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CAS No. : | 5122-95-2 | MDL No. : | MFCD01318102 |
Formula : | C12H11BO2 | Boiling Point : | - |
Linear Structure Formula : | (C6H5)C6H4B(OH)2 | InChI Key : | GOXICVKOZJFRMB-UHFFFAOYSA-N |
M.W : | 198.03 | Pubchem ID : | 2734315 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
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 |
---|---|---|
77% | With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In toluene; for 18h;Inert atmosphere; Heating; | Example 4 This example illustrates the preparation of a compound having Formula I, 4',4"-(diphenylmethylene)N,N-bis(3-(biphenylen-1 -yl-4- methyl)phenyl)aniline), Compound 3 below. Compound 3 a. 5-chloro-3'-phenyl-2-methylbiphenyl To a 2 L round bottle flask equipped with reflux condenser, stir bar, nitrogen feed, and oil bath were added <strong>[27139-97-5]2-bromo-4-chlorotoluene</strong> (20.67 g, 98.59 mmol), 3-biphenylboronic acid (20.50 g 103.52 mmol), sodium carbonate (158 mL, 31 5 mmol), Aliquat 336 (4.00 g) and toluene (600 mL). Solution was purged with nitrogen for 20 minutes before addingtetrakis(triphenylphospine)palladium(0) (1 .14 g, 0.98 mmol) and purged for another 10 minute. The reaction was then heated under nitrogen for 18 hour. After cooing to ambient temperature, the organic phase was separated, washed with 1 0percent HCI (200mL), water (200mL) and saturated brine (200mL). This solution was dried with magnesium sulfate (50 g) for 3 hour and the solvent was removed by rotary evaporation. The crude product was filtered, washing with with hexane. Product containing fractions were identified by UPLC and collected. Low boiling point impurities and solvents were removed by Kruger-Rohr distillation to give the product as colorless oil (20.2 g, 77percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; water; for 16h;Inert atmosphere; Reflux; | 2) Synthesis of compound (140-b) [0246] [0247] In a three-neck flask, 10.0g (50.5 mmol) of compound (140-a), 14.8g (45.5 mmol) of compound (140-b), 75 mL of a 2M aqueous sodium carbonate solution, 150 mL of 1,2-dimethoxyethane and 2.92 g (2.53 mmol) of Pd(PPh3)4 were placed. The resulting mixture was refluxed for 16 hours in a nitrogen atmosphere. [0248] After completion of the reaction, the sample solution was transferred to a separating funnel, and extracted with ethyl acetate several times. The resultant was dried with anhydrous magnesium sulfate, filtrated and concentrated. The resulting product was purified by silica gel chromatography (hexane), whereby white solids were obtained. The yield was 12.0g (60percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 55℃; for 12.0h;Inert atmosphere; | 500 mL roundbottom flask 10.0 g intermediate A (39.2 mmol), the intermediate a-82-1(dealer:. Beijing pure chem ) 7.8 g(39.2 mmol), potassium carbonate 13.5 g (98.0 mmol), tetrakis(triphenylphosphine) palladium 1,4 (0), 2.3 g (2.0 mmol)Dioxane gave after it in 140 mL, 70 mL water, and heated 55 degrees for 12hours under a nitrogen flow. Obtained from this oneThe mixture was filtered, and then the crystallized solid was added to methanol500 mL, dissolved in monochlorobenzene silica gel / CeliteFiltered, to give after removing an appropriate amount of an organic solvent,and recrystallized in methanol and a-82-2 (10.1 g, yield of 69%). |
69% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 60℃; for 12.0h;Inert atmosphere; | Intermediate B (10.0 g, 39.2 mmol), 3-biphenyl boronic acid (12.1 g, 43.1 mmol), potassium carbonate (13.5 g, 98.0 mmol) and tetrakis(triphenylphosphine) palladium (0) (2.3 g, 43.1 mmol) were added to 140 mE of 1,4-dioxane and 70 mE of water in a 500 mE flask, and the mixture was heated under a nitrogen flow for 12 hours at 60 C. The obtained mixture was added to 500 mE of methanol, andsolid crystallized therein was filtered, dissolved in monochlorobenzene, filtered through silica gel/Celite, and then, afier removing appropriate amount of an organic solvent, recrystallized with methanol to obtain Intermediate B-3-2 (10.1 g, yield of 69%). calcd. C22H13C1N25: C, 70.87; H, 3.51; Cl, 9.51; N, 7.51; S,8.60; found: C, 70.80; H, 3.50; Cl, 9.47; N, 7.49; 5, 8.60. |