Tag: M.W=100-200

Application of 68119-31-3,Some common heterocyclic compound, 68119-31-3, name is 2-(2,2-Difluorobenzo[d][1,3]dioxol-5-yl)acetonitrile, molecular formula is C9H5F2NO2, 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 e: 1-(2,2-Difluoro-benzo[1,3]dioxol-5-yl)-cyclopropanecarbonitrileSodium hydroxide (50% aqueous solution, 10 mL) was slowly added to a mixture of crude (2,2-difluoro-benzo[1,3]dioxol-5-yl)-acetonitrile, benzyltriethylammonium chloride (3.00 g, 15.3 mmol), and 1-bromo-2-chloroethane (4.9 g, 38 mmol) at 70 C. The mixture was stirred overnight at 70 C. before the reaction mixture was diluted with water (30 mL) and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate and evaporated to dryness to give crude 1-(2,2-difluoro-benzo[1,3]dioxol-5-yl)-cyclopropanecarbonitrile, which was used directly in the next step.

The synthetic route of 68119-31-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ruah, Sara Hadida; Miller, Mark; Zhou, Jinglan; Bear, Brian; US2009/221597; (2009); A1;,
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Related Products of 69395-13-7, 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. 69395-13-7, name is 4-(2-Hydroxyethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

Reference Example 76 4-Cyanophenylacetic acid A catalytic amount of ruthenium chloride (28 mg) and sodium periodate (5.80 g) were added to a carbon tetrachloride-acetonitrile-water (2:2:3) solvent solution (20 ml) of 4-(2-hydroxyethyl)benzonitrile (1.00 g), followed by stirring overnight at room temperature. The reaction solution was extracted with dichloromethane and dried over sodium sulfate to obtain the title compound (755 mg) as a colorless oil. 1H-NMR (400 MHz, CDCl3) delta: 3.73 (2H, s), 7.40 (2H, d, J=8.3 Hz), 7.63 (2H, d, J=8.3 Hz).

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

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1612204; (2006); A1;,
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Application of 51762-67-5, A common heterocyclic compound, 51762-67-5, name is 3-Nitrophthalonitrile, molecular formula is C8H3N3O2, 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.

3-nitrophthalonitrile (0.99 g, 5.90 mmol) was dissolved in 15.0 ml DMF under argon atmosphere and 3,4-dimethoxythiophenol (1.00 g, 5.90 mmol) was added at room temperature. After stirring for 30 min at room temperature, finely ground anhydrous potassium carbonate (3.94 g, 28.4 mmol) was added portion wise for over 1 h and the reaction mixture was stirred at room temperature for 24 h. Then the mixture was poured into 100.0 ml ice water, and the precipitate was filtered off, washed with water and methanol, and then dried. The crude product was recrystallized from ethanol. Finally the pure product was dried in vacuum. Yield: 3.12 g (90%). FT-IR (cm-1) (KBr): 3070, 3004 (Ar-CH), 2960, 2934, 2840 (CH), 2230 (C?N), 1583, 1567, 1505 (C=C), 1461, 1439, 1417, 1401, 1328, 1259 (C-O-C), 765 (C-S-C). 1H NMR (CDCl3): delta = 7.65-7.06 (6H, m, Ar-H), 3.92 (3H, s, C-H), 3.82 (3H, s, C-H). Calcd for C16H12N2O2S: C, 64.90; H, 4.10; N, 9.45; S, 10.80; Found: C, 64.85; H, 4.14; N, 9.52; S, 10.85. MS (GC-MS) m/z: Calc.: 296.35, Found: 296 [M]+.

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; Arican, Duygu; Arici, Muersel; Ugur, Ahmet Luetfi; Erdo?mu?, Ali; Koca, Atif; Electrochimica Acta; vol. 106; (2013); p. 541 – 555;,
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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 3672-47-7 as follows. Quality Control of 3-(4-Methoxyphenyl)-3-oxopropanenitrile

General procedure: To a 0.5-2.0ml vial with 1 mmol ketone (1 eq) issolved in 2-pentanol (1.66 M) was added 1.1 eq of aromatic aldehyde and catalytic piperidine (0.08 eq), stirring vigorously. After heating under muWave for 15min at 120 C, the reaction was cooled to r.t. and precipitate was vacuum filtered and washed with minimal, cold hexanes. After drying under vacuum, solid was analyzed via NMR, IR, and mp.

