Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
CAS No. : | 288105-04-4 | MDL No. : | MFCD12911571 |
Formula : | C20H17BO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 300.16 | Pubchem ID : | - |
Synonyms : |
|
Signal Word: | Warning | Class: | |
Precautionary Statements: | P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330 | UN#: | |
Hazard Statements: | H302-H315-H319 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | With sodium hydrogencarbonate In tetrahydrofuran at 75℃; for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | With sodium hydrogencarbonate In tetrahydrofuran at 75℃; for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene; for 10h;Heating / reflux; | Under an atmosphere of argon, 9-bromo-10-(2-naphthyl)anthracene (3.2 g, 8.4 mmole), 4-(2,2diphenylvinyl)phenylboric acid (2.8 g, 9.3 mmole, 1.1 eq) and tetrakis(triphenylphosphine)palladium(0) (0.19 g, 0.16 mmole, 2% Pd) were suspended in toluene (30 ml). To the obtained suspension, a 2M aqueous solution of sodium carbonate (3 g, 28 mmole, 3 eq/15 ml) was added, and the resultant mixture was refluxed for 10 hours. The obtained reaction mixture was filtered and washed with toluene, water and methanol, and a light yellow solid substance (3.7 g) was obtained. The solid substance was suspended in boiling toluene (40 ml), cooled while being left standing and filtered, and a light yellow solid substance (3.4 g, the yield: 73%) was obtained. The result of examination of the obtained product in accordance with 1H-NMR was as follows: 1H-NMR (CDCl3, TMS) delta: 7.15 (1H, s), 7.2-7.4 (17H, m), 7.5-7.8 (8H, m), 7.8-8.1 (4H, m). The obtained solid substance (3.4 g) was purified by sublimation at 340C/10-6 Torr for 1 hour, and a light yellow substance (2.9 g) was obtained. It was confirmed in accordance with the field desorption mass analysis (FDMS) that the obtained product was the object compound (Compound (A1)). The results of measurements of the energy gap Eg, the ionization potential Ip and the glass transition temperature Tg are also shown in the following. FDMS: calcd. for C44H30=558, found m/z=558 (M+, 100)lambdamax: 397, 378, 359 nm (PhMe)Fmax: 438 nm (PhMe: lambdaex=397 nm)Ip=5.71 eV (100 nW, 27 Y/eV)Tg=108C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With sodium carbonate In water; toluene for 10h; Heating / reflux; | 2.4 Under an atmosphere of argon, 9-bromo-10-(3,5-diphenylphenyl)-anthracene (3.9 g, 8.0 mmole), 4-(2,2-diphenylvinyl)phenylboric acid (2.7 g, 9.0 mmole, 1.1 eq) and tetrakis(triphenylphosphine)palladium(0) (0.18 g, 0.16 mmole, 2% Pd) were suspended in toluene (30 ml). To the obtained suspension, a 2M aqueous solution of sodium carbonate (2.9 g, 27 mmole, 3 eq/15 ml) was added, and the resultant mixture was refluxed for 10 hours. An organic layer was separated from the reaction mixture, washed with a saturated aqueous solution of sodium chloride (30 ml) and dried with magnesium sulfate. After the solvent was removed by distillation, a brown solid substance was obtained. The obtained solid substance was purified in accordance with the column chromatography (silica gel/hexane + 10% dichloromethane, hexane + 20% dichloromethane), and a white solid substance (4.3 g, the yield: 81%) was obtained. The result of examination of the obtained product in accordance with 1H-NMR was as follows: 1H-NMR (CDCl3, TMS) δ: 7.15 (1H, s), 7.2-7.5 (24H, m), 7.7-7.9 (10H, m), 8.02 (1H, t, J=2 Hz). The obtained solid substance (4.3 g) was purified by sublimation at 360°C/10-6 Torr for 1 hour, and a light yellow substance (3.2 g) was obtained. It was confirmed in accordance with FDMS that the obtained product was the object compound (Compound (A2)). The results of measurements of Eg, Ip and Tg are also shown in the following. FDMS: calcd. for C52H30=660, found m/z=660 (M+, 100)λmax: 397, 377, 359 nm (PhMe)Fmax: 435 nm (PhMe: λex=397 nm)Ip=5.82 eV (100 nW, 27 Y/eV)Tg=120°C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triphenylphosphine; palladium dichloride In ethanol; water; toluene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
[Exemplary embodiment 8] Synthesis of compound 142 [Compound 142][Synthesis scheme] <n="72"/>(OH)2 K2CO3 P d(PPhOl4 THF Together with triethylphosphite (25g, ldeltaOmmol), 1- bromo-4-bromomethylbenzene (5g, 20mmol) was put into an agitator to have them react to each other for two hours at 120C to thereby synthesize triethyl A- bromobenzylphosphite. The synthesized triethyl 4- bromobenzylphosphite (6.1Aq, 2OmInOl), benzophenone (5.13g, 29.1betammol) and potassium tert-butoxide (3.27g, 29.1betammol) were put into a reactor and melted by THF of 50ml to have them react to each other for four hours at 120C to thereby synthesize l-bromo-4- (2, 2- diphenylvinyl) benzene (1-1) . The synthesized-bromo-4- (2, 2- diphenylvinyl) benzene (1-1) (beta.03g, ldeltammol) was melted by THF of 50ml, gradually added with 2Mn-BuLi (10ml, 20mmol) at -78 C and agitated for one hour at low temperatures. The mixture was gradually added with triisopropyl borate <n="73"/>(3.76g, 20mmol) at -78C, agitated for one hour at low temperatures and then additionally agitated for 30 minutes at 0C to thereby synthesize 4- (2, 2- diphenylvinyl) phenylboronic acid (1-2) . The synthesized 4- (2, 2-diphenylvinyl) phenylboronic acid (4.5g, 15mmol) (l-2), K2CO3 (6.2g, 45mmol) and Pd (PPh3) 4 (0.8betag, 0.75mmol) were melted by THF (60ml), added with (E) -3- (5- bromothieno [3, 2-b] thiophene-2-yl) -2-cyanoacrylic acid(5.6g, 18mmol) , agitated for four hours at 120C to complete the reaction. After extracting an organic layer from the mixture with dichloromethane and distilled water, the solvent was removed through an evaporator and the organic layer was recrystallized by n-hexane and dried to collect the compound 142 after the sediment was filtered. