Category: nitriles-buliding-blocks

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. 17354-04-0, name is 2-(4,5-Dimethoxy-2-nitrophenyl)acetonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-(4,5-Dimethoxy-2-nitrophenyl)acetonitrile

General procedure: Piperidine (0.03 ml, 5 mol %) was added to a warm solution of the appropriate salicylaldehyde 5 (5 mmol) and 2-(4,5-dimethoxy-2-nitrophenyl)acetonitrile (1.12 g, 5 mmol) in EtOH (10 ml). The resulting solution was refluxed with stirring for 5 h. The mixture was treated with a solution of concentrated H2SO4 (0.55 ml) in EtOH (2 ml) and refluxed with stirring for 2 h. The obtained precipitate was filtered, washed with EtOH (10 ml), hot H2O (40 ml) and finally with EtOH (10 ml), and dried at 100 C.

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:
Article; Irgashev, Roman A.; Karmatsky, Arseny A.; Slepukhin, Pavel A.; Rusinov, Gennady L.; Charushin, Valery N.; Tetrahedron Letters; vol. 54; 42; (2013); p. 5734 – 5738;,
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Adding a certain compound to certain chemical reactions, such as: 455-18-5, name is 4-(Trifluoromethyl)benzonitrile, 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 455-18-5, Computed Properties of C8H4F3N

General procedure: To an oven-dried 15 mL sealed tube were added 2-aminophenylmethanol 1 (0.425 mmol), benzonitrile 2(0.25 mmol), Ru cat. b (1.94 mg, 1 mol%), and KOtBu (14.02 mg, 0.5equiv) intamyl alcohol (1 mL) under an air atmosphere. The sealedtube was capped and heated at 130C for 2 h. The reaction mixturewas cooled down to room temperature and directly concentratedunder vacuum. The crude mixture was puried by preparative thin-layer-chromatography (petroleum ether/ethyl acetate 20/1) togive the desired product 3 or 4.

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-(Trifluoromethyl)benzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Wan, Xiao-Min; Liu, Zi-Lin; Liu, Wan-Qing; Cao, Xiao-Niu; Zhu, Xinju; Zhao, Xue-Mei; Song, Bing; Hao, Xin-Qi; Liu, Guoji; Tetrahedron; vol. 75; 18; (2019); p. 2697 – 2705;,
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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. 16532-79-9, name is 4-Bromophenylacetonitrile, A new synthetic method of this compound is introduced below., Formula: C8H6BrN

This compound was prepared via Method C using 5-amino-pyridine-2-carboxylic acid methylamide prepared by Method N and 2-Methyl-2-[4-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)- phenyl]-propionitrile prepared by Method O followed by Method R. Method O: [00305] NaH (2.5 eq.) is added to (4-Bromo-phenyl)-acetonitrile (leq) in DMF at O0C. The reaction mixture is stirred for 200C. MeI is added to the resulting solution at O0C. The resulting mixture is stirred at room temperature for 19hrs. EtOAc and water are added to the reaction. The organic phases are isolated, dried over MgSO4, filtered and evaporated under vacuum to afford the expected product. Purification by flash chromatography may be required to afford the pure product.

The synthetic route of 16532-79-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GALAPAGOS NV; MENET, Christel, Jeanne, Marie; BLANC, Javier; HODGES, Alastair, James; BURLI, Roland, Werner; BRECCIA, Perla; BLACKABY, Wesley, Peter; VAN ROMPAEY, Luc, Juliaan, Corina; FLETCHER, Stephen, Robert; WO2010/10184; (2010); A1;,
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Reference of 5414-21-1, 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. 5414-21-1, name is 5-Bromovaleronitrile, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A solution of m-tolylmagnesium bromide 26, prepared from 416 muL of 3-bromotoluene and 83 mg of magnesium turnings in anhydrous THF (3 mL), was added dropwise under inert atmosphere to a solution of 5-bromovaleronitrile (400 muL, 3.43 mmol) in anhydrous THF (3 mL). The mixture was stirred at room temperature for 1 h, quenched with a saturated aqueous solution of NaHCO3 (3 mL) and extracted with dichloromethane (3 * 10 mL). The combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure. The crude residue was purified by silica gel column chromatography (dichloromethane/methanol 95:5) to provide the compound 7 as a yellow oil (225 mg, 38% yield). Rf = 0.40 (dichloromethane/methanol 95:5). 1H NMR: delta 1.63-1.71 (m, 2H), 1.79-1.87 (m, 2H), 2.37 (s, 3H), 2.60-2.66 (m, 2H), 3.80-3.86 (m, 2H), 7.18-7.29 (m, 2H), 7.51-7.54 (m, 1H), 7.61-7.62 (m, 1H). 13C NMR: delta 20.0, 21.7, 22.1, 27.4, 50.1, 123.3, 126.8, 128.3, 130.5, 138.1, 140.4, 166.2. MS (ESI) m/z [M+H]+ Calcd for C12H16N+: 174.13. Found: 174.2.