According to the analysis of related databases, 3672-47-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Deshpande, Shyam J.; Leger, Paul R.; Sieck, Stephen R.; Tetrahedron Letters; vol. 53; 14; (2012); p. 1772 – 1775;,
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Related Products of 6393-40-4, 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 6393-40-4 as follows.

1g (6.1mmol) 4-Amino-3-nitrobenzonitrile was dissolved in 50ml ethanol and was subjected to hydrogenation using 35 psi of H2 and 10% Pd.C until the end of H2 uptake. The catalyst was filtered on a bed of Celite, washed with ethanol and concentrated in vacuo. Powder residue was used for the subsequent steps without crystallization. Yield: 88% (0.72g). Mp: 144-146C.14

According to the analysis of related databases, 6393-40-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Karaaslan, Cigdem; Kaiser, Marcel; Brun, Reto; Goeker, Hakan; Bioorganic and Medicinal Chemistry; vol. 24; 18; (2016); p. 4038 – 4044;,
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These common heterocyclic compound, 94087-40-8, name is 3-Chloro-2-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. COA of Formula: C7H3ClFN

General procedure: Into an oven-dried flask equipped with a magnetic stir bar was added aryl fluoride (1.00 g, 1.0 eq.), Na2S (1.1 eq.) and DMF (5 mL) under argon. The reaction mixture was stirred at room temperature for 1 h. Then 1 M NaOH (50 mL) was added and was washed with CH2Cl2 (2 x 25 mL). The aqueous layer was acidified to pH ~ 1-2 with 6 N HCl and extracted with CH2Cl2 (2 x 50 mL). The combined organic layer was washed with brine (50 mL), dried over MgSO4, filtered and concentrated under reduced pressure to provide a crude residue. To the residue was added 10% HCl (40 mL) and cooled with an ice-water bath. Then zinc dust (4 g) was added and the mixture was stirred for 1 h. Then EtOAc (100 mL) was added and the mixture was stirred for an additional 30 minutes. The organic layer was separated and washed with water (40 mL) and brine (40 mL), dried over MgSO4, filtered and concentrated to provide the desired product with satisfactory purity.

The synthetic route of 3-Chloro-2-fluorobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Taldone, Tony; Patel, Pallav D.; Patel, Hardik J.; Chiosis, Gabriela; Tetrahedron Letters; vol. 53; 20; (2012); p. 2548 – 2551;,
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Application of 115279-73-7, 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 115279-73-7 as follows.

To a solution of 4-hydroxy-3-methoxy-benzoic acid (90.0 mg; 0.54 mmol) in DCM (1.8 mL) were added few drops of DMF. Oxalyl chloride (180 uL; 2.12 mmol) was added dropwise to this solution, which then was stirred at room temperature for 16 hours. The solvent was evaporated under vacuum and the resulting yellow oil was dissolved in DCM (5.52 mL). This solution was added dropwise to a stirred mixture of l-(4-amino-phenyl)-cyclopentanecarbonitrile (100 mg; 0.54 mmol), prepared as in 3(B), and triethylamine (150 uL; 1.07 mmol) in DCM (4.6 mL). After stirring at room temperature for 3 hours, the solvent was evaporated under vacuum. The product was purified by preparative HPLC (Method Q), to yield the titled compound as a yellow oil (20.0 mg; 11% yield).1H NMR (300 MHz, CDC13) delta(ppm): 7.83 (br. s., 1 H), 7.64 (m, 2 H), 7.53 (d, 1 H), 7.43-7.50 (m, 2 H), 7.34 (dd, 1 H), 7.00 (d, 1 H), 3.99 (s, 3 H), 2.40-2.56 (m, 2 H), 1.84-2.17 (m, 6 H). LCMS (RT): 2.76 min (Method H); MS (ES+) gave m/z: 337.1 (MH+).

