Month: June 2021

Related Products of 179898-34-1,Some common heterocyclic compound, 179898-34-1, name is 3-Bromo-5-fluorobenzonitrile, molecular formula is C7H3BrFN, 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.

Intermediate T5: 3-fluoro-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile A mixture of 3-bromo-5-fluorobenzonitrile (0.300 g, 1.5 mmol), bis(pinacolato) diboron (0.762 g, 3 mmol), KOAc (0.589 g, 6.0 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.110 g, 0.15 mmol) in dioxane (15 mL) was stirred at 90 C. for 2 h. The solvent was removed and the residue was purified by flash chromatography on Biotage silica 50 g cartridge (cyclohexane to cyclohexane_EtOAc=70:30) to afford title compound (0.360 g, 1.46 mmol, 97% yield). 1H NMR (400 MHz, DMSO-d6) delta ppm 7.98-8.03 (m, 1H), 7.81-7.85 (m, 1H), 7.68-7.73 (M, 1H), 1.33 (s, 12H).

The synthetic route of 179898-34-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHIESI FARMACEUTICI S.P.A.; BIAGETTI, Matteo; ACCETTA, Alessandro; CAPELLI, Anna Maria; GUALA, Matilde; RETINI, Michele; US2015/361100; (2015); A1;,
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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, Safety of 4-(Trifluoromethyl)benzonitrile

-Trifluoromethyl-thiobenzamide A solution of oc, a, [A-TRIFLUORO-P-TOLUNITRILE] (603.5 g, 3.53 mol) in dry DMF (2 L) under N2 was heated at [70C] and the Thioacetamide (505 g, 1.9 eq. ) was added. The reaction mixture was treated with HCI gas before 15 minutes and was stirred at [95C] for 6 hours. This treatment was operated 3 times and the mixture was stirred at rt for 24 hours. After cooling at [0C,] water was added and the residue was extracted with diethyl ether (4*1 L). The organic layer was washed with water (3*1 L), dried over [NA2SO4] and then evaporated off. The brownish powder was washed with pentane (3 L) to give the title compound (530.3 g, 2.59 mol) as brown solid in a 73% yield. GC/MS: [M+ C8H6F3NS] 205

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:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2004/785; (2003); 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. 1009-35-4, name is 4-Fluoro-3-nitrobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H3FN2O2

To a solution of methyl 4-aminocyclohexane carboxylate hydrochloride (1.5 g, 7.74 mmol) and 4-fluoro-3-nitrobenzonitrile (1.28 g, 7.74 mmol) in acetonitrile (50 ml) was added N,N-diisopropylethylamine (2.69 ml, 15.49 mmol) at ambient temperature. The resulting reaction mixture was stirred for 18 hours at room temperature. Acetonitrile was removed under reduced pressure and the crude solid was dissolved in dichloromethane and the dichloromethane layer was washed with water, dried over magnesium sulfate, filtered and then concentrated under reduced pressure. The crude solid product was washed with cold methanol and used in the next step without any further purification. Yield 1.8 g.77percent MS (ESI) m/z for C15H17N3O4 = 303.12 (calcd) 304.2 ([M + H]+, found)

According to the analysis of related databases, 1009-35-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; OSLO UNIVERSITY HOSPITAL HF; FORSCHUNGSVERBUND BERLIN E.V.; UNIVERSITY OF OULU; KRAUSS, Stefan; NAZARE, Marc; ANUMALA, Upendra Rao; LEHTIO, Lari; WAALER, Jo; HOLSWORTH, Dan; WEGERT, Anita; LEENDERS, Ruben Gerardus George; (99 pag.)WO2018/118868; (2018); A1;,
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Application of 6621-59-6, 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. 6621-59-6, name is 6-Bromohexanenitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A solution of the corresponding precursor (4-chlorobutyronitrile for compounds 1, 5-chlorovaleronitrile for compounds 3 and 6-bromohexanenitrile for compounds 6) (2.5 mmol) in dimethylformamide (1 mL) was added during 1.5 h to a mixture of the arylamine (2.5 mmol), Cs2CO3(2.5 mmol) and KI (5 mmol) in dimethylformamide (2.5mL). The mixture was stirred at the indicated temperature and time. After completion of the reaction, as indicated by TLC, the mixture was treated with ethyl ether (50 mL) and water (10 mL). The aqueous phase was separated and extracted with ethyl ether (30 mL). The combined organic layers were dried over anhydrous sodium sulfate and filtered. The solvent was evaporated in vacuo. The crude product was purified by column chromatography (silica gel, hexane:DCM).

