made basic with solid sodium hydroxide. This mixture was extracted with ethyl acetate (3*100 mL). The extracts were combined, washed with brine, dried (MgSO4), concentrated and the residue dried under vacuum and recrystallized from ethanol to yield light brown needles (10.6 g, 51%).

The synthetic route of 16588-02-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chapdelaine, Marc; Davenport, Timothy; Haeberlein, Markus; Horchler, Carey; McCauley, John; Pierson, Edward; Sohn, Daniel; US2004/110745; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 16588-02-6, A common heterocyclic compound, 16588-02-6, name is 2-Chloro-5-nitrobenzonitrile, molecular formula is C7H3ClN2O2, 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.

4-chloro-3-cyanonitrobenzene (600 mg, 1 eq, 3.29 mmol) and DMF (5 mL) were added sequentially to a 100 mL round bottom flask , the flask was sealed with a rubber stopper and stirred the reaction under ice-water bath. Vacuum pumping then recharging N2 , repeat the cycle for 3 times and after stirring the reaction for 10min, the DMF solution of sodium methoxide was slowly injected into the sealed reaction flask through the syringe. After 1h of reaction, the reaction was completed and was stopped. After adding 100 mL of ethyl acetate for dilution, it was washed oncewith the saturated ammonium chloride aqueous solution and saturated aqueous sodium chloride solution. The aqueous phase was again washed with ethyl acetate and the combined organic phase was dried over anhydrous sodium sulfate for 30 min. The mixture was filtered , concentrated then separated by Silica gel column chromatography (PE : EA =5:1) to give a product of 440 mg of product as a White crystalline solid (compound 6) in 75% yield .

The synthetic route of 16588-02-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Long Yaqiu; Xu Zhongliang; Wang Heyao; Cai Mengxin; (31 pag.)CN106892871; (2017); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 16588-02-6, 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. 16588-02-6 name is 2-Chloro-5-nitrobenzonitrile, 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.

Reference Example 1 1-(2,6-Dichlorophenyl)-2-oxo-3,4-dihydro-6-(4-fluorophenyl)thioquinazolinea) 2-(2,6-dichlorophenylamino)-5-nitrobenzonitrile 2,6-Dichloroaniline (2.84 g, 17.5 mmol) was dissolved in DMSO (5 mL) and 60% NaH (0.60 g, 15 mmol) was added. The mixture was stirred 30 min and then 2-chloro-5-nitrobenzonitrile (0.91 g, 5.0 mmol) in DMSO (5 mL) was added. The reaction darkened and warmed to 50. After cooling to 23 the reaction was diluted with EtOAc (200 mL) and washed with H2O (3X), satd. aq. NaCl, and dried (Na2SO4), and concentrated to afford 1.45 g (94%) of the title compound as an ivory colored powder. 1H NMR (400) MHz, delta: 8.49 (finely split doublet, 1), 8.20 (dd, 1), 7.51 (d,2), 7.34 (d, 2), 6.41 (d,1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-5-nitrobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; SmithKline Beecham Corporation; EP1233951; (2005); B1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 16588-02-6, name is 2-Chloro-5-nitrobenzonitrile, 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 16588-02-6, Recommanded Product: 16588-02-6

