Category: nitriles-buliding-blocks

31643-49-9, name is 4-Nitrophthalonitrile, 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. 31643-49-9

4-Nitrophthalonitrile or 3-nitrophthalonitrile and 2-propyn-1-ol were dissolved in 10.0mL dry DMSO and stirred at room temperature under nitrogen for 15min. Then anhydrous potassium carbonate (9.83mmol, 0.679g) was added. Dry ground potassium carbonate (2.85mmol, 0.399g) was further added after 3h and again after 24h. After 25h, water (100mL) was added to the reaction mixture. The brownish raw product was extracted with CHCl3, washed with pure water, dried with Na2SO4, and finally the solvent was removed under vacuum. Subsequently the crude product was purified by the column chromatography on silica gel using eluent CHCl3:MeOH (10:1). 2.2.1 Synthesis of 4-(prop-2-ynyloxy)-phthalonitrile (1) (0007) 4-Nitrophthalonitrile (5.78mmol, 1.07g) and 2-propyn-1-ol (6.94mmol, 0.38g) was used to get 1 as a pale-green solid. Yield: 0.921g (88%); m.p. 152-158C. FT-IR (ATR), numax/(cm-1): 3286 (-C?C-H), 3120, 3077 (C-Harom), 2997 (C-Halip), 2230 (C?N), 2135 (C?C), 1594, 1492 (C=Carom), 1256, 1086 (C-O-C). 1H NMR 250MHz (CDCl3) delta: 7.77 (dd, 1H, Harom), 7.38 (t, 1H, Harom), 7.30 (dd, 1H, Harom), 4.82 (d, 2H, -CH2), 2.63 (t, 1H, -C?CH). 13C NMR (CDCl3) delta: 160.41, 135.20, 120.10, 119.90, 117.51, 115.48, 115.12, 108.31, 77.80, 76.14, 56.57. Anal. Calc. for C11H6N2O: C, 72.52; H, 3.32; N, 15.38. Found: C, 72.45; H, 3.25; N, 15.29%. EI-MS (70eV): m/z Calc.: 182.05; Found: 181.07 [M-H]+.

Statistics shows that 31643-49-9 is playing an increasingly important role. we look forward to future research findings about 4-Nitrophthalonitrile.

Reference:
Article; Koyun, Oezge; Goerduek, Semih; Keskin, BahadIr; Cetinkaya, Ahmet; Koca, AtIf; Avciata, Ulvi; Polyhedron; vol. 113; (2016); p. 35 – 49;,
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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. 4360-47-8, name is Cinnamonitrile, This compound has unique chemical properties. The synthetic route is as follows., 4360-47-8

General procedure: Nitro compound or olefin(5 mmol) and hydrogen source (25 mmol) were dissolved inMeOH (10 mL, 0.5 M). After flushing the column with MeOH,the substrate/reagent solution was pumped through the columnat the specified temperature with a flow rate of 0.108 mL/minby using Vapourtec E-series equipment (with a peristalticpump). Alternatively, a syringe pump can be used. The firstcolumn volume was discarded, the second was collected. Thesolvent was evaporated, the residue added to distilled water (20 mL), and extracted with diethyl ether or dichloromethane(3 ¡Á 15 mL). The combined organic phases were dried overMgSO4, filtered, and the solvent was removed in vacuo.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Hutchings, Matthew; Wirth, Thomas; Synlett; vol. 27; 12; (2016); p. 1832 – 1835;,
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876-31-3, 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. 876-31-3, name is 4-(Cyanomethyl)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A solution of 10 (4 mmol, 1 equiv.), appropriate 4-cyanophenylacetonitrile (5.24 mmol, 1.3 equiv.),and anhydrous DMF (10 mL) was stirred for 0.5 h at 15 C under N2. Then, NaH (13.71 mmol; 60%dispersion in mineral oil, 2 equiv.) was added portion-wise at 15 C. Then, the mixture was stirredat 15 C for another 2 h, warmed to room temperature, and then reacted for 48-72 h (monitored byTLC). The resulting mixture was poured into a saturated ammonium chloride solution. The precipitatewas collected by filtration and the residue was then purified via column chromatography on silica gel,eluting with EtOAc/petroleum ether (1:3) to obtain compounds A1-A12 and B1-B6 as white or yellowsolids. Full characterization data for all final compounds can be found in the Supporting Information. 4-(4-(cyano-(4-cyanophenyl)methyl)-pyrimidin-2-ylamino)benzonitrile (A1) Yield = 87%. mp:243.2-244.7 C. 1H NMR (400 MHz, THF-d8) 9.39 (s, NH), 8.40 (d, J = 5.0 Hz, 1H), 7.80 (d, J = 8.7 Hz,2H), 7.68 (d, J = 8.2 Hz, 2H), 7.58 (d, J = 8.2 Hz, 2H), 7.48 (d, J = 8.7 Hz, 2H), 6.86 (d, J = 5.0 Hz, 1H), 5.53(s, 1H). 13C NMR (101 MHz, THF-d8) 163.6, 159.6, 159.3, 143.8, 139.0, 132.4 (2C), 132.2 (2C), 128.6 (2C),120.3, 118.2 (2C), 117.1, 116.8, 112.5, 110.4, 104.3, 43.5. HRMS (ESI): m/z calcd for C20H12N6 [M H]+335.1051, found 335.1053.

