Category: 3939-09-1

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. 3939-09-1, name is 2,4-Difluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 3939-09-1

4-Fluoro-2-(3-methyl-1H-1,2,4-triazol-1-yl)benzonitrile and 4-fluoro-2-(5-methyl-1H-1,2,4-triazol-1-yl)benzonitrile. A solution of 2,4-difluorobenzonitrile (7.07 g, 50.8 mmol) and 3-methyl-1H-1,2,4-triazole (4.22 g, 50.8 mmol) in N,N-dimethylformamide (45 ml) was treated with powdered anhydrous potassium carbonate (10 g) and the resulting mixture was stirred at 22 C. for 18 h. The solid was then filtered and the filtrate was concentrated in vacuo. The residue was diluted with ethyl acetate, washed with water and brine, dried over anhydrous magnesium sulfate and concentrated. The mixture containing the 2 and 4-triazolyl-benzonitriles was purified by a combination of chromatography on silica gel (elution gradient of ethyl acetate in hexane) and on reversed phase silica gel to give 1.86 g (18% yield) of 4-Fluoro-2-(3-methyl-1H-1,2,4-triazol-1-yl)benzonitrile and 0.526 g (5% yield) of 4-fluoro-2-(5-methyl-1H-1,2,4-triazol-1-yl)benzonitrile. 4-Fluoro-2-(3-methyl-1H-1,2,4-triazol-1-yl)benzonitrile. White crystals (ethyl acetate/hexanes). mp 117-118 C. 1HNMR 400 MHz (CDCl3) delta (ppm): 2.54 (3H, s, CH3), 7.24 (1H, m, CH), 7.62 (1H, dd, J=2.5 Hz and J=9.1 Hz, CH), 7.84 (1H, dd, J=5.6 Hz and J=8.6 Hz, CH), 8.82 (1H, s, CH). Anal. Calcd for C10H7FN4: C, 59.40; H, 3.49; N, 27.71. Found: C, 59.25; H, 3.32; N, 27.81. 4-fluoro-2-(5-methyl-1H-1,2,4-triazol-1-yl)benzonitrile. White crystals (ethyl acetate-hexane). mp 120-121 C. 1HNMR 400 MHz (CDCl3) delta (ppm): 2.56 (3H, s, CH3), 7.30 (1H, dd, J=2.5 Hz and J=8.1 Hz, CH), 7.39 (1H, m, CH), 7.91 (1H, dd, J=5.5 Hz and J=8.6 Hz, CH), 8.06 (1H, s, CH). Anal. Calcd for C10H7FN4: C, 59.40; H, 3.49; N, 27.71. Found: C, 59.35; H, 3.70; N, 27.77.

The synthetic route of 3939-09-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/129379; (2007); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

3939-09-1, Name is 2,4-Difluorobenzonitrile, 3939-09-1, 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.

