Month: July 2021

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. 4549-33-1, name is 1,9-Dibromononane, This compound has unique chemical properties. The synthetic route is as follows., Safety of 1,9-Dibromononane

Take a 50 mL flask and install a reflux condenser.Add 2.0 mL (12.56 mmol) of 2,3,3-trimethyl-3H-indole,2.55mL1,9-dibromodecane (12.56 mmol) and 20 mL of tetrahydrofuran,Heating under reflux for 24 hours;Stop heating and allow the reaction system to cool to room temperature;1534 mg (12.56 mmol) was sequentially added to the above system.4-dimethylaminopyridine and 2.1 g (12.56 mmol) of 5-nitrosalicylaldehyde,Continue the reaction for another 5 minutes and spin dry the solvent.The product was purified by silica gel column chromatography (eluent petroleum ether / ethyl acetate).A yellow solid was obtained in an amount of 3.03 g, yield 47%.

According to the analysis of related databases, 4549-33-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Qingdao University of Science and Technology; Deng Yawen; Xie Congxia; Wu Zhongtao; Zhang Lei; (6 pag.)CN110041341; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

399-94-0, name is 1-Bromo-2,5-difluorobenzene, belongs to bromides-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. Product Details of 399-94-0

Under nitrogen, 2,5-difluorobromobenzene (15.05 g, 78 mmol) was dissolved in dry toluene (50 mL)(66 mL, 1.3 mol / L) in an isopropylmagnesium chloride / lithium chloride solution was added dropwise to the temperature below -10 C, and the mixture was stirred at about -10 C for 1 hour. A solution of 1D (10 g, 39 mmol) in dry tetrahydrofuran (100 mL) was added dropwise to the reaction solution, maintaining the temperature at -10 C, and the reaction was carried out at room temperature for 4 hours. The temperature was reduced to about -10 C, and the saturated ammonium chloride solution (40 mL) was added dropwise. The mixture was stirred for 10 minutes. The pH was adjusted to 5 to 6 with 3 mol / L hydrochloric acid solution, (50 mL x 2). The organic phases were combined and washed with saturated sodium chloride solution (30 mL x 2). The organic phase was dried over anhydrous sodium sulfate, filtered, concentrated, and column chromatography (petroleum ether / Ethyl acetate (v / v) = 50: 1-8: 1),To give light yellow solid 1E (10.1 g, yield 83.5%).

The synthetic route of 399-94-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sichuan Haisco Pharmaceutical Co.,Ltd.; FAN, JIANG; ZHANG, CHEN; PENG, FEI; WU, YE; FENG, JIANCHUAN; WANG, JIANMIN; ZHENG, SUXIN; WEI, YONGGANG; YE, FEI; (350 pag.)TW2017/8220; (2017); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 55289-36-6, 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. 55289-36-6, name is 3-Bromo-2-methylaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a mixture of 3-bromo-2-methyl-aniline (10 g, 53.75 mmol) and 4,4,5,5-tetramethyl-2- (4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-l,3,2-dioxaborolane (27.30 g, 107.50 mmol) in dioxane (300 mL) were added KOAc (10.55 g, 107.50 mmol) and Pd(dppf)Cl2(3.93 g, 5.37 mmol) under N2.The mixture was stirred at 90 C for 12 h, and then concentrated. The residue was purified by flash silica gel chromatography (ISCO; 120 g SEP FLASH Silica Flash Column, Eluent of 0-15% Ethyl acetate/Petroleum ether gradient 100 mL/min) to give 2- methyl-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)aniline (8 g, 56.82% yield) as a yellow solid. LCMS: m/z found 234.2 [M+H]+.

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, 3-Bromo-2-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARBUTUS BIOPHARMA, INC.; BI, Yingzhi; DORSEY, Bruce D.; FAN, Yi; MOORE, Christopher Brooks; NGUYEN, Duyan; (169 pag.)WO2019/191624; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 937046-98-5, 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 937046-98-5 as follows.

A mixture of 7-bromopyrrolo[2,l-f][l,2,4]triazin-4-amine (670.0 mg, 3.15 mmol), palladium acetate (70.6 mg, 0.31 mmol), l,3-bis(diphenylphosphino)propane (142.7 mg, 0.35 mmol), potassium carbonate (652.0 mg, 4.72 mmol), and 1-butanol (4 mL) in DMF (4 mL) was stirred under carbon monoxide at 80 0C for 4 h. The solid was filtered away and the filtrate was purified by HPLC using a gradient of 25 – 50% of MeCN in water to yield 107.3 mg (15%) of the title compound as a white solid. 1H-NMR (DMSO-J6) delta 8.28 (bs, 1 H), 8.17, (bs, 1 H), 8.05 (s, 1 H), 7.25 (d, J = 4.7 Hz, 1 H), 7.00 (d, J = 4.6 Hz, 1 H), 4.24 (t, 7 = 6.6 Hz, 2 H), 1.694.62 (m, 2 H), 1.45-1.36 (m, 2 H), 0.92 (t, J = 7.3, 3 H); MS [MH-H]+ = 235.2; LCMS RT = 2.73 min.

According to the analysis of related databases, 937046-98-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2007/64931; (2007); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 15155-41-6,Some common heterocyclic compound, 15155-41-6, name is 4,7-Dibromo-2,1,3-benzothiadiazole, molecular formula is C6H2Br2N2S, 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.

Into a 500 ml three-necked flask equipped with a refluxing condenser, 10.0 g (FW: 293.96; 34 mmole) of 4,7-dibromobenzothiadiazole and 400 ml of ethanol as the solvent were placed. Under cooling with ice, 24.2 g (FW: 37.83; 640 mmole) of sodium borohydride was added, and the resultant mixture was sufficiently stirred for about 2 hours. When generation of a gas (hydrogen sulfide) was not observed any more, the temperature was adjusted at the room temperature, and the reaction mixture was left standing for one night (about 14 hours). Then, the solvent was completely removed under a reduced pressure, and about 400 ml of water was added to dissolve the residue. The resultant solution was left standing for one night, and the object product was recrystallized (7.17 g). The obtained product was treated by extraction with ethyl ether three times, washed with a saturated aqueous solution of sodium chloride, dried with anhydrous sodium sulfate and filtered. After diethyl ether was removed by distillation, 0.88 g of the object compound (3,6-dibromo-1,2-diaminobenzene) was obtained. The overall yield was 82%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4,7-Dibromo-2,1,3-benzothiadiazole, its application will become more common.

Reference:
Patent; IDEMITSU KOSAN CO., LTD.; EP1749823; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 960203-41-2, name is (2-Bromophenyl)(2,4-dimethylphenyl)sulfane, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of (2-Bromophenyl)(2,4-dimethylphenyl)sulfane

Intermediate 1 (Formula IV) obtained in the manner of Example 1 (10.0 g, 34 mmol),N-Boc-piperazine (7.0 g, 38 mmol) was dissolved in 50 ml of toluene.The mixture was stirred under nitrogen for 10 minutes at room temperature (25 C). To the mixture was added tris(dibenzylideneacetone)dipalladium (312 mg, 0.34 mmol),Racemic 2,2-bis(diphenylphosphino)-1,1-biphenyl (637 mg, 1.02 mmol),Sodium tert-butoxide (3.9 g, 41 mmmol),Re-nitrogen replacement.Heat to reflux under nitrogen and react for 12 h.After the reaction was completed, it was cooled to room temperature and filtered through celite.The filtrate was washed with saturated brine and toluene was removed under reduced pressure.Obtained a brown oil(N-Boc-fluoxetine) 14.2 g.

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 960203-41-2.

Reference:
Patent; Shandong Jingwei Pharmaceutical Co., Ltd.; Guo Xiao; Liu Qun; Sang Wei; Qu Aicun; Sun Huifeng; (13 pag.)CN110054600; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 111721-75-6, These common heterocyclic compound, 111721-75-6, name is 2-Bromo-3-fluoroaniline, 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.

General procedure: 4-Amino-7-X-8-bromo-N-(alkyl)-cinnoline-3-carboxamide (X = H or F).To a solution of 2-[(3-X-2-bromophenyl)-hydrazono]-N-(alkyl)-2-cyanoacetamide (1.0 equiv) in anhydrous toluene (0.1 M, 1 volume) was added aluminum chloride (3.0 equiv). The reaction was heated with vigorous stirring at 70-90 C for 1-3 h, cooled, and quenched with Rochelle’s salt (saturated aqueous potassium sodium tartrate, 0.5 volume). Afterward, the mixture was stirred at room temperature overnight. The aqueous layer was separated, and the organic layer was treated with fresh Rochelle’ salt (0.5 volume) while stirring at room temperature for 1 h. After separating the resulting layers, the organic suspension was washed with water and filtered to give give a tan solid. Additionally, the organic filtrate was concentrated, and triturated with ether to give a tan precipitate. The resulting solids were filtered to give a tan solid in 30-70% yield of crude product. The combined tan solid was dried at 50 C under high-vacuum to give the title compound, which was used without further purification.The intermediate compounds were prepared as follows:2-[(3-X-2-Bromophenyl)-hydrazono]-N-(alkyl)-2-cyanoacetamide (X = H or F).Solution A: To a mechanically stirred solution of 3-X-2-bromoaniline (1.0 equiv) in acetic acid (2 M, 1 volume) was added water (0.6 volume) at ambient temperature. The mixture was cooled to 0 C, and then concentrated aqueous HCl (0.5 volume) added. A precipitate was formed immediately and the suspension was stirred at 0 C for 20 min. To this suspension was added dropwise a solution of sodium nitrite (1.10 equiv) in water (0.6 volume), maintaining the internal temperature below 5 C. The resulting clear orange solution was stirred at 0 C for another 30 min.Solution B: To a mechanically stirred solution of N-(alkyl)-2-cyanoacetamide (1.25 equiv) in ethanol (4.5 volume) was added a solution of sodium acetate (1.60 equiv) in water (120 volume), and chilled to between 0 C and -5 C.Solution A was poured into solution B, maintaining the internal temperature below 0 C. An orange precipitate was formed gradually. The mixture was stirred below 0 C overnight, and then the orange precipitate was collected by filtration, washed with water (100 mL × 3), and dried at 50 C under high vacuum to remove water. An orange solid was obtained in greater than 95% yield, which was the ‘E’, and used for the next step without further purification.

Statistics shows that 2-Bromo-3-fluoroaniline is playing an increasingly important role. we look forward to future research findings about 111721-75-6.

Reference:
Article; Alhambra, Cristobal; Becker, Chris; Blake, Timothy; Chang, Amy; Damewood Jr., James R.; Daniels, Thalia; Dembofsky, Bruce T.; Gurley, David A.; Hall, James E.; Herzog, Keith J.; Horchler, Carey L.; Ohnmacht, Cyrus J.; Schmiesing, Richard Jon; Dudley, Adam; Ribadeneira, Maria D.; Knappenberger, Katherine S.; MacIag, Carla; Stein, Mark M.; Chopra, Maninder; Liu, Xiaodong F.; Christian, Edward P.; Arriza, Jeffrey L.; Chapdelaine, Marc J.; Bioorganic and Medicinal Chemistry; vol. 19; 9; (2011); p. 2927 – 2938;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 3344-70-5, 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. 3344-70-5, name is 1,12-Dibromododecane belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a stirred solution of n-dibromoalkane (1 equiv.) in anhydrous THF (0.1M) under an argon atmosphere was added tert-BuOK (1.15 equiv.) in portionwise over 30 min. After being stirred under reflux for 16h, the reaction was cooled and subsequently quenched with water. The resulting mixture was then diluted with diethylether, and the layers were separated. The aqueous layer was extracted several times with diethylether, and the combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The resultant crude product was purified by flash column chromatography over silica gel using petroleum ether as eluent to afford the desired product.

The synthetic route of 1,12-Dibromododecane has been constantly updated, and we look forward to future research findings.

Reference:
Article; Saied, Essa M.; Le, Thuy Linh-Stella; Hornemann; Arenz, Christoph; Bioorganic and Medicinal Chemistry; vol. 26; 14; (2018); p. 4047 – 4057;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 138526-69-9, A common heterocyclic compound, 138526-69-9, name is 1-Bromo-3,4,5-trifluorobenzene, molecular formula is C6H2BrF3, 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.

General procedure: PN (0.004 mol) was dissolved in anhydrous tetrahydrofuran (10 mL). The solution was added dropwise to the appropriate Grignard reagent (0.006 mol, 1 mol/L in tetrahydrofuran, prepared from respective bromide and magnesium) via a syringe at -40 C. After stirring for 20 min, the reaction was moved to ice-bath and quenched with saturated aqueous solution of ammonium chloride. The aqueous phase was extracted with dichloromethane and the combined organic layer was washed with brine, dried over anhydrous sodium sulfate. The solvent was evaporated and the residue was dissolved in dichloromethane and treated with DDQ (0.004 mol). The reaction was refluxed for 3 h, filtered to move the precipitate. The crude product was further purified by column chromatography (petrol ether: ethyl acetate = 5:1) [21].

The synthetic route of 138526-69-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Ya-Nan; Feng, Yi-An; Li, Zhong; Shao, Xu-Sheng; Chinese Chemical Letters; vol. 28; 6; (2017); p. 1228 – 1231;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 17247-58-4, 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 17247-58-4 as follows.

A stirred solution of the ketimime 1a’ (50 g, 187.1 mmol, available from Aldrich Chemical Company, Milwaukee, Wis.) under N2 in dry THF (400 mL) was cooled to -78 C. and treated with 1 M solution of K-tBuO (220 mL, 1.15 equiv.) in THF. The reaction mixture was warmed to 0 C. and stirred for 1 h and treated with bromomethylcyclobutane (28 mL, 249 mmol). The reaction mixture was stirred at room temperature for 48 h and concentrated in vacuo. The residue was dissolved in Et2O (300 mL) and treated with aq. HCl (2 M, 300 mL) The resulting solution was stirred at room temperature for 5 h and extracted with Et2O (1 L). The aqueous layer was made basic to pH 12-14 with aq. NaOH (50%) and extracted with CH2Cl2 (3×300 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated to give pure amine (1b’, 18 g) as a colorless oil.

According to the analysis of related databases, 17247-58-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Schering Corporation; US2006/275366; (2006); A1;,
Bromide – Wikipedia,
bromide – Wiktionary