Tag: M.W=200-300

Related Products of 160892-07-9, These common heterocyclic compound, 160892-07-9, name is 5-Bromoisophthalonitrile, 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.

The compound D (12.77 g, 17.86 mmol) and 5-bromoisophthalonitrile (3.20 g, 15.53 mmol) were completely dissolved in 210 ml of tetrahydrofuran in a 500 ml round-bottomed flask under nitrogen atmosphere, and 2M potassium carbonate aqueous solution (105 ml) And tetrakis(triphenylphosphine) palladium (0.54 g, 0.47 mmol) was added thereto, followed by heating and stirring for 3 hours.The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 120 ml of tetrahydrofuran to obtain Compound 9 (8.42 g, yield 76%).

Statistics shows that 5-Bromoisophthalonitrile is playing an increasingly important role. we look forward to future research findings about 160892-07-9.

Reference:
Patent; LG Chem, Ltd.; Cha Yong-beom; Kim Yeon-hwan; Jeon Sang-yeong; Cho Yeon-ho; Lee Seong-jae; Han Su-jin; (53 pag.)KR2019/44973; (2019); A;,
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Reference of 70591-86-5, These common heterocyclic compound, 70591-86-5, name is 3-Bromobenzoylacetonitrile, 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.

Example IV-34 3-(3-bromophenyl)-5-isoxazolamine To a solution of 3-(3-bromophenyl)-3-oxopropanenitrile (1.12 g; 5.00 mmol; Note 1) in EtOH (20 mL) was added a solution of hydroxylamine hydrochloride (1.74 g; 25 mmol) and NaOAc (2.46 g; 30 mmol) in water (20 mL). The mixture was heated under reflux for 1 h, cooled and concentrated in vacuo. The residue was slurried in 1N NaOH and extracted with Et2O (*1). The organic layer was washed (water, brine), dried over Na2SO4 and concentrated in vacuo affording the title compound as a pale yellow solid which was used without further purification. LC/MS (method B) 2.21 min, m/z 239, 241 (Br isotopes).

The synthetic route of 70591-86-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Smithkline Beecham Corporation; US2011/124559; (2011); 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. 1835-65-0, name is 3,4,5,6-Tetrafluorophthalonitrile, This compound has unique chemical properties. The synthetic route is as follows., Safety of 3,4,5,6-Tetrafluorophthalonitrile

Referential Example 3; Synthesis of 4,5-bis(2-chloro phenylthio)-3-fluoro-6-(2,6-dimethylphenoxy)phthalocyanine; Into a four-neck flask of glass provided with a stirrer, a thermometer, a water separation tube, and a cooling tube and having an inner volume of 100 ml, 30 gr of 2-butanone, 10 gr (0.05 mol) of tetrafluorophthalonitrile, and 7.26 gr (0.125 mol) of potassium fluoride were placed and the flask was dipped in a water bath. 15.2 g (0.105 mol) of 2-chlorobenzene thiol was added to the reaction mixture with stirred at room temperature over about 40 minutes. The reaction temperature rose to the maximum of about 35° C. When the reaction was continued for additional one hour after the completion of this addition, the conversion of tetrafluorophthalonitrile reached 99.2percent. The content of the bisthiol moiety, 4,5-bis(2-chloro phenylthio)-3,6-difluorophthalonitrile, a determined by liquid chromatography, was 92.5percent. Then, 7.33 gr (0.06 mol) of 2,6-xylenol, 4.35 gr (0.075 mol) of potassium fluoride and and 6 gr of 2-butanone were added to the reaction mixture in the reaction vessel and the resultant mixture was heated to a temperature in the range of 83-86° C., and then left reacting under reflux for 30 hours. The conversion of 4,5-bis(2-chloro phenylthio)-3,6-difluorophthalonitrile after the completion of the reaction was determined by liquid chromatography, to find to be 99.8percent and the content of the target product, 4,5-bis(2-chloro phenylthio)-3-fluoro-6-(2,6-dimethylphenoxy)phthalonitrile, as determined by liquid chromatography, was 70percent. The reaction slurry was cooled to room temperature and filtered to separate a solid component. The filtrate consequently formed was separated. The resultant cake was washed with about 200 ml of chloroform. By evaporating the washing under a reduced pressure at 50° C., 18.0 g (0.0326 mol, yield: 65.2 mol percent based on tetrafluoronitrile) of 4,5-bis(2-chloro phenylthio)-3-(2,6-dimethylphenoxy)-6-fluorophthalonitrile was obtained.