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

Reference:
Article; Diaz, Jimena E.; Mollo, Maria C.; Orelli, Liliana R.; Beilstein Journal of Organic Chemistry; vol. 12; (2016); p. 2026 – 2031;,
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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. 1572-52-7, name is 2-Methylenepentanedinitrile, This compound has unique chemical properties. The synthetic route is as follows., name: 2-Methylenepentanedinitrile

a. 426 g (4 moles) of 2-methyleneglutaronitrile, 264 g (4 moles) of cyclopentadiene, 4 g of hydroquinone and 500 ml of benzene are heated in a pressure autoclave at 160 and under a maximum pressure of 3 bars, with stirring, for 10 hours. The mixture obtained after cooling is concentrated in vacuo (ca. 12 Torr), the residue twice extracted with 1.5 liters of petroleum ether each time and then extracted in high vacuum. The crude product is obtained as colourless oil, B.P. 115-128/0.03 Torr, which is dissolved in 300 ml of ethanol. On storage of this solution in a refrigerator overnight, there crystallises 2-exo-cyano-5-norbornene-2-endo-propionitrile, M.P. 40-42.

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 1572-52-7.

Reference:
Patent; Ciba-Geigy Corporation; US4015007; (1977); A;,
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Related Products of 766-84-7,Some common heterocyclic compound, 766-84-7, name is 3-Chlorobenzonitrile, molecular formula is C7H4ClN, 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.

Preparation of N-(2-butyryl-4-chlorophenyl)trifluoromethanesulfonamide (Formula 29A) a) To a stirred solution of 3-chlorobenzonitrile (2.0g, 14.54 mmol) and n-propylmagnesium chloride (2M in Et2O) (8.0 mL, 15.99 mmol) in THF (40 mL) was added CuCl (29 mg, 0.29 mmol), and the mixture was refluxed for 30 minutes. After cooling to RT, cold 1N HCl (10 mL) was added cautiously, the THF removed under reduced pressure, further 1N HCl (30 mL) added and the reaction heated at 90 C. for 1 hour. To the cooled reaction mixture was added water (20 mL) and CH2Cl2 (50 mL), the phases separated, and the aqueous phase again extracted with CH2Cl2. The combined organics were washed with water, dried over MgSO4 and the solvent evaporated under vacuum. The residue was filtered through a pad of silica (eluting with CH2Cl2) to afford 1-(3-chlorophenyl)butan-1-one 26A (3.14 g, 97%), as a yellow liquid.

The synthetic route of 766-84-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Meyer, Adam Gerhard; Winzenberg, Kevin Norman; Sawutz, David G.; Liepa, Andris Juris; US2006/63841; (2006); A1;,
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Some common heterocyclic compound, 4592-94-3, name is 3-(4-Bromophenyl)-3-oxopropanenitrile, molecular formula is C9H6BrNO, 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. Computed Properties of C9H6BrNO

