Category: 927384-44-9

Application of 927384-44-9, 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 927384-44-9 as follows.

Bromo-1-(2,3-dihydro-1H-naphtho[1,8-de]-1,3,2-diazaborinyl)-benzene 11 (2.40 g, 7.43 mmol), 4-(ethoxycarbonyl)phenylboronicacid 12 (2.40 g, 12.4 mmol), powdered tripotassium phosphate(3.40 g, 20.7 mmol) and 1,4-dioxane (150 cm3) were added to around-bottom flask fitted with a condenser and heated at 80 Cfor 15 min under N2. Pd(PPh3)4 (0.47 g, 0.41 mmol) was added tothe mixture which was purged with N2 for a further 15 min beforebeing stirred at 80 C for 2 days. The mixture was allowed to cool,filtered and the filtrate concentrated under reduced pressure. Theresulting residue was dissolved in chloroform (100 cm3), washedwith water (3 x 50 cm3) and brine (50 cm3) and concentratedunder reduced pressure to give a brown solid, which wasrecrystallised from chloroform and methanol to give 13 as largeyellow needles (yield 2.07 g, 71%). 1H NMR (CDCl3, 400 MHz) delta 8.25-8.04 (m, 2H), 7.85-7.67 (m, 6 H), 7.19 (dd, J = 7.3, 8.2 Hz,2H), 7.11 (d, J = 7.8 Hz, 2H), 6.48 (dd, J = 0.8, 7.3 Hz, 2H), 6.11 (s,2 H), 4.45 (q, J = 7.2 Hz, 2H), 1.46 (t, J = 7.2 Hz, 3H). ESI-TOF-MS:m/z 392.23 [M]+. Elemental Anal. Calc. for C25H21BN2O2: C, 76.55;H, 5.40; N, 7.14. Found: C, 76.51; H, 5.33; N, 7.26%. ATR-FTIR(cm-1): 3360 (s), 2900 (m), 1590 (s), 1580 (s), 1360 (m), 1260(s), 1080 (m), 756 (m, br), 728 (m).

According to the analysis of related databases, 927384-44-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Argent, Stephen P.; Tarassova, Irina; Greenaway, Alex; Nowell, Harriot; Barnett, Sarah A.; Warren, Mark R.; Tang, Chiu C.; Morris, Christopher G.; Lewis, William; Champness, Neil R.; Schroeder, Martin; Blake, Alexander J.; Polyhedron; vol. 120; (2016); p. 18 – 29;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 927384-44-9, 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 927384-44-9 as follows.

Bromo-1-(2,3-dihydro-1H-naphtho[1,8-de]-1,3,2-diazaborinyl)-benzene 11 (2.40 g, 7.43 mmol), 4-(ethoxycarbonyl)phenylboronicacid 12 (2.40 g, 12.4 mmol), powdered tripotassium phosphate(3.40 g, 20.7 mmol) and 1,4-dioxane (150 cm3) were added to around-bottom flask fitted with a condenser and heated at 80 Cfor 15 min under N2. Pd(PPh3)4 (0.47 g, 0.41 mmol) was added tothe mixture which was purged with N2 for a further 15 min beforebeing stirred at 80 C for 2 days. The mixture was allowed to cool,filtered and the filtrate concentrated under reduced pressure. Theresulting residue was dissolved in chloroform (100 cm3), washedwith water (3 x 50 cm3) and brine (50 cm3) and concentratedunder reduced pressure to give a brown solid, which wasrecrystallised from chloroform and methanol to give 13 as largeyellow needles (yield 2.07 g, 71%). 1H NMR (CDCl3, 400 MHz) delta 8.25-8.04 (m, 2H), 7.85-7.67 (m, 6 H), 7.19 (dd, J = 7.3, 8.2 Hz,2H), 7.11 (d, J = 7.8 Hz, 2H), 6.48 (dd, J = 0.8, 7.3 Hz, 2H), 6.11 (s,2 H), 4.45 (q, J = 7.2 Hz, 2H), 1.46 (t, J = 7.2 Hz, 3H). ESI-TOF-MS:m/z 392.23 [M]+. Elemental Anal. Calc. for C25H21BN2O2: C, 76.55;H, 5.40; N, 7.14. Found: C, 76.51; H, 5.33; N, 7.26%. ATR-FTIR(cm-1): 3360 (s), 2900 (m), 1590 (s), 1580 (s), 1360 (m), 1260(s), 1080 (m), 756 (m, br), 728 (m).

According to the analysis of related databases, 927384-44-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Argent, Stephen P.; Tarassova, Irina; Greenaway, Alex; Nowell, Harriot; Barnett, Sarah A.; Warren, Mark R.; Tang, Chiu C.; Morris, Christopher G.; Lewis, William; Champness, Neil R.; Schroeder, Martin; Blake, Alexander J.; Polyhedron; vol. 120; (2016); p. 18 – 29;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 927384-44-9, name is 2-(4-Bromophenyl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine, molecular formula is C16H12BBrN2, 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: C16H12BBrN2

A suspension of 1,8-diaminonaphthalene protected p-bromobenzeneboronic acid (1.61 g, 5.0mmol), B2pin2 (1.90 g 7.5 mmol), KOAc (1.47 g, 15.0 mmol) and PdCl2(dppf) (204 mg, 0.25mmol) in DMF (100 mL) was stirred at 80 C for 3 h. The mixture was extracted with EtOAc and washed with brine. The organic layer was separated and dried over Na2SO4. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (EtOAc), preparative SEC using CHCl3 as the eluent, and recrystallization (CH2Cl2-Hexane) to give 18 as a white solid (1.34 g, 72%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 927384-44-9, its application will become more common.

Reference:
Article; Terao, Jun; Konoshima, Yohei; Matono, Akitoshi; Masai, Hiroshi; Fujihara, Tetsuaki; Tsuji, Yasushi; Beilstein Journal of Organic Chemistry; vol. 10; (2014); p. 2800 – 2808;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 927384-44-9, 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. 927384-44-9, name is 2-(4-Bromophenyl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine, This compound has unique chemical properties. The synthetic route is as follows.

A four-necked flask,4-hydroxy-phenyl boric acid 20.0g (0.15 mol),1,8-diaminonaphthalene protection p- bromophenyl boric acid 46.8g (0.15 mol),Take a potassium carbonate 31.1g (0.23 mol),Ethanol 140mL, was suspended in water 47mL.After the inside the flask was replaced by nitrogen gas,The addition of tetrakistriphenylphosphine palladium (0) 1.7g (1.5 mmol). After the mixture was heated with stirring for 7 hours at 80 ,It was diluted with toluene 300mL,It was separated treated with 5% hydrochloric acid 300mL.The solvent was evaporated,The compound represented by formula (I-60-1) by recrystallizing with acetone / hexane mixed solventIt was obtained 42.9g (0.13 mol).

The chemical industry reduces the impact on the environment during synthesis 2-(4-Bromophenyl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; DIC Corporation; Horiguchi, Masahiro; Hayashi, Masanao; Kusumoto, Tetsuo; (63 pag.)JP5962949; (2016); B2;,
Bromide – Wikipedia,
bromide – Wiktionary