Tag: M.W=200-300

Adding a certain compound to certain chemical reactions, such as: 138642-47-4, name is 2-Bromo-5-methoxybenzonitrile, 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 138642-47-4, Computed Properties of C8H6BrNO

B. Synthesis of 5-Methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile A mixture of 2-bromo-5-methoxybenzonitrile (82.6 g, 0.39 mol, 1 equiv), bis(pinacolato)diboron (109.1 g, 0.43 mol, 1.1 equiv) and potassium acetate (115.3 g, 1.17 mol, 3 equiv) in a mixture of 1,4-dioxane (400 mL) and DMSO (40 mL) was sparged with nitrogen for 1 hour. Pd(dppf)Cl2 (7.13 g, 5 mol %) was added and reaction mixture was gently heated at 60 C. for 2 hours then refluxed for 16 hours. The mixture was filtered through celite and the solids isolated from the filtrates were washed with isopropanol and heptanes to give the desired product as an off-white solid (57.41 g, 57% yield). Additional product (?10 g) was isolated from the filtrates.

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-Bromo-5-methoxybenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERSAL DISPLAY CORPORATION; BROOKS, Jason; SZIGETHY, Geza; MORELLO, Glenn; DENG, Jun; DJUROVICH, Peter I.; CHEN, Hsiao-Fan; (206 pag.)US2016/72082; (2016); A1;,
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Synthetic Route of 38791-62-7, 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. 38791-62-7, name is 4-Phenoxyphthalonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 1,2-Diisocyano-4-phenoxy benzene (8) (0.300 g, 1.36 ×10-3 mol) and phenol (0.356 g, 0.0375 mol) in THF was refluxed. The resultant product (9), 1,2-diisocyano-3,4-diphenoxy benzene,(0.300 g, 1.36 × 10-3 mol) was refluxed in 1-pentanol (14 mL)and 1 mol 1,8-diazabicyclo[5.4.0]-undec-7-ene (0.21 g, 1.36× 10-3 mol) for 16 h. Methanol (20 mL) was there after added and the precipitate (2a) filtered off, Soxhlet extracted with methanol and acetone and dried at 60 C. Yield = 0.294 g and yield (%) 43, Rf = 0.23 (ethyl acetate:hexane, 3:8). (KBr, numax,cm-1): 3620 (N-H), 2848 (C-H) aromatic, 1685 (C=C), 1163(C-H), 743 (C-H). UV-visible lambdamax (nm): 337, 606, 640, 661,702. 1H NMR (300 MHz, CDCl3) delta 2.01 (s, 2H, NH), 3.66 (m,4H, CH), 6.99 (m, 4H, ArH), 7.23 (m, 4H, ArH), 7.50 (m, 4H,ArH) 8.04 (m, 4H, ArH), 8.99 (m, 4H, ArH), 9.23 (m, 4H,ArH), 13C NMR (300 MHz, CDCl3) delta 71.01, 76.57, 76.99,77.41, 117.45, 119.69, 119.92, 126.95, 127.48, 127.63, 128.53,128.85, 128.94, 134.43, 135.20. Anal. calcd. C, 76.21; H, 4.19;N, 9.03. Found: C, 76.21; H, 4.18; N, 9.11.

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-Phenoxyphthalonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Isabirye, David A.; Seheri, Naledi H.; Aiyelabola, Temitayo O.; Asian Journal of Chemistry; vol. 29; 3; (2017); p. 489 – 495;,
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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. 1735-54-2, name is 4-Chloro-3-(trifluoromethyl)benzonitrile, A new synthetic method of this compound is introduced below., name: 4-Chloro-3-(trifluoromethyl)benzonitrile

a) 4-Chloro 3-trifluoromethyl-benzamidoxime The title compound was prepared from 4-chloro-3-trifluoromethyl-benzonitrile (617 mg, 3.00 mmol) and 0.576 M hydroxylamine hydrochloride in 95% ethanol (5.8 mL, 3.3 mmol) similar to Example 36c, and yielded 528 mg (74%) of white solid. 1H NMR (Acetone-d6): 9.29 (s, 1H), 8.15 (d, J=2.19 Hz, 1H), 8.00 (m, 1H), 7.69 (d, J=8.24 Hz, 1H), 5.73 (s, 2H).