General procedure: To a solution of catalyst 4 (0.01mmol), 3,5-(NO2)2C6H3CO2H (0.02mmol), and alpha,beta-unsaturated aldehyde 2 (0.10mmol) in toluene (1.0mL) was added alpha-cyanoketones 1 (0.15mmol) at 0C. The resulting solution was then stirred for 48h. After complete consumption of the aldehyde (as monitored by TLC), the reaction mixture was evaporated and then loaded onto silica gel (ethyl acetate/petroleumether=1:10 to 1:7) and the products 3a-n were obtained by column chromatography. 4.2.1 (4S)-6-(4-Bromophenyl)-2-hydroxy-4-phenyl-3,4-dihydro-2H-pyran-5-carbonitrile 3a The title compound was obtained according to the general procedure (87% yield) as a mixture of two diastereoisomers (major and minor). Yellow solid; [alpha]D30 = +22.6 (c 1.30, CHCl3); mp = 146-147 C; 1H NMR (400 MHz, CDCl3): delta 7.67 (d, J = 8.8 Hz, 2H; both diastereoisomers), 7.56 (d, J = 8.8 Hz, 2H; both diastereoisomers), 7.41-7.37 (m, 2H; both diastereoisomers), 7.32-7.29 (m, 3H; both diastereoisomers), 5.63 (s, 1H; major), 5.56 (s, 1H; minor), 3.94 (dd, J = 9.6, 6.4 Hz, 1H; major), 3.88 (dd, J = 10.0, 6.8 Hz, 1H; minor), 3.62 (s, 1H), 2.51-2.45 (m, 1H; minor), 2.29-2.23 (m, 1H; major), 2.09-2.03 (m, 1H; both diastereoisomers); 13C NMR (100 MHz, CDCl3): delta 162.1, 140.9, 132.0, 131.7, 129.8, 129.7, 129.2, 129.1, 127.9, 127.7, 127.5, 125.3, 119.0, 96.0, 92.6, 88.2, 40.3, 37.5, 36.6, 35.4 ppm; (additional peaks are observed due to diastereoisomers). IR (KBr): nu 3377.5, 2207.1, 1608.5, 1588.4, 1488.0, 1454.0, 1145.0, 1010.7, 954.9, 867.9, 829.8, 728.3, 700.9 cm-1; d.r.: trans/cis = 3.63/1; ESI-MS (m/z): 354.1 (M-H)-; HRMS(ESI): calcd for ([C18H14NO2BrNa+]): 378.0100. Found: 378.0086; enantiomeric excess: 96%, determined by HPLC (Chiralcel OD-H column, hexane/i-PrOH 80:20, flow rate 0.7 mL/min; lambda = 254 nm, tmajor = 17.5 min, tminor = 11.0 min).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4592-94-3, its application will become more common.

Reference:
Article; Niu, Zhiqiang; He, Xinwei; Shang, Yongjia; Tetrahedron Asymmetry; vol. 25; 10-11; (2014); p. 796 – 801;,
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Electric Literature of 1885-29-6, A common heterocyclic compound, 1885-29-6, name is 2-Aminobenzonitrile, molecular formula is C7H6N2, 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.

A mixture of 2-aminobenzonitrile (5 g, 42.3 mmol) and NBS (16.57g, 93.1 mmol, 2.2 equiv) was refluxed in MeCN (80 mL) for 3 h. After cooling, the precipitate formed was filtered, washed with H2O (3 × 60 mL), and dried in a vacuum drying oven (desiccator cabinet). Recrystallization from propan-2-ol gave 1 as a brown solid; yield: 8.9 g (77%); mp 158 C (Lit.14 mp 156 C). 1H NMR (200 MHz, CDCl3): delta = 4.91 (s, 2 H, NH2), 7.47 (d, J = 2.1Hz, 1 H, H-4), 7.71 (d, J = 2.1 Hz, 1 H, H-6). 13C NMR (50 MHz, CDCl3): delta = 97.9, 108.2, 109.7, 115.6, 133.6,139.4, 146.2.

The synthetic route of 1885-29-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kabri, Youssef; Crozet, Maxime D.; Redon, Sebastien; Vanelle, Patrice; Synthesis; vol. 46; 12; (2014); p. 1613 – 1620;,
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Related Products of 5332-06-9, These common heterocyclic compound, 5332-06-9, name is 4-Bromobutanenitrile, 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.