The chemical industry reduces the impact on the environment during synthesis 5-Bromovaleronitrile. I believe this compound will play a more active role in future production and life.

Reference:
Article; Matera, Carlo; Quadri, Marta; Sciaccaluga, Miriam; Pome, Diego Yuri; Fasoli, Francesca; De Amici, Marco; Fucile, Sergio; Gotti, Cecilia; Dallanoce, Clelia; Grazioso, Giovanni; European Journal of Medicinal Chemistry; vol. 108; (2016); p. 392 – 405;,
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Synthetic Route of 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.

4-(1-Cyanocyclopentyl)benzonitrile [S11]. In a flamed dried 50 mL flask, 710.8 mg (5.0 mmol) of 2-(4-cyanophenyl)acetonitrile was dissolved in 7.5 mL anhydrous DMF. 316.0 mg (95% purity, 12.5 mmol, 2.5 equiv.) of NaH was added in portions at 0 C. and the reaction was allowed to stir for 1 hour at 0 C. 1.0797 g (0.59 mL, 5.0 mmol, 1.0 equiv.) of 1,4-dibromobutane was added dropwise at 0 C. and the reaction was allowed to stir overnight at room temperature. The reaction was quenched carefully with -10 mL water and extracted with 30 mL EtOAc three times. The combined organic layer was washed with 50 mL brine, dried with MgSO4, filtered, and concentrated. Flash column chromatography on silica (50 mm fritted glass column, 300 mL SiO2) using 5% EtOAc/hexanes?10% EtOAc/hexanes as eluent gave 880.1 mg (4.48 mmol) of pure product as a colorless oil (90% yield). 1H-NMR (500 MHz, CDCl3) delta 7.69-7.67 (m, 2H), 7.59-7.57 (m, 2H), 2.52-2.48 (m, 2H), 2.09-1.94 (m, 6H). 13C-NMR (126 MHz, CDCl3) delta 145.2, 132.8, 127.0, 123.3, 118.3, 112.0, 48.0, 40.7, 24.5. HRMS (EI+) m/z calculated for C13H12N2 [M]+: 196.1000, found 196.1004.

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-(Cyanomethyl)benzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; The Board of Trustees of the University of Illinois; WHITE, M. Christina; ZHAO, Jinpeng; (94 pag.)US2020/87331; (2020); A1;,
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Adding a certain compound to certain chemical reactions, such as: 1558-81-2, name is Ethyl 1-Cyano-1-cyclopropanecarboxylate, 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 1558-81-2, Recommanded Product: Ethyl 1-Cyano-1-cyclopropanecarboxylate

To a mixture of ethyl 1-cyanocyclopropanecarboxylate (35.9mmol, 5g), dimethoxyethane (10OmL) and methanol (1OmL) was added sodium borohydride (287mmol, 10.87g) slowly and the mixture stirred at room temperature for 18 hours. The solution was diluted with saturated sodium hydrogen carbonate slowly and then extracted with 10% methanol / dichloromethane (x3). The organic layers were combined, dried over sodium sulphate and concentrated under vacuum to give the intermediate 1-(hydroxymethyl)cyclopropanecarbonitrile (2.36g). 1 H NMR (CDCI3, 400 MHz): delta 0.99 (2H, m), 1.28 (2H, m), 2.5 (1 H, br s), 3.62 (2H, s)

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, Ethyl 1-Cyano-1-cyclopropanecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; N.V. ORGANON; WO2009/24550; (2009); A1;,
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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. 78473-00-4, name is 4-Amino-3,5-dichlorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., name: 4-Amino-3,5-dichlorobenzonitrile

