Tag: M.W=200-300

Electric Literature of 79463-77-7, 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. 79463-77-7, name is Diphenyl N-cyanocarbonimidate belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Alternatively, a mixture of 2n (4.46 g, 21.3 mmol) and diphenylcyanocarbimidate (5.07 g, 21.3 mmol) in 2-PrOH (100 mL) was stirred at ambient temperature under N2 for 20 h. The solids that formed were collected by filtration and washed with 2-PrOH to afford 3k (5.90 g, 78%) as an off-white solid: 1H NMR (300 MHz, DMSO-d6) delta 10.82 (s, 1 H), 7.50-7.37 (m, 2H), 7.32-7.26 (m, 4H), 7.08-7.03 (m, 2H), 6.82 (dd, J = 7.9, 1.9 Hz, 1H), 4.98 (t, J = 4.9 Hz, 1 H), 4.07 (t, J = 6.5 Hz, 2H), 3.93-3.76 (m, 4H), 2.06-2.00 (m, 2H).

The synthetic route of Diphenyl N-cyanocarbonimidate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RIGEL PHARMACEUTICALS, INC.; WO2007/30680; (2007); A2;,
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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 1835-65-0 as follows. name: 3,4,5,6-Tetrafluorophthalonitrile

With reference to Compounds 17 and 18, an exemplary synthesis and characterization of F34PcCo (hereinafter “Compound 17”) and F52Pc’Co (hereinafter “Compound 18”) is depicted. In particular, Compounds 17 and 18 are prepared similarly to Compounds 15 and 16, using sixteen (16) glass vessels, each charged with about 0.3 g (about 0.47 mmol) of Compound 14, about 0.05 g (about 0.25 mmol) of Compound 13 and about 0.045 g (about 0.18 mmol) cobalt(II) acetate tetrahydrate. Microwave heating is performed for approximately 12 min at about 185 ¡ãC. Initial purification of the brute solid by gel filtration is done with a toluene hexane approximately 1 :9 mixture (v/v). The rest of the separations are carried out as described for Compounds 1 and 16. Evaporation of the eluted fractions and drying to constant weight allows for isolation of green exemplary F52Pc’Co (Compound 18) in about 1.5percent yield (about 0.05 g), exemplary F34PcCo (Compound 17) in about 1 1 percent yield (about 0.19 g) and exemplary F]6PcCo as a side product in about 10percent yield (about 0.084 g), based on starting material Compound 13. About 4.5 g of Compound 14 are recovered following the initial separation (about 90percent of initial amount). X-ray quality single crystals for exemplary F34PcCo are obtained by slow evaporation of an acetonitrile/toluene approximately 1 :1 solution.[00106] Specifically, the exemplary properties of Compound 17, i.e., F34PcCo, are as follows: Mp > 300 ¡ãC; UV-vis (CHCI3): lmm (log e) 680 (4.52), 667 (4.50), 61 1 (4.03) nm (L moF1 cm-1); 19F NMR (282 MHz, (CD3)2CO): delta -63.58 (3F, br, GF3), -67.36 (3F, s, CF3), -68.75 to -76.79 (12F, m, CF3), -100.98 (I F, br, Ar-F), -132.36 (I F, s, CF), -137.64 (I F, d, Ar-F), -139.44 to -142.63 (5F, m, Ar-F), -155.92 to -157.62 (6F, m, Ar-F), -165.55 (I F, d, CF), -169.46 (IF, br, CF); HRMS (APCI-): calcd. for [M]~ (C41F34N8C0) 1308.9040, found 1308.9032.[00107] With reference to FIG. 17, the measured exact mass spectrum (negative ion APCI) and isotope pattern of [M]~ for F34PCC0 are depicted, indicating the calculated value for [M]~.[00108] Turning now to FIG. 18(a), the side view of the aggregation in solid state of F34PCC0 is illustrated. In particular, the toluene molecules in the crystalline lattice and the H atoms of coordinated acetonitrile have been omitted and the Z-C3F7 groups are depicted as van der Waals spheres. The interplanar stacking distance, approximately 3.25 A, illustrates the existence of pi-pi interactions. With reference to FIG. 18(b), a top view of the pi-pi stacking region of two adjacent molecules of F34PCC0 is depicted.[00109] With reference to FIG. 19, the X-ray structure of F34PcCo(CH3CN) is depicted, showing a metal-coordinated acetonitrile molecule. In particular, the thermal ellipsoids are plotted at about 40percent probability and rotational disorder of the CF3 groups of -C3F7 is present, as is shown by the dashed lines.[00110] Further, the exemplary properties of Compound 18, i.e., Fs2Pc’Co, are as follows: Mp > 300 ¡ãC; UV-vis (CHC13): max (log e) 686 (4.62), 615 (4.1 8), 334 (4.58) nm (L mol”1 cm”1); l9F NMR (282 MHz, (CD3)2CO): delta -63.62 (3F, br, C73/4, -67.01 to -76.28 (33F, m, CF3), -90.0 to -1 10.0 (2F, br, Ar-F), -137.5 to -147.5 (6F, m, Ar-F), -155.0 to – 1 59.5 (4F, br, Ar-F), -165.82 (I F, m, CF), -169.76 to -171.73 (3F, m, CF); HRMS (APC1-): calcd. for [M]~ (C5oF52NgCor 1758.8753, found 1758.8763.[00111] With reference to FIG. 20, the measured exact mass spectrum (negative ion APCI) and isotope pattern of [M]~ for F52Pc’Co are depicted, indicating the calculated value for [Mf.[00112] Turning now to FIG. 21 (a), a ball-and-stick representation ofF34PcZn(H20)*((CH3)2CO)2 is depicted showing H-bonding between the H atoms of H20 and the oxygen atoms (02) of the two acetone molecules. FIG. 21(b) is a van der Waals representation of the exemplary F3 PcZn(H20)*((CH3)2CO 2. FIG. 21(c) illustrates the side view of the aggregation in solid state of exemplary p34PcZn. The acetone molecules in the crystalline lattice and the H atoms of coordinated H2O have been omitted for clarity. The i-C3F7 groups are depicted as van der Waals spheres. The interplanar stacking distance, about3.393 A, demonstrates the existence of pi-pi interactions. Further, FIG. 21 (d) illustrates a top view of the pi-pi stacking region of two adjacent molecules of exemplary F34PCZ11. [0PsiPi3] Turning now to FIG. 22, the X-ray structure of F3 Pc2n(H20) is illustrated, showing a metal -coordinated water molecule. In particular, the acetone molecules in the crystalline lattice have been omitted. The thermal ellipsoids of FIG. 22 are plotted at about 40percent probability.