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With n-butyllithium; In tetrahydrofuran; at -78 - 20℃;Inert atmosphere; | To a schlenk-type tube containing the solution of <strong>[18648-66-3]1-bromo-4-(2,2-diphenylvinyl)benzene</strong> (5.36 g, 16.0 mmol) in 60 mL dried THF under N2 atmosphere at -78 C was added dropwise 1.6 M n-BuLi (12.7 mL, 20.4 mmol). The reaction mixture was stirred for 2 h at -78 C, and then trimethylborate (2.72 mL, 24.0 mmol) was added. The mixture was allowed to warm to room temperature and stirred overnight. The reaction was quenched by water, followed by acidifying with 25 mL HCl (6 M). The solution was extracted with ethylether. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and evaporated. The crude product was purified on a silica gel column using petroleum/ethyl acetate (v/v = 2:1) as eluent affording a white solid (2.40 g, yield 50.0%).1HNMR (CDCl3, 300 MHz, ppm) delta: 6.96-7.02 (m, 3H), 7.14 (br, 2H), 7.29-7.49 (m, 10H).13CNMR (CDCl3, 75.5 MHz, ppm) delta: 126.90, 127.20, 127.24, 127.42, 127.72, 127.88, 128.35, 128.38, 129.24, 130.04, 133.10, 139.15, 140.48, 143.22. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92.6% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In tetrahydrofuran at 70℃; Inert atmosphere; | 1,3,6,8-Tetrakis[4-(2,2-diphenylvinyl)phenyl]pyrene (TPVPP) General procedure: A two-necked flask was charged with 1-bromopyrene (0.13 g, 0.45 mmol), 4-(2,2-diphenylvinyl)phenylboronic acid (0.30 g, 1.00 mmol), Pd(PPh3)4, and well-degassed THF (30 mL) under N2 atmosphere. After the mixture was stirred for 10 min, sodium carbonate (4 mL, 2 M) was added to the flask. The mixture was then allowed to increase to 70 oC and maintained for 24 h. The solution was extracted with dichloromethane. The organic layer was washed with brine, and dried over Na2SO4. The solvent was evaporated under reduced pressure, and the crude product was purified by flash column chromatography using petroleum/dichloromethane (v/v = 16:1) as eluent to afford a white solid (0.15 g, yield 73.2%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With tetrakis(triphenylphosphine) palladium(0); tricaprylylmethyl ammoniumchloride; potassium carbonate; at 90℃; for 16h;Inert atmosphere; | General procedure: A mixture of 1-(4-bromophenyl)-1,2,2-triphenylethylene (1) (200 mg, 0.48 mmol) and 4-(2,2-diphenylvinyl)phenylboronic acid (8) (174 mg, 0.58 mmol) were dissolved in toluene (10 mL) under argon atmosphere. Aqueous solution of K2CO3 (2 ml, 2 M), tricaprylylmethyl ammoniumchloride (Aliquat 336) (3 drops) and Pd(PPh)4 (10 mg) was added to the mixture. The reaction mixture was heated at 90 ºC overnight. After being cooled to room temperature, distilled water (5 mL) was added and extracted with dichloromethane (3×10 mL). Organic layer was dried over anhydrous Na2SO4. The solvent was removed under reduced pressure, the residue was purified using column chromatography (silica gel/ethyl acetate: petroleum ether 5:95) affoarded the compound 10 (240 mg, 85%) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 24h; Inert atmosphere; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73.2% | Under a nitrogen atmosphere, <strong>[100125-12-0]3,8-dibromophenanthroline</strong> (0.135 g, 0.40 mmol), [4-(2,2-diphenylvinyl)phenyl]boronic acid (0.30 g, 1.00mmol), tetrakis(triphenylphosphine)palladium, 20mL of tetrahydrofuran, 15ml of ethanol, stirred at room temperature for 10min. To the reaction system, 4 mL of aqueous sodium carbonate solution (2M) was added, followed by reaction at 110 C for 24 h. After the reaction was completed, most of the tetrahydrofuran was distilled off, extracted with methylene chloride, washed with water, dried over anhydrous sodium sulfate, concentrated and purified by column chromatography (SiO2, eluent dichloromethane / ethyl acetate 1: 1 by volume) gave 0.15 g of yellow solid BDP in 73.2% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | Under nitrogen atmosphere, <strong>[66127-01-3]3-bromophenanthroline</strong> (0.10 g, 0.40 mmol), 4-(2,2-diphenylvinyl)phenyl]boronic acid (0.14 g, 0.48mmol), tetrakis(triphenylphosphine)palladium, 20mL of tetrahydrofuran was added 100mL three-necked round bottom flask was stirred at room temperature for 10min, the reaction system was added 4mL aqueous solution of sodium carbonate (2M) and reacted at 70 C for 24 h. After the reaction was completed, most of the tetrahydrofuran was distilled off, extracted with methylene chloride, washed with water, dried over anhydrous sodium sulfate, concentrated and subjected to column chromatography (SiO2, eluent: dichloromethane / methanol = 19: 1) afforded 0.12 g of the DP product in 69.0% yield. |