The synthetic route of 1735-54-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Cai, Sui Xiong; Zhang, Han-Zhong; Drewe, John A.; Reddy, P. Sanjeeva; Kasibhatla, Shailaja; Kuemmerle, Jared Daniel; Ollis, Kristin P.; US2003/45546; (2003); A1;,
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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 133541-45-4 as follows. Computed Properties of C7H2BrF2N

To a stirred suspension of 4-bromo-2,5-difluorobenzonitrile (91 g, 417 mmol) and potassium carbonate (173 g, 1.25 mol) in N,N-dimethylformamide (910 ml) was added (S)-l,l,l- trifluoropropanol [CAS 3539-97-7] dropwise (52.4 g, 460 mmol). The resulting mixture was heated at 70 C for for 15 hours and cooled to room temperature. The reaction was concentrated and the residue was diluted with water. The aqueous solution was extracted with DCM (3x). The combined organic washes were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give an oil (136.6 g). The residue was triturated with a mixture of hexanes and toluene (9:1, 200 mL) to give the desired product as a white solid (90.3 g, 93% purity, 64% yield). LC-MS (Method A): R, = 1.29 min; MS (ESIpos): m/z = 312.0 [M+H]+. 1H-NMR (400 MHz, CHLOROFORM-d) d [ppm] : 1.511 (4.41), 1.531 (15.64), 1.533 (16.00), 1.548 (15.84), 1.550 (15.83), 4.566 (1.08), 4.581 (2.68), 4.597 (3.18), 4.612 (2.62), 4.626 (1.01), 7.194 (5.27), 7.207 (7.60), 7.220 (7.57).

According to the analysis of related databases, 133541-45-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; JANZER, Andreas; POLITZ, Oliver; EHEIM, Ashley, Lakner; (87 pag.)WO2019/197269; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 362527-61-5, name is Ethyl 3-bromo-4-cyanobenzoate, 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 362527-61-5, COA of Formula: C10H8BrNO2

EXAMPLE 2; Preparation of 3-Bromo-4-cyanobenzoic acid; A solution of ethyl 4-amino-3-bromobenzoate (23.5 g, 96.3 mmol) in methylene chloride at -10 C. is treated dropwise with tert-butyl nitrite (14.0 mL, 118.4 mmol), followed by boron trifluoride diethyl etherate (18.4 mL, 146.5 mmol). The reaction mixture is allowed to come to room temperature, stirred for 4 h, diluted with ethyl ether and filtered. The filtercake is dried, dispersed in toluene, cooled to 0 C., treated with a solution of copper (I) cyanide (11.5 g, 129.2 mmol) and sodium cyanide (15.8 g, 323.1 mmol) in water, stirred at 0 C. for 30 min., warmed to 60 C., stirred for 1 h, cooled to room temperature and diluted with EtOAc and water. The organic phase is separated, dried over MgSO4 and concentrated in vacuo. The resultant residue is crystallized from ethyl ether/hexanes to give the ethyl ester of the title compound as an off-white solid, 18.6 g (76% yield). A solution of this ester (8.5 g, 33.6 mmol) in THF is treated with a solution of NaOH (30 mL, 2.5 N) and ethanol, stirred for 20 h, acidified with 2N HCl and extracted with ethyl ether. The ether extracts are combined, dried over MgSO4 and concentrated in vacuo. The resultant residue is crystallized from ethyl ether/hexanes to afford the title compound as a beige solid, 6.81 g (90% yield), identified by HNMR and mass spectral analyses. MS m/e 223 (M-H)+; 1H NMR (400 MHz, DMSO-d6) delta 8.05 (dd, J=9.76, 1.37 Hz 1 H), 8.09 (d, J=8.08 Hz, 1H), 8.29 (d, J=1.37 Hz, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 3-bromo-4-cyanobenzoate, and friends who are interested can also refer to it.

Reference:
Patent; Wyeth; US2005/282825; (2005); 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. 186517-05-5, name is 2,3-Difluoro-6-(trifluoromethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H2F5N

Example 12 2-chloro-3-fluoro-6-trifluoromethylbenzonitrile (Compound No. 33) STR29 To a solution of 50.9 g of 2,3-difluoro-6-trifluoromethylbenzonitrile in 240 ml of dimethyl sulfoxide (DMSO) was added 53.3 g of calcium chloride and the mixture was stirred for 6 hours at a temperature of from 140 to 150 C. After cooling, the reaction mixture was further added with 240 ml water and extracted with 240 ml and 100 ml hexane twice. The organic layer obtained was dried over anhydrous magnesium sulfate, and the solvent therein was distilled under reduced pressure. The crude product obtained was distilled under reduced pressure to obtain 38.9 g of the title compound.

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 186517-05-5.