The synthetic route of 876-31-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chen, Fen-Er; Li, Ting-Ting; Pannecouque, Christophe; Zhuang, Chun-Lin; de Clercq, Erik; Molecules; vol. 25; 7; (2020);,
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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. 64113-84-4 name is 2-Fluoro-5-methylbenzonitrile, 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. 64113-84-4

Combine 4-fluoro-2-nitro-phenylamine (2.9g, 18.50 mmol), 2-fluoro-5-methyl- benzonitrile (2. 5g, 18.50 mmol) and lithium hydroxide monohydrate (2.4g, 57.20 mmol) in methyl sulfoxide (DMSO, 40 ml). Heat the resulting mixture to 55 [C] for 40 hours. Cool the reaction mixture to ambient temperature, then pour into approximately 250 ml of ice water and stir for one hour. Filter the resulting mixture and collect the precipitate. Chromatograph the solid using flash chromatography and elute with mobile phase: 90% hexanes, 5% ethyl acetate, and 5% dichloromethane to obtain 2.267g of the title compound (8.36 mmol, 45% yield) as an orange amorphous solid: Mass Spectrum [(M/E)] : 272 (M+1).

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

Reference:
Patent; ELI LILLY AND COMPANY; WO2004/14895; (2004); A1;,
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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. 403-54-3 name is 3-Fluorobenzonitrile, 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. 403-54-3

(a) 3-Cyano-4-nitrofluorobenzene m-Fluorobenzonitrile (96.8 g., 0.8 mol) is added in two and one-half hours to a mixture of concentrated sulfuric acid (600 ml.) and potassium nitrate (80.9 g., 0.8 mole) at 3-6 C., then allowed to warm to 25 C. The mixture is poured over cracked ice (3000 ml.), extracted with chloroform (5*250 ml.), dried and the solvent removed. The residue is extracted with pentane and dried to give 3-cyano-4-nitrofluorobenzene (115 g., 86.5%) m.p. 102-104 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Fluorobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Rohm and Haas Company; US4330324; (1982); A;,
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127946-77-4, 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. 127946-77-4, name is 1-Amino-1-cyclopropanecarbonitrile hydrochloride belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

1-azanylcyclopropane-1-carbonitrile hydrochloride (671.53 mg, 5.66 mmol), (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(3-pyridyl)propanoic acid (2 g, 5.15 mmol) and HATU (2.15 g, 5.66 mmol) were suspended in DMF (15 mL). DIPEA (2.63 mL, 15.45 mmol) was added and mixture stirred for 16H at room temperature. The mixture was diluted with EtOAc and washed with water and brine. Organic layer was separated, dried (Na2SO4), filtered and concentrated to get a crude which was purified by column chromatography. Biotage SNAP KP-SiO2 100 g; eluent: solvent A: petroleum ether; solvent B: EtOAc.

The synthetic route of 1-Amino-1-cyclopropanecarbonitrile hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nizi, Emanuela; Sferrazza, Alessio; Fabbrini, Danilo; Nardi, Valentina; Andreini, Matteo; Graziani, Rita; Gennari, Nadia; Bresciani, Alberto; Paonessa, Giacomo; Harper, Steven; Bioorganic and Medicinal Chemistry Letters; vol. 28; 9; (2018); p. 1540 – 1544;,
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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 40497-11-8 as follows. 40497-11-8

In a 250 mL round-bottomed three-necked flask, 0.01 mol of 3-methylaniline and a small amount of ethanol were added,3.0 mL (0.035 mol) of concentrated hydrochloric acid was added dropwise under ice-cooling with stirring.0.018 mol of sodium nitrite was dissolved in 10 mL of water,Slowly dropping into the flask,After the reaction was completed 0.5h yellow diazonium salt solution.0.01 mol of ethyl 2,3-dicyanopropionate was added to a three-necked flask,The prepared diazonium salt solution was dropped into the flask,After dropping the reaction 2 h.Adding ammonia,Adjust the pH to 9-10,Reaction at room temperature for 2h.After completion of the reaction, the reaction mixture was extracted with 40 mL of dichloromethane,The organic layer was washed with water (2 x 30 mL)Washed with saturated sodium chloride solution (1 x 40 mL)Dried over anhydrous magnesium sulfate,Partial distillation of the solvent under reduced pressure gave 1.50 g of product,Yield 76.2%