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 1835-65-0.

Reference:
Patent; Hirota, Kouichi; Hashimoto, Yukihide; Masuda, Kiyoshi; Kitao, Masunori; US2005/203293; (2005); A1;,
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These common heterocyclic compound, 64695-82-5, name is 2-Bromo-4,5-difluorobenzonitrile, 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. Safety of 2-Bromo-4,5-difluorobenzonitrile

2-Bromo-4,5-difluorobenzonitrile (1.0 g, 4.59 mmol), tert-butyl (2S)-2-methylpiperazine-1-carboxylate (0.96 g, 4.82 mmol), Pd2(dba)3 (0.21 g, 0.23 mmol), XantPhos (0.27 g, 0.46 mmol) and sodium tert-butoxide (1.32 g, 13.76 mmol) were suspended in 1,4-dioxane (20 ml) (degassed with nitrogen for 5 minutes) then the reaction was heated at 100 C. for 6 h. The reaction was cooled then filtered through Celite, using DCM. The filtrate was concentrated in vacuo then the residue was partitioned between DCM (50 ml) and water (30 ml) and the organics were separated, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified via flash column chromatography using gradients of 0% to 100% EtOAc in heptane followed by 0% to 100% MeOH in EtOAc, then the fractions containing product were concentrated in vacuo to yield the title compound as a pale yellow oil which crystallized on standing (548 mg, 35%). 1H NMR (500 MHz, DMSO-d6) 8.04 (dd, J=10.4, 8.8 Hz, 1H), 7.32 (dd, J=12.7, 7.2 Hz, 1H), 4.24 (s, 1H), 3.84 (d, J=13.2 Hz, 1H), 3.32 (d, J=2.1 Hz, 2H), 3.16 (t, J=11.4 Hz, 1H), 2.90 (dd, J=12.1, 3.7 Hz, 1H), 2.78 (td, J=11.9, 3.4 Hz, 1H), 1.42 (s, 9H), 1.27 (d, J=6.7 Hz, 3H). LCMS Method 2-Tr=1.28 min (ES+) (M+H+) 360.1

The synthetic route of 2-Bromo-4,5-difluorobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Navitor Pharmaceuticals, Inc.; O’Neill, David John; Saiah, Eddine; Kang, Seong Woo Anthony; Brearley, Andrew; Bentley, Jonathan; (519 pag.)US2018/127370; (2018); A1;,
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Related Products of 6575-12-8,Some common heterocyclic compound, 6575-12-8, name is 2,6-Dibromobenzonitrile, molecular formula is C7H3Br2N, 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.

42b) 2-(2,6-Dibromophenyl)-3-{[4-(1,1-dimethylethyl)phenyl]methyl}-6-hydroxy-4(3H)-pyrimidinone; A 1 M solution of dimethylaluminium chloride in hexane (2.20 mL, 2.20 mmol) was added to a stirred mixture of 4-tert-butylbenzylamine (0.326 g, 2.00 mmol), 2,6-dibromobenzonitrile (0.587 g, 2.25 mmol) and toluene (6 mL) at room temperature. The mixture was stirred in a microwave reactor at 160 C. for 0.5 h, then cooled and the solvent removed under reduced pressure. Diethyl malonate (1.28 g, 8.00 mmol), 2-methoxyethanol (12 mL) and 4.37 M sodium methoxide in methanol (1.83 mL, 8.00 mmol) were added and the mixture refluxed under nitrogen for 18 h. After cooling, the mixture was poured into water (150 mL), washed with ether, acidified to pH 1 with 6 M aqueous hydrochloric acid, and extracted with ethyl acetate. The extracts were washed with water and brine, dried (MgSO4) and evaporated under reduced pressure. The residue was triturated with ether and the solid collected, washed with ether and dried to give the title compound (0.361 g, 37%) as a cream solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 1.23 (s, 9 H) 4.86 (s, 2 H) 5.59 (s, 1 H) 6.74-6.80 (m, 2 H) 7.17-7.22 (m, 2 H) 7.43 (t, J=8.08 Hz, 1 H) 7.76 (d, J=8.08 Hz, 2 H) 11.86 (s, 1 H).