A mixture of 3 -methyl- IH-1, 2;4-triazole (6.83 g, 82 mmol), 2- chloro-5-mtrobenzomtrile (15 g, 82 mmol), and potassium carbonate (34.1 g, 246 mmol) in anhydrous acetonitrile (200 mL) was heated at 70 0C for 16 h. The dark brown reaction mixture was allowed to cool to rt and was poured into water (500 mL). The aqueous mixture was extracted with EtOAc (3 x 200 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude residue was purified using silica gel chromatography (40-100% ethyl acetate/hexane, linear gradient) to afford 2-(3-methyl~lH-l,2,4-triazol-l-yl)-5- nitrobenzonitrile (10.9 g, 58 % yield). LC-MS (M+H)+ – 230.1. 1H NMR (500 MHz, chloroform-D) delta ppm 2.53 (s, 3 H) 8.10 (d, J-9.16 Hz, 1 H) 8.56 (dd, J-9.16, 2.44 Hz, 1 H) 8.68 (d, J-2.44 Hz, 1 H) 8.93 (s, 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-5-nitrobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MARCIN, Lawrence, R.; THOMPSON, Lorin, A., III; BOY, Kenneth, M.; GUERNON, Jason, M.; HIGGINS, Mendi, A.; SHI, Jianliang; WU, Yong-Jin; ZHANG, Yunhui; MACOR, John, E.; WO2010/83141; (2010); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 16588-02-6, 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. 16588-02-6 name is 2-Chloro-5-nitrobenzonitrile, 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: To solution of 1.97 mmol (1.2 eq.) of phenol 2-8, 12-13 in 3 ml dry DMSO was added 79 mg(1.2 eq.) powdered NaOH. The mixture was heated at 50C for 20 min and to the formed clearsolution 0.300 g (1.64 mmol, 1.0 eq.) of 1 was added. The reaction mixture was heated at 80C for 8h. After cooling 40 ml water was added and extracted with DCM. The organic phase was washedwith aq. NaHCO3 and water, dried over Na2SO4, filtered and evaporated in vacuo. The crudeproducts 14-20, 24-25 were purified by column chromatography (50 g silica-gel). After column theformed solid products were powdered, washed with 3 ml hot hexane and dried in vacuo.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-5-nitrobenzonitrile, and friends who are interested can also refer to it.

Reference:
Article; Dobrikov, Georgi M.; Slavchev, Ivaylo; Nikolova, Ivanka; Stoyanova, Adelina; Nikolova, Nadya; Mukova, Lucia; Nikolova, Rosica; Shivachev, Boris; Galabov, Angel S.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 19; (2017); p. 4540 – 4543;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 16588-02-6, name is 2-Chloro-5-nitrobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 2-Chloro-5-nitrobenzonitrile

2-Chloro-5-nitrobenzonitrile (0.91 g, 5.0 mmol) was added to the reaction flask.Ethyl piperazine-1-carboxylate (0.84 g, 5.3 mmol),Triethylamine (1.1 g, 10.9 mmol) and acetonitrile 20 mL were refluxed for 4.5 h.After the reaction, the reaction solution was cooled to room temperature, diluted with water and extracted with ethyl acetate.The organic layer was dried over anhydrous sodium sulfate, filtered and evaporated.The residue was recrystallized from ethyl acetate to give 1a, yield 71.7%

The synthetic route of 16588-02-6 has been constantly updated, and we look forward to future research findings.

Related Products of 16588-02-6, 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. 16588-02-6 name is 2-Chloro-5-nitrobenzonitrile, 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 typical experiment, p-CNB (1 g, 6.35 mmol), CuI (0.635 mmol),commercial 25% aqueous NH3 solution (10 mL, NH3/p-CNB molar ratio21/1) were loaded into a 50 mL stainless steel reactor and sealed. Thematerial of the autoclave used is AISI 316 L, for which the compositionis Cr 16-18%, Ni 10-14%, Mo 2-3%, MnQ2%, Si Q1%, CQ0.03%,SQ0.03%, PQ0.045%, and the other part is Fe. After being heated to200 C, the reaction was conducted while stirring with a magneticstirrer (1200 rpm). The pressure of the vapor phase (NH3 and H2O) wasabout 3 MPa at the reaction temperature. After stirring for 1 h, the reactorwas cooled to room temperature and the reaction mixture wasseparated by centrifugation. The solid substrate and product were dissolvedin ethanol and analyzed by a gas chromatograph (Shimadzu GC-2010) equipped with a capillary column (Rtx-5 capillary column: 30m¡Á0.25mm ¡Á0.25 Tm, carrier: N2) and a flame ionization detector(FID) and gas chromatograph-mass spectrometer (GC-MS, Agilent 5890,HP-5). o-Xylene was used as an internal standard for quantitativeanalysis. The liquid phase was also analyzed by gas chromatograph andno p-CNB or p-NAN were detected. The carbon balance was near 99%and trace amount of other unidentified byproducts were observed.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-5-nitrobenzonitrile, and friends who are interested can also refer to it.

Reference:
Article; Li, Yan; Shi, Ruhui; Lin, Weiwei; Cheng, Haiyang; Zhang, Chao; Arai, Masahiko; Zhao, Fengyu; Molecular catalysis; vol. 475; (2019);,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts