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CAS No. : | 1055-23-8 | MDL No. : | MFCD00130216 |
Formula : | C28H18 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SXGIRTCIFPJUEQ-UHFFFAOYSA-N |
M.W : | 354.44 | Pubchem ID : | 66105 |
Synonyms : |
|
Num. heavy atoms : | 28 |
Num. arom. heavy atoms : | 28 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 121.9 |
TPSA : | 0.0 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) : | -2.39 cm/s |
Log Po/w (iLOGP) : | 3.95 |
Log Po/w (XLOGP3) : | 8.55 |
Log Po/w (WLOGP) : | 7.97 |
Log Po/w (MLOGP) : | 7.72 |
Log Po/w (SILICOS-IT) : | 7.61 |
Consensus Log Po/w : | 7.16 |
Lipinski : | 1.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 1.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -8.1 |
Solubility : | 0.00000283 mg/ml ; 0.000000008 mol/l |
Class : | Poorly soluble |
Log S (Ali) : | -8.42 |
Solubility : | 0.00000134 mg/ml ; 0.0000000038 mol/l |
Class : | Poorly soluble |
Log S (SILICOS-IT) : | -11.57 |
Solubility : | 0.0000000009 mg/ml ; 0.0 mol/l |
Class : | Insoluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 1.87 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | Packing Group: | N/A |
GHS Pictogram: |
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* 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 |
---|---|---|
93% | First, 9-anthrone (5 g, 26 mmol), zinc powder (8.5 g, 129 mmol), zinc chloride (7 g, 56 mmol) were added to a three-necked flask, and a certain percentage of 100 ml of a mixed solvent of tetrahydrofuran and water was added. The magnet was stirred for more than 8 hours at room temperature, extracted with dichloromethane, dried over anhydrous magnesium sulfate, filtered, spin-dried and dried to give 4.8 g of a yellow solid. The yellow solid was added to the three-necked flask and a small amount of p-toluenesulfonic acid was added. (PTS) using toluene as solvent, refluxing until the solvent becomes clear, extracting with solvent dichloromethane, drying with anhydrous magnesium sulfate as a drying agent, filtering, spin-drying, and purifying by silica gel column to obtain white crystalline solid 4.3 g, yield 93%. | |
With hydrogenchloride; tin; In acetic acid; | Example 1 Preparation of 1:1 [9,9']Bianthracenyl/Toluene adduct Anthrone (40.00 g, 206 mmol) was refluxed in a mixture of glacial acetic acid (200 ml) and concentrated hydrochloric acid (80 ml). To this refluxing solution granulated tin (80 g, 674 mmol) was cautiously added. The reaction was refluxed for 15 h during which time a white precipitate formed. The mixture was cooled to room temperature and the solution was carefully filtered under vacuum to isolate the precipitate but left unreacted in the reaction vessel. The precipitate was washed with water (100 ml) and dried in a vacuum oven. This solid was then recrystallized from the minimum amount of hot toluene (approximately 500 ml) to yield light yellow crystals of the 1:1 [9,9']Bianthracenyl/Toluene adduct (37 g, 81% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With hydrogenchloride; acetic acid; zinc; In water; at 80 - 90℃; for 8h;Inert atmosphere; | Implementation Example 1:; Add 600 ml glacial acetic acid, 25 g anthraquinone, and 55 g zinc powder in boiling flask-4-neck, fill it with nitrogen, heat and stir it. Drop 150 ml hydrochloric acid slowly while maintaining the temperature between 80 to 90. After that, react at 90, the color of the mixture is growing deep and solids are separated out gradually. After 8-hour reaction, no raw materials are left on tap, then stop the reaction, filtrate the solids and purify them with toluene, after drying them, 17 g products are gained with yield of 80%. m.p.>300; 1HNMR(CDCl3): 7.007.19 (m , 8 H), 7.427.48 (m , 4 H), 8.27 (d, J=12, 3 Hz, 4 H), 8.67(s, 2 H); ESIMS z/e: 355.1[M+H]+ |