The synthetic route of 6575-12-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shaw, Antony N.; Duffy, Kevin J.; Tedesco, Rosanna; Wiggall, Kenneth; US2008/171756; (2008); A1;,
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68385-95-5, name is 2-Amino-3,5-dibromobenzonitrile, 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. category: nitriles-buliding-blocks

To a solution of 2,4-dibromo-6-cyanoaniline (200.00 g, 724.82 mmol) and DMAP(17.71 g, 144.96 mmol) in DCM (3 L), Boc2O (474.58 g, 2.17 mol) was added and thereaction mixture was stirred at 45 C for 4 h. The crude mixture was successively washed with saturated NaHCO3 (2 x 1 L) and brine (2 x 1 L), dried over MgSO4, filtered and concentrated under vacuum to give 323 g of intermediate 1 (56% yield, yellow solid, 86% purity evaluated by LC/MS). The product was used in the next stepwithout any further purification.

The synthetic route of 68385-95-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; STANSFIELD, Ian; QUEROLLE, Olivier Alexis Georges; PONCELET, Virginie Sophie; GROSS, Gerhard Max; JACOBY, Edgar; MEERPOEL, Lieven; KULAGOWSKI, Janusz Jozef; MACLEOD, Calum; MANN, Samuel Edward; GREEN, Simon Richard; HYND, George; (477 pag.)WO2017/125530; (2017); A1;,
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Application of 134604-07-2, These common heterocyclic compound, 134604-07-2, name is 1-Cyano-2-bromo-5-nitrobenzene, 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.

Step 1 2-Cyano-4′-methyl-4-nitrobiphenyl To a solution of p-tolyltrimethyltin (389 mg, 1.525 mmol) in dry toluene (5 mL) under N2 was added 2-bromo-5-nitro-benzonitrile (276 mg, 1.22 mmol) and Pd(PPh3)4 (176 mg; 10 mol %). The reaction was stirred at reflux under N2 for 24 hours and then cooled to room temperature. The mixture was diluted with EtOAc and the solid was removed by filtration through a pad of celite. The filtrate was concentrated in vacuo and the residue was purified by flash chromatography on a silica column eluding with Hex/EtOAc (10:1) to afford 214 mg (74%) of the titled compound as a slightly yellow solid. 1 H-NMR: (300 MHz, CDCl3) delta 2.42 (s, 3H), 7.32 (d, 2H), 7.48 (d, 2H), 7.69 (d, 1H), 8.45 (dd, 1H), 8.61 (s, 1H).

Statistics shows that 1-Cyano-2-bromo-5-nitrobenzene is playing an increasingly important role. we look forward to future research findings about 134604-07-2.

Reference:
Patent; Merck & Co., Inc.; US5240928; (1993); A;,
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Application of 867366-91-4, A common heterocyclic compound, 867366-91-4, name is 3-Bromo-5-methoxybenzonitrile, molecular formula is C8H6BrNO, 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.

Example 43 2-[(4-Fluoro-benzenesulfonyl)-methyl-amino]-N-(5-methoxy-4′-trifluoromethyl-biphenyl-3- ylmethyl)-acetamide A solution of 4,4,5,5-tetramethyl-2-(4-trifluoromethyl-phenyl)-[l,3,2]dioxaborolane(1.00 g, 3.68 mmol), 3-bromo-5-methoxy-benzonitrile (0.78 g, 3.68 mmol) and potassium carbonate (0.51 g, 3.68 mmol) in DMF (5 mL) at 25C was purged with nitrogen gas and evacuated three times. The solution was then treated with teira 3s(triphenylphosphine)palladium(0) (212 mg, 184 muiotaetaomicron) and then sealed and heated to 120C for 14 h. The reaction mixture was cooled to 25 C, unsealed and poured into water. The aqueous phase was extracted three times with ethyl acetate. The combined organic layers were washed with brine and dried over magnesium sulfate. Filtration followed by concentration in vacuo gave a brown solid. Flash chromatography (80/20 hexanes/ethyl acetate) afforded 5-methoxy- 4′-trifluoromethyl-biphenyl-3-carbonitrile (0.70 g, 69%) as a white solid.