(trans) 1-(1 H-benzimidazol-2-ylmethyl)-2,3,3a,4,5,9b-hexahydro-1 H-pyrrolo[3,2- /?]quinoline (0.032 g, 0.11 mmol), potassium carbonate (0.075 g, 0.55 mmol), 4- bromobutanenitrile (0.024 g, 0.16 mmol), and potassium iodide (5 mg) in 3 ml_ of N,N-dimethyIformamide were heated to 80 2C in a sealed tube for 16 hours. The mixture was allowed to cool to room temperature and quenched with 5 ml_ of water. The mixture was extracted 3 times with 5 mL of dichloromethane and the combined organic layers concentrated. The residue was dissolved in 20 mL of a 2M ammonia solution in methanol and hydrogenated under 40 psi of hydrogen for 18 hours, with 30 mg of raney nickel as catalyst. The catalyst was filtered off over celite and the filtrate concentrated. The residue was purified by silica chromatography eluting with a 0% to 10% gradient of aqueous ammonia in acetonitrile to yield 29 mg (70%) of (trans) 4-[2-(2,3,3a,4,5,9b-hexahydro-1 H-pyrrolo[3,2-/7]quinolin-1 -ylmethyl)-1 H- benzimidazol-1-yl]-1 -butanamine. 1 H NMR (400 MHz, METHANOL-D4) delta ppm 1.1 (m, 2 H), 1.4 (m, 2 H), 1.7 (m, 2 H), 1.8 (m, 1 H), 2.1 (m, 1 H), 2.4 (m, 1 H), 2.5 (t, J=7.4 Hz, 2 H), 2.7 (m, 1 H), 2.8 (m, 2 H), 2.9 (m, 1 H), 3.6 (d, J=8.6 Hz, 1 H), 3.6 (d, J=13.6 Hz, 1 H), 3.7 (m, 1 H), 3.8 (m, 1 H), 4.7 (d, J=13.6 Hz, 1 H), 7.2 (m, 2 H), 7.4 (m, 2 H), 7.6 (m, 1 H), 7.7 (d, J=7.9 Hz, 1 H), 8.4 (d, J=6.4 Hz, 1 H); MS m/z376(M+1).

The synthetic route of 5332-06-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/96444; (2006); A2;,
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Electric Literature of 90110-98-8,Some common heterocyclic compound, 90110-98-8, name is 3-Bromo-4-(hydroxymethyl)benzonitrile, molecular formula is C8H6BrNO, 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.

LiAlH4 (34.0 mmol; 34.0 mL of a 1.0 M solution in THF) was cooled to 0 C using an ice bath then treated with MeOH (102 mmol; 26.4 mL of a 3.86 M solution in THF) dropwise over 5 min. The product of Part 3C (0.900 g, 4.24 mmol) was then added and the resulting solution warmed slowly to ambient temperature as the ice bath melted. After 16 h total reaction time, the solution was diluted with H2O (9.0 mL) and the resulting suspension filtered through a scintered glass funnel of medium porosity. The solids were exhaustively washed with H2O and Et2O then transferred to a separatory funnel and split. The aqueous layer was further washed with Et2O and EtOAc and the combined organic layers dried over Na2SO4, filtered and concentrated in vacuo to a yellow solid (0.591 g), which was used without further purification in the subsequent reaction.

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

Reference:
Patent; LANTHEUS MEDICAL IMAGING, INC.; RADEKE, Heike, S.; CESATI, Richard, R.; PUROHIT, Ajay; HARRIS, Thomas, D.; ROBINSON, Simon, P.; YU, Ming; CASEBIER, David, S.; HU, Carol, Hui; BROEKEMA, Matthias; ONTHANK, David, C.; WO2013/36869; (2013); A2;,
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