According to the analysis of related databases, 40497-11-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Nanjing University of Technology; Wan, Rong; Wu, Shaohua; Guo, Chunwei; Wang, Xinlin; Chen, Fuli; Han, Zhenyu; Fu, Xiaohuan; (13 pag.)CN105820167; (2016); A;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 6136-68-1, name is 3-Acetylbenzonitrile, A new synthetic method of this compound is introduced below., 6136-68-1

Example 15; Ar-(4-(3-cyanophenyl)-5-(4-(trifluoromethy])phenoxy)thiazol-2-y])-2-(4- (ethylsulfonyl)phenyI)acetamide; Step 1:; To a solution of 3-acetylbenzonitrile (8 g) in chloroform (50 mL) and ethyl acetate (50 mL) was added copper(II) bromide (25.9 g). The reaction mixture was refluxed overnight. Solid was removed by filtration, and the filtrate was washed with sat. ammonium chloride and brine, dried, and concentrated to give 3-(2-bromoacetyl)benzonitrile (13 g) as a yellow oil. MS(ES?) m/z 225 (MH?).

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; GLAXO GROUP LIMITED; WANG, Yonghui; YANG, Ting; WO2012/100734; (2012); A1;,
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6136-68-1, Adding a certain compound to certain chemical reactions, such as: 6136-68-1, name is 3-Acetylbenzonitrile, 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 6136-68-1.

Step l :OSodium hydride (60% dispersion in oil, 8.27 g, 207 mmol, 3.00 equiv) was added to a solution of 3-acetylbenzonitrile (10.0 g, 68.9 mmol, 1 equiv) in tetrahydrofuran (300 mL). The reaction mixture was stirred at 60 C, and a solution of diethyl carbonate (12.5 mL, 103 mmol, 1.50 equiv) in tetrahydrofuran (60 mL) was added over 45 minutes. The light orange reaction mixture was stirred at 60 C for an additional 2 h, then was cooled to 22 C. Saturated aqueous ammonium chloride solution was added, and the mixture was concentrated to -1/2 volume by rotary evaporation. The resulting residue was partitioned between ethyl acetate and water. The organic layer was washed with saturated aqueous sodium chloride solution, and the washed solution was dried over sodium sulfate. The dried solution was filtered, and the filtrate was concentrated to afford ethyl 3-(3-cyanophenyl)-3-oxopropanoate (15 g, 100%) as a white solid. The crude reaction product was taken into the next step without further purification. Calcd(M+l)+: 218.1, Found: 218.0.

According to the analysis of related databases, 6136-68-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BROWN, William, Colby; HEIDEBRECHT, Richard, W.; BRUBAKER, Jason; FISCHER, Christian; HENDRIX, John, T.; KELLEY, Elizabeth, H.; MACCOSS, Rachel, N.; METHOT, Joey, L.; MILLER, Thomas; OTTE, Karin, M.; SILIPHAIVANH, Phieng; REGER, Thomas; WILLIAMS, Peter, D.; WISCOUNT, Catherine, M.; WO2011/46774; (2011); A1;,
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939-80-0, A common compound: 939-80-0, name is 4-Chloro-3-nitrobenzonitrile, belongs to nitriles-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Step 5 4-(Cyclohexylcarbamoylmethylamino)-3-nitrobenzonitrile Cyclohexylcarbamoylmethylcarbamic acid benzyl ester (16.359 g) was hydrogenated using 7.5% palladium carbon (3.24 g) in ethanol (164 ml) solution at atmospheric pressure over 8 hours. After completion of the reaction, the reaction mixture was filtered through celite, and the solvent was evaporated. The obtained residue was dissolved in a mixture of ethanol (50 ml) and isopropanol (50 ml). Thereto were added 4-chloro-3-nitrobenzonitrile (8.23 g) and triethylamine (7.1 ml), and the stirred under reflux for 6 hours. After completion of the reaction, water was added under reflux and the mixture was ice-cooled. The resultant solid was collected by filtration and washed successively with water and diisopropyl ether to give the title compound (10.211 g). 1H-NMR (delta ppm, CDCl3) 1.13 (m, 3H), 1.38 (m, 2H), 1.70 (m, 3H), 1.91 (m, 2H), 3.84 (m, 1H), 4.01 (d, J=5.4 Hz, 2H), 5.76 (brd, 1H), 6.81 (d, J=8.7 Hz, 1H), 7.65 (dd, J=2.1, 8.7 Hz, 1H), 8.54 (d, J=2.1 Hz, 1H), 8.81 (brtr, 1H).

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, 4-Chloro-3-nitrobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Japan Tobacco Inc.; US6562828; (2003); B1;,
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