80% | With hydrogenchloride; acetic acid; zinc; In water; at 80 - 90℃; for 8h;Inert atmosphere; | Add 600 ml glacial acetic acid, 25 g anthraquinone, and 55 g zinc powder in boiling flask-4-neck, fill it with nitrogen, heat and stir it. Drop 150 ml hydrochloric acid slowly while maintaining the temperature between 80 to 90. After that, react at 90, the color of the mixture is growing deep and solids are separated out gradually. After 8-hour reaction, no raw materials are left on the tap, then stop the reaction, filtrate and purify the solids with toluene, after drying them, 17 g products are gained with yield of 80%.m.p.>300;1HNMR (CDCl3): 7.007.19 (m,8H), 7.427.48 (m,4H), 8.27 (d, J=12, 3 Hz, 4H), 8.67 (s, 2H); ESIMS z/e: 355.1 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
37% | With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 0 - 20℃; for 5h;Darkness; | 9,9?-bianthracene (10 g, 28.2 mmol) was dissolved in DMF (200 mL), protected from light and N-bromosuccinimide (5.5 g, 31 mmol) diluted in DMF (20 ml) was added to the solution at 0 C. The reaction mixture was maintained at 0 C. for 1 hour. The solution was then warmed slowly to room temperature and stirred for 4 h. After the reaction completion, water was added to the mixture to terminate the reaction. The reaction mixture was extracted with ethyl acetate and water, dried with anhydrous magnesium sulfate, the solvent was removed and the residue was purified by column chromatography on silica(hexane-dichloromethane) to give product 4.5 g (37%) as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With N-Bromosuccinimide; In chloroform; at 20℃; | Preparation of Compound 3: Compound 1 (lg, 2.8 mmoL) was added to a three-necked flask,Dissolved in 100 mL of chloroform solventA 50 mL solution containing N-bromosuccinimide (1.2 g, 6.8 mmoL) was slowly added dropwise and stirred at room temperature for 3-8 h. Dichloromethane was extracted with solvent and the desiccant was dried over anhydrous magnesium sulfate, filtered, spin-dried, and purified with petroleum ether through a silica gel column to obtain 1.35 g of a solid in a yield of 95%. |
80% | With bromine; In 1,2-dichloro-ethane; at 20℃; for 4h;Product distribution / selectivity; | Add 5 g bianthryl, 80 ml 1,2-dichloroethane in 250 ml boiling flask-4-neck, then drop 5 g bromine, the solution turns red with no significant change of temperature. After addition of bromine, stir it for 4 hours at room temperature, a large amount of solid is separated out, filtrate and wash the solids with 20 ml 1,2-dichloroethane, 6.5 g product is gained with 80% of yield.m.p.>3001HNMR (CDCl3): 7.057.08 (m, 4H), 7.157.19 (m, 4H), 7.557.59 (m, 4H), 8.688.71 (m, 4H); ESIMS z/e: 510.9 [M+H]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 25℃; under 0.0750075 - 58805.9 Torr; for 1h;Kinetics; | 0.5897g of 9,9'-bianthryl (hereinafter, referred to as 'BA') in solid power state was evaluated according to the aforementioned test method under such a condition that the retention time at each pressure was 1 hour.. The relation between the balanced pressure and the hydrogen storage rate was shown in Table 3 and Fig. 3. From the results shown in Table 3 and Fig. 3, it was found that the hydrogen storage rate was increased as the hydrogen pressure was increased.. Even when the pressure was reduced from near 8 MPa, the storage rate is not lowered.. From this, it was found that the hydrogen storage is achieved not only by physical absorption.. This is attributed to the fact that hydrogen molecules are enclosed into the solid BA so as to form hydrogen clathrate. We confirmed that stored hydrogen can be emitted under condition of 50 C and the ambient pressure or under condition of a reduced pressure (0.005 MPa). |