Reference:
Patent; Nippon Soda Co., Ltd.; US6054605; (2000); 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. 66389-80-8, name is tert-Butyl 4-cyanobenzylcarbamate, A new synthetic method of this compound is introduced below., Recommanded Product: 66389-80-8

c) N-Boc-4-aminomethyl-N-hydroxy-benzamidine; To a solution of N-Boc-4-aminoethylbenzonitrile (14g; 60mmol) in THF (500ml) is added at 50C a solution of hydroxy Ia mine in water (1/1 ; 80ml; 1.8 mol). The reaction mixture is then stirred at room temperature for 16 hours. The reaction mixture is diluted with water and THF is removed under vacuo. The resulting precipitate is collected by filtration and dried. Pure title compound is obtained by recrystallization from diethylether.

The synthetic route of 66389-80-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; WO2008/37476; (2008); A1;,
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Synthetic Route of 138642-47-4, 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. 138642-47-4 name is 2-Bromo-5-methoxybenzonitrile, 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 a mixture of 2-Bromobenzonitrile (183.4 mg, 1 mmol), benzaldehyde (210.5 mg, 2 mmol),CuCl2 (17.2 mg, 0.1 mmol), Cs2CO3 (652.2 mg, 2 mmol), and L-proline (23.2 mg, 0.2 mmol) in H2O(2 mL) was added 27% aqueous ammonia (1 mL) in a tube under air atmosphere. Then the tubewas sealed, and the mixture was stirred at 100 C for 12 h. Next, the tube was opened to air and themixture was stirred at 100 C for another 12 h. After being cooled to room temperature, the resultingmixture was quenched with NH4Cl solution and extracted with ethyl acetate. The combined organiclayer was washed with brine, and then dried over anhydrous Na2SO4. The solvent was evaporatedunder reduced pressure and the crude product was purified by chromatography on silica-gel to afford2-phenylquinazolin-4(3H)-one (4aa) in 75% isolated yield.

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

Reference:
Article; Liu, Zibin; Zeng, Li-Yan; Li, Chao; Yang, Fubiao; Qiu, Fensheng; Liu, Shuwen; Xi, Baomin; Molecules; vol. 23; 9; (2018);,
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Adding a certain compound to certain chemical reactions, such as: 66389-80-8, name is tert-Butyl 4-cyanobenzylcarbamate, 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 66389-80-8, Product Details of 66389-80-8

Zn(OTf)2, 0.27g (2.5 mmol) of formamidine acetate, 58mg (0.25 mmol) nitrile ,0.20 mL DMF, and 0.40 mL (12.5 mmol) of anhydrous hydrazine was added. The vessel was sealed and the mixture was stirred in an oil bath at 30C for 36 hours. The reaction solution was cooled to room temperature and the seal was removed. Sodium nitrite (5.0 mmol, 345 mg) in 5 mL of water was slowly added to the solution and followed by slow addition of 1M HCl during which the solution turned bright red in color and gas evolved. Addition of 1M HCl continued until gas evolution ceased and the pH value is 3. (Caution: this step generates a large amount of toxic nitrogen oxide gasses and should be performed in a well ventilated fume hood). The mixture was extracted with EtOAc and the organic phase dried over sodium sulfate. The EtOAc was removed using rotary evaporation and the residue purified using silica column chromatography (Hexane:EtOAc=7: l) to give 50mg product as red solid, the yield is 70%. 1H NMR (500 MHz, CDC13) delta 1.49 (9H, s), 4.45 (2H, d, J = 5 Hz ), 4.97 (1H, bs), 7.53 (2H, d, J = 10 Hz), 8.60 (2H, d, J = 10 Hz), 10.21 (1H, s); 13C MR (125 MHz, CDC13) delta 39.07, 51.82, 118.84, 119.19, 120.76, 132.11, 141.12, 142.56, 149.36; HRMS [M+Na]+ m/z calcd. for [C9H16N502]+ 310.1276, found 310.1274.

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; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; DEVARAJ, Neal, K.; YANG, Jun; SECKUTE, Jolita; WO2013/152359; (2013); A1;,
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Reference of 133541-45-4, 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. 133541-45-4 name is 4-Bromo-2,5-difluorobenzonitrile, 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.

(c) 4-Bromo-2-[[(1R)-3-chloro-1-phenylpropyl]oxy]-5-fluorobenzonitrile This was prepared by the method of Example 43(a) using 4-bromo-2,5-difluorobenzonitrile and (R)-alpha-(2-chloroethyl)benzenemethanol. 1H NMR 300 MHz (CDCl3) 8.02 (1H, s), 7.42-7.26 (5H, m), 7.06-7.03 (1H, m), 5.46-5.43 (1H, m), 3.82-3.62 (1H, m), 3.75-3.60 (1H, m), 2.75-2.5 (1H, m), 2.55-2.30 (1H, m).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-2,5-difluorobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Cheshire, David; Connolly, Stephen; Cox, David; Hamley, Peter; Mete, Antonio; Pimm, Austen; US2003/158185; (2003); A1;,
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