To a solution of 2,4-difluorobenzonitrile (10 g, 72 mmol) dissolved in tetrahydrofuran (20 mL), and dimethylformamide (40 mL) was added 1,2,4-triazole sodium salt (6.3 g, 70 mmol) and the mixture stirred at 90 C. for 3 h after which the mixture was filtered and the solvent removed. The resulting residue was adsorbed onto silica gel and intermediates 67 and 68 separated by flash chromatography, eluting with 0% to 30% ethyl acetate/hexanes. 4-Fluoro-2-(1H-1,2,4-triazol-1-yl)benzonitrile. Colorless needles (2.46 g, 18% yield) 1H NMR (500 MHz, CDCl3) delta: 8.89 (1H, s), 8.19 (1H, s), 7.85 (1H, dd, J=8.7, 5.6 Hz), 7.60 (1H, dd, J=8.8, 2.4 Hz), 7.28-7.24 (1H, m). LCMS (M+H) calcd for C9H6N4F: 189.05. found: 189.13. 4-(1H-1,2,4-Triazol-1-yl)-2-fluorobenzonitrile. White solid (0.746 g, 6% yield) 1H NMR (500 MHz, CDCl3) delta: 8.66 (1H, s), 8.15 (1H, s), 7.79 (1H, dd, J=8.5, 6.7 Hz), 7.69 (1H, dd, J=9.5, 1.8 Hz), 7.65-7.63 (1H, m). LCMS (M+H) calcd for C9H6N4F: 189.05. found: 189.13. 4-Fluoro-2-(1H-1,2,4-triazol-1-yl)benzonitrile and 4-(1H-1,2,4-triazol-1-yl)-2-fluorobenzonitrile. To a solution of 2,4-difluorobenzonitrile (10 g, 72 mmol) dissolved in THF (20 mL), and DMF (40 mL) was added 1,2,4-triazole sodium (6.3 g, 70 mmol) and the mixture was stirred at 90 C. for 3 h, filtered and concentrated. The residue was adsorbed onto Silica gel and purified by flash chromatography eluting with 0%-10%-30% EtOAc/hexanes to give the 4-triazolyl isomer as colorless needles (2.46 g, 18%) and the 2-substituted isomer as a white solid (0.7455 g, 6%). 4-Fluoro-2-(1H-1,2,4-triazol-1-yl)benzonitrile. 1H NMR (500 MHz, CDCl3) delta: 8.89 (1H, s), 8.19 (1H, s), 7.85 (1H, dd, J=8.7, 5.6 Hz), 7.60 (1H, dd, J=8.8, 2.4 Hz), 7.28-7.24 (1H, m). LCMS (M+H) calcd for C9H6N4F: 189.05. found: 189.13. 4-(1H-1,2,4-triazol-1-yl)-2-fluorobenzonitrile. 1H NMR (500 MHz, CDCl3) delta: 8.66 (1H, s), 8.15 (1H, s), 7.79 (1H, dd, J=8.5, 6.7 Hz), 7.69 (1H, dd, J=9.5, 1.8 Hz), 7.65-7.63 (1H, m). LCMS (M+H) calcd for C9H6N4F: 189.05. found: 189.13.

Statistics shows that 2,4-Difluorobenzonitrile is playing an increasingly important role. we look forward to future research findings about 3939-09-1.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/129379; (2007); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 3939-09-1, name is 2,4-Difluorobenzonitrile, A new synthetic method of this compound is introduced below., 3939-09-1

Potassium nitrate (16.4 g, 147.4 mmol) was added to concentrated H2SO4 (85 ml, 1582 mmol) at 0 C, followed by slow addition of 2,4-difluorobenzonitrile (11.0 g, 79.1 mmol).The suspension was stirred at this temperature for an additional 4 hrs and quenched ice / water (800 ml). The resulting solid was collected by filtration and dried to give the title compound (13.8 g, 95%) as a white solid. NMR (400 MHz, CDCl3) 8.48 (m, IH), 7.24 (m, IH).

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; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/87530; (2006); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

3939-09-1, 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. 3939-09-1, name is 2,4-Difluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

1-(2-Cyano-5-fluoro-phenyl)-1H-1,2,4-triazole-3-carboxylic acid methyl ester. To a solution of methyl 1H-1,2,4-triazole-3-carboxylate (27 g, 215 mmol) in dimethylformamide (170 mL) was added sodium hydride (5.53 g, 95%, 217 mmol) and the mixture was stirred for 30 min. Added to this was 2,4-difluorobenzylnitrile (30 g, 217 mmol) and the resulting mixture stirred at room temp for 60 h. The mixture was diluted with water and filtered to remove solids. The solution was extracted with ethyl acetate and the organic phase was washed with water (3¡Á’s) and brine, then dried (Na2SO4) and concentrated. The resulting residue was purified by flash chromatography (SiO2) eluting with 30% tetrahydrofuran/20% CH2Cl2/50% hexane to give the title compound as white needles (5.34 g, 10% yield). 1H-NMR (300 MHz, CDCl3) delta ppm: 8.92 (1H, s), 7.85 (1H, dd, J=8.8, 5.5 Hz), 7.67 (1H, dd, J=8.8, 2.6 Hz), 7.34-7.27 (1H, m), 40.3 (3H, s). LCMS [M+H]+ calcd for C11H8N4FO2: 247.06. found: 247.11.