According to the analysis of related databases, 1835-65-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NEW JERSEY INSTITUTE OF TECHNOLOGY; GORUN, Sergiu, M.; LOAS, Andrei, Ioan; GRISWOLD, Kimberly; LAPOK, Lukasz; PATEL, Hemantbhai, Hasmukhbhai; GERDES, Robert; WO2012/61344; (2012); 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. 70591-86-5, name is 3-Bromobenzoylacetonitrile, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H6BrNO

Intermediate 2 (0092) 3-(3-bromophenyl)-lH-pyrazol-5-amine A mixture of 3-(3-bromophenyl)-3- oxopropanenitrile (35 g, 156 mmol) and hydrazine hydrate (11.34 mL, 234 mmol) in ethanol (600 mL) was refluxed for 16 h. Mixture was then cooled and concentrated in vacuuo. Crude product was diluted with dichloromethane and stirred for 5 min. Solids were filtered and dried to afford 3-(3-bromophenyl)-lH-pyrazol-5-amine (30 g, 126 mmol, 81 % yield) as off-white solid. 1H NMR (400 MHz, DMSO-d6) delta 12.02 (br. s., 0.4H), 11.66 (br. s., 0.6H), 7.86 (t, J=1.6 Hz, 1H), 7.67 (d, J=7.5 Hz, 1H), 7.45 (d, J=6.8 Hz, 1H), 7.37 – 7.18 (m, 1H), 5.78 (br. s., 1H), 5.08 (br. s., 1.2H), 4.68 (br. s., 0.8H). LCMS (M+H) = 240.1.

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 70591-86-5.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PEESE, Kevin; WANG, Zhongyu; LANGLEY, David, R.; KADOW, John, F.; NAIDU, Narasimhulu, B.; WO2015/123182; (2015); A1;,
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Electric Literature of 13338-63-1, These common heterocyclic compound, 13338-63-1, name is 3,4,5-Trimethoxyphenylacetonitrile, 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.

Using the method of synthesizing an intermediate similar to that of Example 1,Take 0.01 mol of 3,4,5-trimethoxyphenylacetonitrile (5), 0.01 mol of 4-chlorobenzaldehyde and 20 mL of methanol into a 50 mL three-necked flask.Stirring to 60 C, adding 0.005 mol of sodium methoxide, constant temperature reaction 4-6 h,TLC scanning and detection, after the reaction is completed, it is cooled to room temperature, filtered, washed with water, dried, and recrystallized from methanol to obtain a pale yellow solid.Yield: 59.3%,

Statistics shows that 3,4,5-Trimethoxyphenylacetonitrile is playing an increasingly important role. we look forward to future research findings about 13338-63-1.

