Tag: M.W=100-200

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. 123-06-8, name is Ethoxymethylenemalononitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: Ethoxymethylenemalononitrile

Triethylamine (9.7mL, 69.6mmol) was added to tert-butylhydrazine hydrochloride (8.67g, 69.6mmol) After adding absolute ethanol (460mL) and stirring at room temperature to dissolve, Ethoxymethylenemalononitrile (8.5 g, 69.6 mmol) was added in small portions, the solution was heated to reflux for 3 hours, and then the solvent was evaporated in vacuo to obtain a crude orange product. It was extracted with a mixed solution of ethyl acetate (0.5 L) and water (0.25 L), dried over anhydrous magnesium sulfate, and the organic layer was evaporated to obtain an orange solid. Continue to wash the obtained solid with a cyclohexane solution containing 10% ethyl acetate to obtain crystalline solid 5-amino-1-tert-butyl 1hydro-pyrazole-4-cyano 9.54g (yield 83% ).

According to the analysis of related databases, 123-06-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sichuan University Huaxi Hospital; Chengdu Huaxi Jingzhun Medical Industrial Technology Institute Co., Ltd.; He Yang; Li Weimin; Zhou Xinglong; Wu Qiong; Wu Xiaoai; Chen Hai; Huang Ridong; Chai Yingying; (17 pag.)CN110642861; (2020); A;,
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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. 610-66-2, name is 2-(2-Nitrophenyl)acetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 2-(2-Nitrophenyl)acetonitrile

Absolute ethanol (2,250 ml) and 1,500 g (9.25 moles) of o-nitrophenylacetonitrile is charged into a 22 liter flask. The suspension is cooled to 5-10 and hydrogen chloride is bubbled into the mixture for 2.5 hours. The reaction mixture is stirred at 10 under nitrogen atmosphere overnight. It is then diluted with 16,000 ml of ether and stirred for 1 hour; the solid is collected by filtration, washed with 4*1,000 ml of ether and dried (5 mm Hg/40) to give ethyl 2-(o-nitrophenyl)-acetimidate hydrochloride, m.p. 122-123 (dec).

The synthetic route of 610-66-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ciba-Geigy Corporation; US4595535; (1986); A;,
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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. 194853-86-6, name is 4-Fluoro-2-(trifluoromethyl)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 4-Fluoro-2-(trifluoromethyl)benzonitrile

. 4-({[2-(methyloxy)phenyI]methyl}amino)-2-(trifluoromethyl)benzonitriIeTo a solution of 4-flouro-2-(trifluouromethyl)benzonitrile (reagent A) (500 mg, 2.6 mmol) in anhydrous DMF (0.5 M) was added 2-methoxybenzylamine (reagent B) (0.35 mL, 2.6 mmol) and oven-dried potassium carbonate (365 mg, 2.6 mmol). The reaction mixture stirred at 85 0C for 18 hours. After cooling to room temperature, the reaction mixture was diluted with water. The organics were extracted into ethyl ether and dried over sodium sulfate. The Filtrate was concentrated, and remaining DMF was removed under reduced pressure to yield a beige solid (415 mg, 51% crude yield): MS (ESI) 306.3 (MH)+.

The synthetic route of 194853-86-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/113552; (2006); A2;,
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Related Products of 50397-74-5, 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 50397-74-5 as follows.

General procedure: Aniline 1 (0.5 mmol), H2O (5 mL), KOH (1 mmol, 2 equiv), and the CTAB (0.05 mmol, 10% mmol) were added to the reaction vessel stirring for 5 min. Allyl bromide (1 mmol, 2 equiv) was added, while maintaining the temperature at 80 C for 10 min under microwave irradiation (850 W). After completion of the reaction, the mixture was extracted with CH2Cl2 (3 × 15 mL). The combined organic layer was washed with brine (20 mL), dried over Na2SO4, and evaporated. The residue was purified by column chromatography (petroleum ether/ethyl acetate) to afford N-allylaniline 2a-j.