According to the analysis of related databases, 115279-73-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ADDEX PHARMA SA; WO2008/117175; (2008); A2;,
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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. 26391-06-0, name is 2-Cyano-N,N-diethylacetamide, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 2-Cyano-N,N-diethylacetamide

A mixture of 3, 4-dihydroxy-5-Nitrobenzaldehyde(70 g; 382 mmole) , N, N- Diethylcyanoacetamide (107 g; 764 mmole) , piperidine (56.6ml; 573 mmole) , and acetic acid (32.8 ml; 573 mmole) in isopropanol (700 ml) is heated at reflux during approximately 3 hours. The resulting dissolution is cooled to room temperature and the resulting precipitate is kept in stirring at this temperature overnight. Finally, it is cooled at 0-50C, filtered off and washed with isopropanol (140 ml) . The resulting product is dried at 400C in a vacuum oven to provide 119 g (79.7 % yield) of an orange solid (m.p.= 152-4C; HPLC purity= 98.0 % (Z-isomer= 0.94 %) ) .IR (cm”1) : 3190, 3038, 2975, 2828, 2723, 2547, 2201, 1631, 1607, 1542, 1480, 1439, 1387, 1357, 1318, 1265, 1221, 1187, 1176, 1156, 1074, 1018, 948, 866, 834, 802, 782, 681, 638, 607, 562.1H-NMR (500 MHz, CD3OD): 7.94 (d, J= 2.4 Hz, IH); 7.65 (d, J= 2.4 Hz, IH) ; 7.47 (s, IH) ; 3.56 (q, J= 6.6 Hz; 4H) ; 3.35-3.16 (m, 4H); 1.84-1.80 (m, 4H); 1.74-1.71 (m, 2H); 1.29 (t, J= 6.6 Hz, 6H) .Analysis. Calculated for Ci4H14N3O5-C5H12N: C, 58.45; H, 6.17; N, 14.35. Found: C, 58.19; H, 6.52; N, 14.27.

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 26391-06-0.

Reference:
Patent; QUIMICA SINTETICA, S. A.; WO2008/98960; (2008); 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. 115279-57-7, name is 2-(4-Aminophenyl)-2-methylpropanenitrile, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C10H12N2

A mixture of compound 3 (6.75g, 0.0215mol) and 2-(4-aminophenyl)-2-methylpropanenitrile (compound 4, 3.72g, 0.0233mol) in 2-propanol (25ml) was heated at reflux for 30min. The precipitated solid was collected and dried to give ethyl 6-bromo-4-(4-(2-cyanopropan-2-yl)phenylamino)quinoline-3-carboxylate (compound 5, 8.35g, 88.9%) as a bright yellow solid.

According to the analysis of related databases, 115279-57-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ADVENCHEN PHARMACEUTICALS, LLC; GUOQING, Paul, Chen; CHANGREN, Yan; MONICA, Chen; (33 pag.)WO2017/11363; (2017); A1;,
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Related Products of 134450-56-9,Some common heterocyclic compound, 134450-56-9, name is 4,5-Difluorophthalonitrile, molecular formula is C8H2F2N2, 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.

Difluorophthalonitrile (30 g, 183 mmol) was added to 1-chloronaphthalene (150 ml) in which BCl3 (14 g, 120 mmol) was dissolved, and the mixture was heated to reflux under a nitrogen atmosphere. Afier cooling, the mixture was separated and purified by silica chromatography, and then a product was purified by sublimation and purification to obtain F6-SubPc-Cl (11 g, yield 34%).

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

Reference:
Patent; SONY SEMICONDUCTOR SOLUTIONS CORPORATION; OBANA, Yoshiaki; NEGISHI, Yuki; HASEGAWA, Yuta; TAKEMURA, Ichiro; ENOKI, Osamu; MOGI, Hideaki; MATSUZAWA, Nobuyuki; (67 pag.)US2017/54089; (2017); A1;,
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