Reference:
Patent; Yanbian University; Bu Gonggaofamingren; (14 pag.)CN108503561; (2018); A;,
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Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 52805-37-5, name is 3-(Benzyloxy)-4-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 52805-37-5, Recommanded Product: 3-(Benzyloxy)-4-methoxybenzonitrile

A solution of 3-benzyloxy-4-methoxybenzonitrile 3 (0.81 g, 3.38 mmol) in glacial acetic acid (3.2 mL) was added dropwise to concentrated nitric acid (70 %, 8 mL) with cooling in ice-bath. Once the addition was complete, the reaction was stirred for a further 1 h, after which time the mixture was poured into water. The resulting precipitate was isolated by filtration and washed with water to afford the solid. The solid was dissolved in dichloromethane. The solution was washed with water, dried (Na2SO4), and evaporated to give a product 4 (0.70 g, 2.46 mmol) in 73% yield. 1H NMR (400 MHz, CDCl3, delta): 7.80 (s, 1H), 7.46-7.36 (m, 5H), 7.23 (s, 1H), 5.25 (s, 2H), 4.03 (s, 3H); 13C NMR (100.6 MHz, CDCl3, delta): 152.6, 152.4, 142.8, 134.3, 129.0, 128.9, 127.4, 117.0, 115.5, 108.1, 100.6, 71.7, 56.8; IR (KBr): 2223, 1567, 1529, 1340, 1295, 750, 696 cm-1; MS m/z: 285.0 (M+1, 25.4), 154.0 (100.0), 136.0 (85.6), 107.0 (39.6), 91.0 (67.3), 77.0 (47.9); HRMS-FAB (m/z): [M+1]+ calcd for C15H13N2O4, 285.0875; found, 285.0870.

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

Reference:
Article; Yin, Kai-Hao; Hsieh, Yi-Han; Sulake, Rohidas S.; Wang, Su-Pei; Chao, Jui-I.; Chen, Chinpiao; Bioorganic and Medicinal Chemistry Letters; vol. 24; 22; (2014); p. 5247 – 5250;,
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Adding a certain compound to certain chemical reactions, such as: 36282-26-5, name is 2-Bromo-4-fluorobenzonitrile, 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 36282-26-5, COA of Formula: C7H3BrFN

To a solution of 2-bromo-4-fluorobenzonitrile (5.0 g, 25.0 mmol) in anhydrous THF (20 mL) is added PrMgCl 2.0M in THF (15.0 mL, 30.0 mmol) at -30C. The solution is stirred at -30 C for 3 hours and DMF (5.80 mL, 75.0 mmol) is added. The reaction mixture is allowed to warm to room temperature and is stirred for 1 hour. The solution is cooled to -10C, 2M hydrochloric acid (37 mL) is added and the solution is stirred for 20 minutes. The solution is concentrated in vacuo to -1/3 original volume and extracted into EtOAc (3x). The combined organics are then dried (Na2S04), filtered and concentrated to afford 4-fluoro-2-formyl benzonitrile (3.9 g, 71%).

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-4-fluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; CHEN, Zhidong; HAO, Ming-Hong; LIU, Weimin; LO, Ho-Yin; LOKE, Pui Leng; MAN, Chuk, Chui; MORWICK, Tina, Marie; NEMOTO, Peter, Allen; TAKAHASHI, Hidenori; TYE, Heather; WU, Lifen; WO2011/68821; (2011); A1;,
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These common heterocyclic compound, 36282-26-5, name is 2-Bromo-4-fluorobenzonitrile, 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. name: 2-Bromo-4-fluorobenzonitrile

To a stirred solution of 2-bromo-4-fluorobenzonitrile (5 g, 25 mmol) in ether (100 mL) was added MeMgBr (25 mL, 75 mmol) at room temperature. The solution was stirred at room temperature for 0.5 hour before Ti(Oi-Pr)4 (41 mL, 25 mmol) was added and the resulting mixture was heated to reflux for 6 hours. Aqueous NaOH (10%, 200 mL) solution was then slowly added to the reaction mixture at 0 C and the reaction mixture was stirred at room temperature for additional 30 minutes. After dilution with aq. Na2C03 (5%, 400 mL) solution, it was extracted with t-BuOMe (100 mL x 3). The combined organic layers were concentrated under reduced pressure. The residue obtained was diluted with aq. HC1 solution (5%) and the aqueous layer was washed with t-BuOMe (50 mL x 2) and basified with 20% aq. NaOH to pH~ 10. The resulting aqueous layer was further extracted with t-BuOMe (100 mL x 3). The combined organic layers were then dried over anhy. Na2S04, filtered, and concentrated in vacuo to give a crude product, which was purified by column chromatography to give the title product (3.0 g, yield 51.7%) as yellowish oil. MS: 231.7 (M+H+, IBr)

The synthetic route of 2-Bromo-4-fluorobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; AEBI, Johannes; AMREIN, Kurt; CHEN, Wenming; HORNSPERGER, Benoit; KUHN, Bernd; LIU, Yongfu; MAERKI, Hans P.; MAYWEG, Alexander V.; MOHR, Peter; TAN, Xuefei; WANG, Zhanguo; ZHOU, Mingwei; WO2013/79452; (2013); A1;,
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Synthetic Route of 75344-77-3,Some common heterocyclic compound, 75344-77-3, name is 4-Bromo-3,5-dimethylbenzonitrile, molecular formula is C9H8BrN, 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.