According to the analysis of related databases, 50397-74-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Liu, Meiyu; Wang, Xie; Sun, Xiaoliang; He, Wei; Tetrahedron Letters; vol. 55; 16; (2014); p. 2711 – 2714;,
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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;,
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Adding a certain compound to certain chemical reactions, such as: 134997-74-3, name is 3-Oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbonitrile, 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 134997-74-3, SDS of cas: 134997-74-3

To a stirred solution of 3-oxo-3,4-dihydro-2H-benzo[b][1 ,4]oxazine-6-carbonitrile (3.30 g, 1 9.0 mmol) in N,N-dimethylformamide (35 mL) was added sodium hydride (758 mg, 1 9 mmol, 60% dispersion in mineral oil) and iodoethane (3.84 g, 25 mmol, 1 .97 mL) at 0 C. The mixture was warmed to 20 00. After 3 h, the mixture was cooled to 0 C, quenched by addition of water (50 mL), and extracted with ethylacetate (60 mL x 4). The combined organic phases were washed with saturated aqueous sodium chloride solution (20 mL), dried over anhydrous sodium sulfate, filtered, and concentrated to give crude product that was purified by chromatography (silica, petroleum ether : ethyl acetate 50:1 to 5:1) to give 4-ethyl-3-oxo-3,4-dihydro-2H-benzo[b][1 ,4]oxazine-6-carbonitrile (1 .30 g, 6.43 mmol, 34 %) as a white solid. 1H NMR (400 MHz, CDC3) O 7.25 (dd, J 1.8, 8.3 Hz, 1 H), 7.17 (d, J 1 .8 Hz, 1 H), 6.98 (d, J8.3 Hz, 1H), 4.62 (s, 2H), 3.93 (q, J 7.2 Hz, 2H), 1.23 (t, J 7.2 Hz, 3H); LOMS (ESI) m/z 203.1 [M÷H]÷.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; YUMANITY THERAPEUTICS; LUCAS, Matthew; LE BOURDONNEC, Bertrand; WRONA, Iwona; PANDYA, Bhaumik; TIVITMAHAISOON, Parcharee; OZBOYA, Kerem; VINCENT, Benjamin; TARDIFF, Daniel; PIOTROWSKI, Jeff; SOLIS, Eric; SCANNEVIN, Robert; CHUNG, Chee-Yeun; ARON, Rebecca; RHODES, Kenneth; (489 pag.)WO2018/81167; (2018); A1;,
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Reference of 4421-09-4, 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. 4421-09-4, name is 3,4-(Methylenedioxy)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Synthesis of 5-substituted-1H-tetrazoles (general procedure): To a solution of aryliodide (1 mmol) in DMF (5 ml) was added sodium cyanide (1.2 mmol), catalyst(10 mol %) and the reaction mixture was stirred under heating at 100 C for appropriate time to obtain nitrile compound (see Table 1). To the nitrile compound generated in situ was added sodium azide (1.5 mmol) and the reaction was continued till the complete conversion of nitrile to tetrazole. After the completion of the reaction, the catalyst from the reaction mixture was easily separated out by centrifuging the reaction mixture. After the separation of the catalyst the crude material was then taken into ethyl acetate and washed with 5 N HCl and the layers separated. The organic layer was then washed with water, dried over anhyd sodium sulfate and concentrated to obtain the crude product. The crude product was purified by silica gel column chromatography using appropriate solvent mixtures to obtain the pure products (see Tables 1 and 2). Detailed experimental conditions and spectroscopic data were given insupplementary data.

The synthetic route of 3,4-(Methylenedioxy)benzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yapuri, Umanadh; Palle, Sadanandam; Gudaparthi, Omprakash; Narahari, Srinivasa Reddy; Rawat, Dhwajbahadur K.; Mukkanti, Khagga; Vantikommu, Jyothi; Tetrahedron Letters; vol. 54; 35; (2013); p. 4732 – 4734;,
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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, Application In Synthesis of 2-Chloro-5-nitrobenzonitrile

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;,
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Some common heterocyclic compound, 6393-40-4, name is 4-Amino-3-nitrobenzonitrile, molecular formula is C7H5N3O2, 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: 6393-40-4

