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CAS No. : | 1160294-85-8 | MDL No. : | MFCD20257783 |
Formula : | C24H16BrN | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | JBEQRROTSDUCGC-UHFFFAOYSA-N |
M.W : | 398.29 | Pubchem ID : | 57746295 |
Synonyms : |
|
Num. heavy atoms : | 26 |
Num. arom. heavy atoms : | 25 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 113.92 |
TPSA : | 4.93 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -3.54 cm/s |
Log Po/w (iLOGP) : | 3.95 |
Log Po/w (XLOGP3) : | 7.31 |
Log Po/w (WLOGP) : | 7.21 |
Log Po/w (MLOGP) : | 6.09 |
Log Po/w (SILICOS-IT) : | 6.26 |
Consensus Log Po/w : | 6.16 |
Lipinski : | 1.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 1.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -7.49 |
Solubility : | 0.0000128 mg/ml ; 0.000000032 mol/l |
Class : | Poorly soluble |
Log S (Ali) : | -7.24 |
Solubility : | 0.0000229 mg/ml ; 0.0000000575 mol/l |
Class : | Poorly soluble |
Log S (SILICOS-IT) : | -9.94 |
Solubility : | 0.0000000455 mg/ml ; 0.0000000001 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 2.29 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
90% | With N-Bromosuccinimide In ethyl acetate; toluene for 48 h; | Step 1: Synthesis of 3-bromo-6,9-diphenyl-9H-carbazole][0730]A synthetic scheme of 3-bromo-6,9-diphenyl-9H-carbazole in Step 1 is shown in the following (S-I). [0731] <n="245"/>[0732]In a 300-mL erlenmayer flask, 4.8 g (15 mmol) of 3,9-diphenyl-9H-carbazole was put, and 250 mL of a mixture solvent (ethyl acetate: toluene = 4:1) was added to this solution. After that, this mixture was stirred for 30 minutes. Then, 2.7 g (15 mmol) of N-bromo succinimide (abbreviation: NBS) was added to this solution little by little, and the solution was stirred for 48 hours.[0733]After the stirring, this mixture was washed with a saturated sodium hydrogen carbonate solution and a saturated saline solution in this order. After the washing, moisture of the obtained organic layer was removed by magnesium sulfate. Then, suction filtration was performed on this mixture and the magnesium sulfate was removed to obtain filtrate. A small amount of ethanol was added to an oily substance which was obtained by concentrating the obtained filtrate. Then, the mixture was irradiated with supersonic to precipitate a solid. The precipitated solid was collected by suction filtration to obtain 5.4 g of a white powder-like solid at a yield of 90 percent. |
82% | With N-Bromosuccinimide In dichloromethane at 20℃; for 8 h; | The intermediate b (35 g, 82percent) was synthesized by dissolving 34.4 g (107.6 mmol) of compound 1 in 500 ml of dichloromethane, adding 19.2 g (107.6 mmol) of N-bromide (N-bromosuccinimide), and the mixture was stirred at room temperature for 8 hours. |
60% | With N-Bromosuccinimide In N,N-dimethyl-formamide for 3 h; | After dissolving compound C-11-1 (6.4 g, 20.06 mmol) in DMF 100 mL, NBS (3.6 g, 20.06 mmol) was added thereto. The reaction mixture was stirred for 3 hours. After completing the reaction, the mixture was extracted with MC/purified water. After purifying the resultant by a silica column chromatography, compound C-11-2 (4.8 g, 60percent) was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1 h; Stage #2: for 12 h; Stage #3: With hydrogenchloride In tetrahydrofuran; hexane; water |
After dissolving compound C-11-2 (4.8 g, 12.06 mmol) in THF (60 mL), 2.5 M n-BuLi in hexane (6.3 mL, 15.68 mmol) was added thereto at -78°C. The reaction mixture was stirred for 1 hour. B(Oi-Pr)3 (4.5 g, 24.12 mmol) was added slowly to the mixture, and then the mixture was stirred for 12 hours. After completing the reaction, purified water 20 mL was slowly dropped stepwise to the mixture. Thereafter, the mixture was extracted with MC/NH4Cl aq. The obtained organic layer was concentrated, was filtered through silica, and then was crystallized with MC/hexane to obtain compound C-11-3 (3 g, 70percent). |