3,5-Dichloro-4-aminobenzylamine To lithium aluminum hydride (0.57 g, 15 mmol) in dry THF (20 mL) was added dropwise 3,5-dichloro-4-aminobenzonitrile (1.87 g, 10 mmol) in THF (30 mL). The mixture was stirred at rt for 2 h. Then, sodium sulfate decahydrate (4.83 g, 15 mmol) was added and the mixture was stirred for 30 min. The solid was filtered off and washed with THF three times. The solvent was removed under vacuum and the residue was purified by chromatography with Methanol/DCM (3:7) as the eluant. 3,5-Dichloro-4-aminobenzylamine was obtained as an off-white solid (1.5 g, 80%). 1H NMR (300 MHz, CD3OD): delta3.65 (s, 2H), 7.2 (s, 2H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 78473-00-4.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/232581; (2007); A1;,
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Related Products of 243128-37-2, A common heterocyclic compound, 243128-37-2, name is 4-Fluoro-3-methoxybenzonitrile, molecular formula is C8H6FNO, 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.

Step A. Under an argon atmosphere a mixture of commercially available 4-fluoro- 3-methoxybenzonitrile (5.O g), AlCl3 (8.8 g) and NaCl (1.94 g) was heated (melted) to 190C for 45 min, cooled, poured on ice (200 mL) and extracted with CHCI3 (3 x). The combined organic phases were washed with H2O, dried (MgSO4), filtered, concentrated and purified by chromatography (silica, cyclohexane/EtOAc 9:1 to 8:1) to afford the title compound as colorless needles (3.45 g, 76%). [MH]+ = 138.

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; ALANTOS PHARMACEUTICALS HOLDING, INC.; WO2008/63671; (2008); A2;,
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Reference of 16532-79-9,Some common heterocyclic compound, 16532-79-9, name is 4-Bromophenylacetonitrile, molecular formula is C8H6BrN, 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.

Step a) intermediate 20 Synthesis of 2-(4-bromophenyl)-2-methylpropanenitrile.The preparation of 2-(4-bromophenyl)-2-methylpropanenitrile is carried out as described in J. Med. Chem. (1995), no 38, page 1608-1628. Sodium Hydride (60% susp. in oil, 6.66 g, 166.3 mmol) is added in many portions over 1 hour to 2-(4-bromophenyl)-acetonitrile (1Og, 51.0 mmol), dissolved in anhydrous DMF and methyl iodide (14.838g, 102.0 mmol) at 0 0C. This solution turns to a thick and brown orange paste. It is left stirring to slowly warm up to room temperature (18h). The organic solution is partitioned between water and ethyl acetate, separated, dried over anhydrous sodium sulfate and filtered. The solution is concentrated under reduced pressure and the resulting crude is purified on silicagel using a 0 to 20 % ethyl acetate in hexane gradient to yield the desired compound (4.9 g, 42%) as a clear oil. IH NMR (400 MHz, CHLOROFORM-D) delta ppm 1.71 (s, 6 H) 7.35 (d, /=8.79 Hz, 2 H) 7.52 (d, /=8.79 Hz, 2 H)

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

Reference:
Patent; ASTRAZENECA AB; WO2008/18827; (2008); A1;,
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Adding a certain compound to certain chemical reactions, such as: 4640-66-8, name is 4-Chlorophenacylcyanide, 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 4640-66-8, Recommanded Product: 4-Chlorophenacylcyanide

Add Na2CO3 (0.25 mmol) to a 25 mL reaction flask,a compound (0.5 mmol) represented by the formula m1,a compound of formula m2 (0.5 mmol) and acetonitrile (3 mL),The reaction was carried out at 90 C for 24 h, and the reaction was followed by thin layer chromatography.After the reaction was completed, the solvent was evaporated under reduced pressure and ethyl acetate was dissolved.Separation on a silica gel column (developing solvent petroleum ether / ethyl acetate volume ratio = 6:1) afforded white solid compound A13.(The structural formula of the compound A13 is as shown by m3,The nuclear magnetic resonance spectrum is shown in Figure 11.The nuclear magnetic carbon spectrum is shown in Figure 12.The synthesis reaction formula is shown in Fig. 25, and the yield is 55%).

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:
Patent; Anhui Normal University; Li Qianqian; He Xinwei; Tao Jiajia; Shang Yongjia; (26 pag.)CN108440467; (2018); A;,
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