3-Nitro-4-aminobenzonitrile (3.00 g) was dissolved in ethanol (300 ml) and added with stannous chloride dihydrate (20.7 g) and the whole was heated to 60C. Sodium borohydride (348 mg) was gradually added thereto and the whole was stirred overnight at 60C. After completion of the reaction, the resultant was added with water (300 ml) and neutralized with a 5 mol/l sodium hydroxide aqueous solution. After ethanol was distilled off under reduced pressure, the aqueous layer was added with ethyl acetate for extraction. The organic layer was washed with a saturated saline solution and then dried with anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure. The residue was recrystallized, thereby obtaining the subject compound (1.11 g) as a brown crystal. MS(EI):m/z=133[M]+ 1H-NMR(500MHz,CDCl3):delta=6.68(1H,d,J=8,1Hz),6.95(1H,s),7.05(1H,d,J=8.1Hz).3-Nitro-4-amino-benzonitrile (4.38 g) was dissolved in ethanol (600 ml) and added with stannous chloride dihydrate (34.6 g) and the whole was heated to 60C. Sodium borohydride (366 mg) was gradually added thereto and the whole was stirred overnight at 60C. After completion of the reaction, the resultant was filtrated through Celite and the filtrate was subjected to distillation of the solvent under reduced pressure. The residue was dissolved in chloroform, washed with a saturated aqueous sodium hydrogen carbonate solution and a saturated saline solution, and then dried with anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure. The residue was allowed to recrystallize (hexane/ethyl acetate), thereby obtaining the subject compound (2.56 g) as a brown crystal. MS (EI) :m/z=133[M]+ 1H-NMR(500MHz,CDCl3):delta=6.68(1H,d,J=8.1Hz),6.95(1H,s),7.05(1H, d,J=8.1Hz).An ethanol solution (300 ml) containing 4-amino-3-nitrobenzonitrile (3.00 g) was added with stannous chloride dihydrate (20.7 g) and then added with sodium borohydride (348 mg) . The whole was stirred overnight at 60C. After that, the resultant was subjected to distillation until the amount of the solution became about 100 ml. The resultant was added with water (100 ml) and a large amount of solid component was generated. The resultant was added with a 5 mol/l sodium hydroxide aqueous solution (42 ml) to adjust to pH 7. The solvent was distilled off. The solid component was filtrated out through Celite and washed with methanol and ethyl acetate in the stated order. The filtrate was again filtrated through Celite and only organic solvent was distilled off under reduced pressure. The remaining aqueous layer was subjected to extraction with ethyl acetate and dried with anhydrous magnesium sulfate , and the solvent was distilled off, thereby obtaining the subject compound (2.29 g) as a khaki crystal.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6393-40-4, its application will become more common.

Reference:
Patent; Kureha Corporation; EP1724263; (2006); A1;,
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Reference of 64248-63-1, The chemical industry reduces the impact on the environment during synthesis 64248-63-1, name is 3,5-Difluorobenzonitrile, I believe this compound will play a more active role in future production and life.

3-Fluoro-5-methoxybenzoic Acid In a 250 ml round bottom flask equipped with stir bar added 3,5-Difluorobenzonitrile (4.2 g, 30.4 mmol), sodium methoxide (10.4 ml, 45.6 mmol, 25% methanol) and dimethylformamide (40 ml). Stirred the resulting reaction mixture at room temperature, overnight. The reaction mixture was concentrated in-vacuo and residue was dissolved in dichloromethane (200 ml). The organic phase was washed sequentially with water (150 ml) and brine (150 ml), dried (sodium sulfate) and concentrated in-vacuo. The crude residue was purified on silica gel using 10% diethyl ether in hexanes to isolate 3-Fluoro-5-methoxybenzonitrile (1.63 g) as a white 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, 3,5-Difluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Wagenen, Bradford Van; Stormann, Thomas M.; Moe, Scott T.; Sheehan, Susan M.; McLeod, Donald A.; Smith, Daryl L.; Isaac, Methvin Benjamin; Slassi, Abdelmalik; US2003/55085; (2003); A1;,
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