The synthetic route of 867366-91-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BROTHERTON-PLEISS, Christine E.; CHEN, Huifen; CHEN, Shaoqing; CHEN, Zhi; ERICKSON, Shawn David; ESTRADA, Anthony; KIM, Kyungjin; LI, Hongju; LOVEY, Allen John; LYSSIKATOS, Joseph P.; QIAN, Yimin; SO, Sung-Sau; WOVKULICH, Peter Michael; YI, Lin; WO2014/49047; (2014); 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. 1813-33-8, name is 2-Chloro-4-(trifluoromethyl)benzonitrile, A new synthetic method of this compound is introduced below., Quality Control of 2-Chloro-4-(trifluoromethyl)benzonitrile

Dissolve 2-chloro-4-trifluoromethylbenzonitrile (405 mg, 1.97 mmol) in anhydrous toluene (7 mL) and cool in a dry ice/ethanol bath. Add diisobutylaluminum EPO hydride (DIBAL) (3.94 niL, 3.94 mmol, 1.0 M in toluene) slowly. Stir 30 min. Warm to room temperature, add acetic acid (2 mL) and water (10 rnL) and stir for 2 hours. Extract the aqueous layer with ethyl acetate twice. Wash the organic layer with potassium sodium tartrate solution (Rochelle salt) twice. Dry (magnesium sulfate), filter, and concentrate to give a residue. Chromatograph the residue on silica gel eluting with a gradient of 100:0 to 1:1 hexanes:dichloromethane to give 2-chloro-4- trifluoromethylbenzaldehyde (123 mg, 30%). 1H NMR (400 MHz, CDCl3) delta 10.52 (s, IH), 8.05 (d, IH5 J = 8.0 Hz), 7.75 (s, IH), 7.66 (d, IH, J = 8.0 Hz).

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; ELI LILLY AND COMPANY; WO2006/44454; (2006); A1;,
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Adding a certain compound to certain chemical reactions, such as: 1953-99-7, name is 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, 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 1953-99-7, Application In Synthesis of 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile

To a boiling solution of lithium 1-hexanolate in 1-hexanol, prepared via dissolving 0.1 g oflithium in 20 ml of anhydrous 1-hexanol, added compound 3 (0.7 g, 2 mmol) and compound5 (0.53, 2 mmol). After 5 h, the reaction mixture was cooled and mixed with 50 ml of acetoneand 5 ml of acetic acid. Then reaction mixture was concentrated at rota evaporator, purifiedby silica gel column chromatography usingDCM:CH3OH(20:1) as an eluent to obtain an oilybluish green compound as a major fraction, To this compound Zn(OAc)2·2H2O (0.13 g, 0.6mmol), and 20 ml of DMF added and heated at reflux for 1 h. After cooling, to the reactionmixturewas added 100ml of water and 100ml of chloroform. The organic layer was separated,washed with 100ml of water, then reaction mixture was concentrated at rota evaporator, purifiedby silica gel column chromatography using DCM:CH3OH (20:1) as an eluent to obtainoily bluish green compound 6 (0.368 g, 52.5percent). IR (KBr tablet) numax/cm?1: 3018, 2956, 2857,1597, 1492, 1265, 1214, 1154, 1092, 971, 745. 54H18Cl8F6N84Zn; Calculated, percent: 49.67; H1.39; N 8.58; O 4.9, Found, percent: 49.89; H 1.42; N 8.48; O 4.93. UV-Vis: nm (log epsilon): in CHCl3;660(102),715(142),815(45). MALDI-TOF-MS: m/z calcd for 54H18Cl8F6N84Zn, 1303.81;found 1304.74 [M + H+]+.

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:
Article; Jeong, Jaemyeng; Kumar, Rangaraju Satish; Kim, Ick Jin; Son, Young-A; Molecular Crystals and Liquid Crystals; vol. 644; 1; (2017); p. 249 – 256;,
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