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; Bristol-Myers Squibb Company; US2007/129379; (2007); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

3939-09-1,Some common heterocyclic compound, 3939-09-1, name is 2,4-Difluorobenzonitrile, molecular formula is C7H3F2N, 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 solution of methyl 1H-1,2,4-triazole-3-carboxylate (27 g, 215 mmol) in dimethylformamide (170 mL) was added sodium hydride (5.53 g, 95%, 217 mmol) and the mixture was stirred for 30 min. Added to this was 2,4-difluorobenzylnitrile (30 g, 217 mmol) and the resulting mixture stirred at room temp for 60 h. The mixture was diluted with water and filtered to remove solids. The solution was extracted with ethyl acetate and the organic layer was washed with water (3X’s) and brine, then dried (Na2SO4) and concentrated. The resulting residue was purified by flash chromatography (SiO2) eluting with 30% tetrahydroftiran/20% CH2Cl2/50% hexane to give the title compound as white needles (5.34 g, 10% yield). 1H-NMR (300 MHz, CDCl3) delta ppm: 8.92 (1H, s), 7.85 (1H, dd, J=8.8, 5.5 Hz), 7.67 (1H, dd, J=8.8, 2,6 Hz), 7.34-7.27 (1H, m), 40.3 (3H, s). LCMS [M+H]+ calcd for C11H8N4FO2: 247.06; found: 247.11.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3939-09-1, its application will become more common.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/111984; (2007); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some common heterocyclic compound, 3939-09-1, name is 2,4-Difluorobenzonitrile, molecular formula is C7H3F2N, 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. 3939-09-1

Potassium tert-butoxide (216 ml, 1M in tetrahydrofuran, 216 mmol) was added to ice-cooled methanol (8.7 ml, 216 mmol), and the solution stirred for 40 minutes. The resulting suspension was added dropwise to a solution of 2,4-difluorobenzonitrile (30 g, 216 mmol) in tetrahydrofuran at -78 C. Once addition was complete the reaction was allowed to warm to room temperature and stirred for 18 hours. The reaction was diluted with hexane (200 ml) and the mixture washed with water (200 ml), brine (2*200 ml), then dried (MgSO4) and evaporated under reduced pressure. The residual solid was recrystallized from ethyl acetate:hexane to give the title compound, 9.8 g. 1H-NMR (CDCl3, 300 MHz) delta: 3.90 (s, 3H), 6.70 (m, 2H), 7.55 (dd, 1H). LRMS: m/z ES+ 152 [MH+]

The chemical industry reduces the impact on the environment during synthesis 2,4-Difluorobenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Barber, Christopher Gordon; Bunnage, Mark Edward; Harvey, John Wilson; Mathias, John Paul; US2005/20611; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

3939-09-1, 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. 3939-09-1, name is 2,4-Difluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of 2,4-difluorobenzonitrile (AI, 2.0 g, 28.7 mmol) in dry diethyl ether (250 mL), EtMgBr (10.5 mL, 3M solution in THF, 63.3 mmol) and Ti(0-iPr)4 (4.5 g, 31.5 mmol) were added at -78C. BF3.Et20 (10.7 mL, 57.4 mmol) was added and the reaction mixture was allowed to stirred at RT for 12 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was quenched with NH4C1 solution and extracted with EtOAc. The combined organic layer was washed with brine, dried over anhydrous Na2S04 and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography using 30% EtOAc/hexane to afford compound AJ (1.0 g, 20 %) as a pale yellow oil. LC-MS: m/z 170 [M+l]+.

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; VPS-3, INC.; YATES, Christopher, M.; (397 pag.)WO2018/165520; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

3939-09-1, name is 2,4-Difluorobenzonitrile, 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. 3939-09-1

Example 3 1-(2,4-Diamino-quinazolin-7-yl)-3,6,6-trimethyl-1,5,6,7-tetrahydro-indol-4-one (Compound 3); 2,4-Difluorobenzonitrile (2.78 g, 1 eq), guanidine hydrochloride (7.15 g, 3.74 eq), and sodium hydride (3.6 g, 7.6 eq) are added to dimethylacetamide (50 mL) and the resulting mixture is stirred at 150 C. for overnight. Then the reaction mixture is poured into sat’d NaHCO3 aq. solution (300 mL), extracted by EtOAc (3¡Á200 mL). The combined organic layers is dried over Na2SO4, filtered, concentrated. The crude product is purified by flash chromatography to give 7-Fluoro-quinazolin-2,4-diamine (1 g, 28% yield). LC/MS m/z=179 [M+H]+.

Statistics shows that 3939-09-1 is playing an increasingly important role. we look forward to future research findings about 2,4-Difluorobenzonitrile.

Reference:
Patent; Huang, Kenneth He; Veal, James; Barta, Thomas; Smith, Emilie D.; Ma, Wei; Ommen, Andy; US2008/70935; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts