Category: 4549-33-1

Some common heterocyclic compound, 4549-33-1, name is 1,9-Dibromononane, molecular formula is C9H18Br2, 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. 4549-33-1

n-BuLi (1.63 M in hexane, 4.0 mL, 6.52 mmol) was added to a solution of iPr2NH (0.62 mL, 4.4 mmol) in tetrahydrofuran (THF) (5 mL) at 0C, and the whole mixture was stirred for 30 min at 0C. 3-Picoline (0.39 mL, 4.02 mmol) was added to the mixture at -78C, and the whole mixture was stirred for 20 min. Then, 1,9-dibromononane (2.43 mL, 12 mmol) was added to the mixture, and the whole mixture was gradually warmed to r.t. with stirring overnight. Sat. NaHCO3aq. was added to the reaction mixture, and the whole mixture was extracted with AcOEt. The combined organic layer was washed with brine and dried (Na2SO4). Removal of the solvent under reduced pressure to give a crude product, which was purified by SiO2 column chromatography (hexane-AcOEt=8 : 1) to give 5b(388 mg, 33%).1H-NMR (500 MHz, CDCl3) delta: 8.35-8.30 (2H, m), 7.39 (1H, d, J=7.7 Hz), 7.10 (1H, dd, J=7.7, 4.9 Hz), 3.30 (2H, t, J=6.9 Hz), 2.50 (2H, t, J=7.7 Hz), 1.74 (1H, quint, J=7.1 Hz), 1.53-1.48 (2H, m), 1.35-1.12 (12H, m). 13C-NMR (125 MHz, CDCl3) delta: 149.6, 146.8, 137.6, 135.5, 123.0, 33.8, 32.7, 32.5, 30.8, 29.11, 29.10, 29.07, 28.8, 28.4, 27.9. IR (KBr) cm-1: 2926, 2854, 1574, 1422, 1026. ESI-TOF-MS m/z: 298 (M+H)+. HRESI-TOF-MS m/z: 298.1163 (Calcd for C15H25NBr: 298.1170).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4549-33-1, its application will become more common.

Reference:
Article; Arai, Masayoshi; Kamiya, Kentaro; Shin, Dayoung; Matsumoto, Hirokazu; Hisa, Tomoya; Setiawan, Andi; Kotoku, Naoyuki; Kobayashi, Motomasa; Chemical and Pharmaceutical Bulletin; vol. 64; 7; (2016); p. 766 – 771;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 4549-33-1, name is 1,9-Dibromononane, A new synthetic method of this compound is introduced below., 4549-33-1

General procedure: Finely ground KOH(4.48 g, 80 mmol) was added to a solution of pyrazole(2.72 g, 40 mmol) in DMSO (20 ml). The suspension wasthoroughly stirred for 30 min at 80, then treated bydropwise addition of 1,4-dibromobutane (4.32 g, 2.41 ml,20 mmol) in DMSO (10 ml) over 30 min, while cooling thereaction mixture with water. After finishing the addition ofdibrom derivative, stirring and heating at 80 wascontinued for additional 4 h, the reaction mixture wasthen poured into water (200 ml), extracted withchloroform (5¡Á10 ml), the extract was washed one timewith distilled water (10 ml) and dried over anhydrousCaCl2. Chloroform was removed by distillation undervacuum.

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; Zatonskaya, Lina V.; Schepetkin, Igor A.; Petrenko, Tatiana V.; Ogorodnikov, Vladimir D.; Khlebnikov, Andrei I.; Potapov, Andrei S.; Chemistry of Heterocyclic Compounds; vol. 52; 6; (2016); p. 388 – 401; Khim. Geterotsikl. Soedin.; vol. 52; 6; (2016); p. 388 – 401,14;,
Bromide – Wikipedia,
bromide – Wiktionary

4549-33-1, 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 4549-33-1 as follows.

4-Picoline (2.0 mL, 21 mmol) was dissolved in THF (40 mL) under an argon atmosphere using a 150 mL Schlenk flask. The Schlenk flask was cooled down to-78C by using a dry ice/methanol cooling bath. A solution of n-butyllithium in hexane (12.0 mL, 18 mmol) was added to the solution by a syringe under an argon atmosphere. After the solution was stirred for 30 min, diethyl amine (2.2 mL, 22 mmol) was added to the solution by a syringe under an argon atmosphere. After the solution was stirred for 30 min, the solution was added to a solution of 1,9-dibromononane (20.0 mL, 99 mmol) in THF (10 mL) by a syringe under an argon atmosphere. The reaction mixture was gradually warmed to room temperature and stirred for 1 h. The solution was poured into 0.5M ammonium chloride (10 0mL) to quench the reaction at 0C. After evaporation of the organic solvent at 0C, the residual solution was dropped into 1M hydrobromic acid (100 mL), and the product was extracted with dichloromethane (4¡Á50 mL). The organic layers were combined, and dried with sodium sulfate (15 g). The organic layer was concentrated under reduced pressure. After the residual solution was dropped into hexane (200 mL), and then a pale yellow precipitate was formed. The pale yellow precipitate containing the product was recovered by centrifugation. The product 1 was obtained as a pale yellow powder (yield 5.12g, 65%). 1H NMR (500MHz, DMSO-d6): delta 8.42 (d, J=5.9Hz, 2H), 7.19 (d, J=5.9Hz, 2H), 3.50 (t, J=6.7Hz, 2H), 2.57 (t, J=7.6Hz, 2H), 1.81-1.72 (m, 2H), 1.61-1.52 (m, 2H), 1.39-1.20 (m, 12H).

According to the analysis of related databases, 1,9-Dibromononane, the application of this compound in the production field has become more and more popular.

Reference:
Article; Hashidzume, Akihito; Kuse, Akihiro; Oshikiri, Tomoya; Adachi, Seiji; Yamaguchi, Hiroyasu; Harada, Akira; Tetrahedron; vol. 73; 33; (2017); p. 4988 – 4993;,
Bromide – Wikipedia,
bromide – Wiktionary

The chemical industry reduces the impact on the environment during synthesis 4549-33-1, name is 1,9-Dibromononane, I believe this compound will play a more active role in future production and life. 4549-33-1

General procedure: To a stirred solution of monovalent beta-carbolines 1-17 (2.0 mmol) in anhydrous DMF (30 ml) was added 60% NaH (0.4 g, 10 mmol). After stirring for 20 min at room temperature, the appropriate dibromoalkane (1.0 mmol) was added. And then the reaction mixture was stirred at room temperature for 8-20 h. After completion of the reaction as indicated by TLC, the solution was poured into ice-water and extracted with CH2Cl2. The combined organic layer was washed with water and brine, dried over anhydrous Na2SO4, filtered and evaporated in vacuum. The residue was purified by column chromatography with CH2Cl2/MeOH (50:1) to successfully afford the desirable target products.

The chemical industry reduces the impact on the environment during synthesis 4549-33-1. I believe this compound will play a more active role in future production and life.

Reference:
Article; Shi, Buxi; Cao, Rihui; Fan, Wenxi; Guo, Liang; Ma, Qin; Chen, Xuemei; Zhang, Guoxian; Qiu, Liqin; Song, Huacan; European Journal of Medicinal Chemistry; vol. 60; (2013); p. 10 – 22;,
Bromide – Wikipedia,
bromide – Wiktionary

4549-33-1, 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 4549-33-1 as follows.

General procedure: To a stirred solution of monovalent beta-carbolines 1-17 (2.0 mmol) in anhydrous DMF (30 ml) was added 60% NaH (0.4 g, 10 mmol). After stirring for 20 min at room temperature, the appropriate dibromoalkane (1.0 mmol) was added. And then the reaction mixture was stirred at room temperature for 8-20 h. After completion of the reaction as indicated by TLC, the solution was poured into ice-water and extracted with CH2Cl2. The combined organic layer was washed with water and brine, dried over anhydrous Na2SO4, filtered and evaporated in vacuum. The residue was purified by column chromatography with CH2Cl2/MeOH (50:1) to successfully afford the desirable target products.

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:
Article; Shi, Buxi; Cao, Rihui; Fan, Wenxi; Guo, Liang; Ma, Qin; Chen, Xuemei; Zhang, Guoxian; Qiu, Liqin; Song, Huacan; European Journal of Medicinal Chemistry; vol. 60; (2013); p. 10 – 22;,
Bromide – Wikipedia,
bromide – Wiktionary