Under a nitrogen atmosphere, Add 420 mg to a 250 ml three-neck round bottom reaction bottle4-bromo-3,5-dimethylbenzonitrile and 10-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-phenoxazine, Then, 120 ml of toluene, 40 ml of absolute ethanol and 40 ml of a 2 mol-liter potassium carbonate aqueous solution were sequentially added thereto, followed by stirring to dissolve. After 15 minutes of aeration, 50 mg of tetrakis(triphenylphosphine)palladium(0) catalyst was added, and after aeration for 30 minutes, it was heated to 85 C and refluxed for 24 hours. After the reaction was stopped and the reaction was stopped, the solvent of the reaction system was removed by steaming. The reaction system was extracted with a dichloromethane solvent. It was washed three times with deionized water, three times with saturated brine, and dried over anhydrous magnesium sulfate for 1 hour. Purification of the product by column chromatography, The eluent is a mixed solvent of petroleum ether and dichloromethane in a ratio of 3:1. Finally, a white solid product was obtained with a yield of 69%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-3,5-dimethylbenzonitrile, its application will become more common.

Reference:
Patent; South China University of Technology; Su Shijian; Cai Xinyi; Qiu Weidong; Qiao Zhenyang; (32 pag.)CN108530376; (2018); A;,
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Synthetic Route of 501420-63-9, 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 501420-63-9 as follows.

To a stirred suspension of NaH (16.3 g, 406 mmol, 3 eq) in anhyd THF (100 mL) at 0 0C was added dropwise a solution of 2-(3-bromo-4-fluorophenyl)acetonitrile (29 g, 135 mmol) in anhyd THF (200 mL). After stirring Ih, MeI (42.1 mL, 675 mmol, 5 eq) was added to the reaction mixture. After stirring 2h at 0 0C, the reaction was allowed to warm to room temperature, quenched carefully with H2O and extracted with EtOAc. The combined extracts were washed with brine, dried over MgSO4 and evaporated in vacuo to give 2-(3-bromo-4- fluorophenyl)-2-methylpropanenitrile (29 g, 88%). 1H NMR (400 MHz, CDCl3) delta 7.66-7.64 (m, IH), 7.44-7.40 (m, IH), 7.15 (t, J=8.4 Hz, IH), 1.72 (s, 6H).

According to the analysis of related databases, 501420-63-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EXELIXIS, INC.; BOLLU, Venkataiah; BOREN, Brant, Clayton; DALGARD, Jackline, Eve; FLATT, Brenton, T.; HAQ, Nadia; HUDSON, Sarah; MOHAN, Raju; MORRISSEY, Michael; PRATT, Benjamin; WANG, Tie-lin; WO2010/93845; (2010); A1;,
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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. 4592-94-3, name is 3-(4-Bromophenyl)-3-oxopropanenitrile, A new synthetic method of this compound is introduced below., Quality Control of 3-(4-Bromophenyl)-3-oxopropanenitrile

To a cooled (0C) and stirred solution of 3-(4-bromophenyl)-3-oxopropanenitrile (Example 230, 4.00 g, 17.85 mmol) in THF (20 mL) was added sodium hydride (60% in oil dispersion, 857 mg, 21.4 mmol). After gas evolution ceased, the mixture was warmed to rt, and isatoic anhydride (3.49 g, 17.85 mmol) was added. The reaction was heated to reflux for 16 h and then cooled to rt. The reaction was quenched and adjusted to pH 5 by slow addition of hydrochloric acid (1 N aqueous solution). The resulting white solid was collected by filtration and triturated with diethyl ether/acetone (3:1) to afford 3.5 g (60%) of desired product. 1H NMR (400 MHz, DMSOd6) delta 12.73 (br s, 1 H), 8.13 (dd, 1 H), 7.70-7.87 (m, 6 H), 7.49 (dddd, 1 H); ES-MS m/z 326.8 [M+H]+, HPLC RT (min) 2.95

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; BAYER PHARMACEUTICALS CORPORATION; WO2006/34491; (2006); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts