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CAS No. : | 60532-63-0 | MDL No. : | MFCD12546930 |
Formula : | C25H24N4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LNHGLSRCOBIHNV-UHFFFAOYSA-N |
M.W : | 380.49 | Pubchem ID : | 11825069 |
Synonyms : |
|
Num. heavy atoms : | 29 |
Num. arom. heavy atoms : | 24 |
Fraction Csp3 : | 0.04 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 4.0 |
Molar Refractivity : | 122.37 |
TPSA : | 104.08 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -5.61 cm/s |
Log Po/w (iLOGP) : | 2.18 |
Log Po/w (XLOGP3) : | 4.24 |
Log Po/w (WLOGP) : | 4.43 |
Log Po/w (MLOGP) : | 3.82 |
Log Po/w (SILICOS-IT) : | 3.53 |
Consensus Log Po/w : | 3.64 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -5.22 |
Solubility : | 0.0023 mg/ml ; 0.00000604 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -6.14 |
Solubility : | 0.000278 mg/ml ; 0.00000073 mol/l |
Class : | Poorly soluble |
Log S (SILICOS-IT) : | -8.5 |
Solubility : | 0.00000121 mg/ml ; 0.0000000032 mol/l |
Class : | Poorly soluble |
PAINS : | 1.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 2.54 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H319 | 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 |
---|---|---|
With sulfuric acid; water; sodium nitrite; at 0 - 50℃; | 400 g (1.05 mol) of the compound of Chemical Formula e is added to 1200 in of ultrapure water. The mixture is added to 320 ml of sulfuric acid while agitating it. Then, sodium nitrite is added thereto in a dropwise fashion at 0 C., and the resulting product is agitated at 50 C., obtaining tetrakis(p-hydroxyphenyl)methane (a compound of Chemical Formula f) (1H NMR (300 MHz, DMSO) delta 6.60 (d, 8H), 6.80 (d, 8H), 9.25 (s, 4H)). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; at 20℃; under 2.25023 - 3.0003 Torr; for 72h; | To a solution of tnpm (1.40 g, 2.95 mmol) in tetrahydrofuran (35 mL), Pd/C (10% Pd, catalytic amount) was added and the reaction mixture was purged with nitrogen for 10 min. The nitrogen gasin the reaction mixture was displaced by hydrogen gas to maintain the reducing atmosphere. Thereafter, the reaction mixture was stirred under hydrogen pressure (~3-4 mbar) at room temperature for 3 days. The reaction mixture was filtered over celite to remove Pd/C powder. The filtrate was dried to give tapm. as white powder. Yield: 96%. FTIR (ATR) (diamond crystal/ncm1): 3400, 3161, 3022, 1608, 1507, 1267, 803. 1H NMR (500 MHz,(CD3)2SO, d ppm): 6.67 (d, 8H, Ar-H), 6.38 (d, 8H, Ar-H), 4.85 (s,8H, -NH2); LC-MS (ESI Interface-positive ions): [MH]: found381.2063 (expected 381.2035). |
94% | With hydrogen;palladium 10% on activated carbon; In tetrahydrofuran; at 20℃; under 7500.75 Torr;Buchi reactor; | Compound 13 (8.8g, 17.6 mmol) and Pd on C (0.8g, 10%) were suspended in THF (500ml) in a Buchi hydrogenation apparatus. The apparatus was sealed, and 10 bar H2 was applied at ambient temperature. Reaction continued overnight under vigorous stirring. The reaction mixture was filtered through a celite pad. The pale yellow solution was evaporated on rotavapor to give compound 14 6.3g (94%) as a beige powder. The structure was confirmed by NMR. |
76% | With hydrazine hydrate;palladium on carbon; In butan-1-ol; at 50 - 60℃; for 2.5h;Inert atmosphere; | b. 4,4',4",4"'-methanetetrayltetraaniline To a 250 mL RB flask equipped with a magnetic stirrer and an oil- bath were added tetrakis(4-nitrophenyl)methane (6.50 g, 13.00 mmol), Pd/C (0.98 g, 15 wt%) and n-butanol (150 mL). With nitrogen bubbled through, the mixture was stirred and heated at 50 C for 15 min.Hydrazine hydrate ((7.6 mL, 156 mmol) was added dropwise via addition funnel while maintaining temperature at 50-60 C. The addition was finished in 30 min. After which, the reaction was stirred at 50 C for another 2 hr. The reaction remained heterogeneous throughout the time. HPLC analysis indicated all starting material had been consumed and the product appeared as the exclusive component. After cooling to RT, the mixture was purged with nitrogen for 10 min, then filtered and rinsed with THF. The solvent was removed by rotary evaporation and the residue was crystallized from ethanol to give product as light beige crystals, 3.76 g (76%). MS and NMR results are consistent with the structure proposed, |
72% | With hydrazine hydrate;Raney nickel; In tetrahydrofuran; for 4h;Inert atmosphere; Reflux; | Compound 3 was synthesized in a manner adopted from: Yang, X.; Loos, J.; Savenije, T. J.; Abellon, R. D.; Zuilhof, H.; Sudholter, E. J. R. J. Am. Chem. Soc. 2005, 127, 14530-14531. In particular, twenty (20) grams of Raney Ni were added to 3 grams of compound 2 (6 mmoles) dissolved in 200 mL of tetrahydrofuran (THF), while being stirred under nitrogen. To the reaction slurry, 4 grams of hydrazine hydrate (N2H4×H2O) was slowly added via syringe. The reaction was refluxed for 4 hours, and then filtered while hot. The solid residue was washed with ethanol, and all filtrate fractions were combined and dried in vacuo. The crude product was washed with ethanol (100 mL) to afford analytically pure 3 as white solid (1.65 grams, 72%). 1H NMR (300 MHz, d6-DMSO, 25 C.): delta 6.63 (d, 8H), delta 6.34 (d, 8H) delta 4.81 (bs, 8H); 13C {1H} NMR (75.5 MHz, d6-DMSO, 25 C.): delta 146.3 (s), 136.5 (s), 131.7 (s), 113.1 (s), delta 61.8 (s). |
With hydrogen;palladium on activated charcoal; In ethanol; for 30h; | Then, 4500 ml of tetrahydrofuran is added in a hydrogenizing reactor, and 450 g (0.89 mol) of the compound of Chemical Formula d is added thereto. On the other hand, 90 g of a palladium/carbon catalyst is added to 1200 ml of ethanol. This mixture is slowly added to the reactor. The resulting product is agitated for 30 hours while hydrogen gas is continuously injected into the reactor. Then, it is washed with ethanol and n-hexane and dried, obtaining 295 g of a compound of Chemical Formula e (1H NMR (300 MHz, DMSO) delta 4.83 (s, 8H), 6.37 (d, 8H), 6.66 (d, 8H)). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Na2CO3; In acetone; | EXAMPLE D Synthesis of Tetrakis [4[(2,4-dichloro-1,3,5-triazin-6-yl)amino]phenyl]methane A solution of <strong>[60532-63-0]tetrakis(4-aminophenyl)methane</strong> (4.57 grams, 12.0 mmol; prepared as described in Example C) in acetone (96 milliliters) was added dropwise at 0 C to a stirred solution of cyanuric chloride (9.06 grams, 49.1 mmol; obtained from Aldrich Chemical Co., Milwaukee, Wis.) in acetone (144 milliliters). The resulting mixture was kept at 0 C. for 1 hour, treated with Na2CO3 (5.21 grams, 49.2 mmol), and poured into water (960 milliliters). The precipitate was separated by filtration, washed with water, and dried to give the tetrakis[4-[(2,4-dichloro-1,3,5-triazin-6-yl)amino]phenyl]methane (7.97 grams, 8.20 mmol, 68 percent yield) as a colorless solid: mp >310 C.; 1H NMR (400 MHz, DMSO-d6, 25 C.) delta7.18 (d, 8H, 3J=8.7 Hz), 7.55 (d, 8H, 3J=8.7 Hz), 11.18 (s, 4H); 13C NMR (75.4 MHz, DMSO-d6, 25 C.) delta64.1, 121.7, 131.7, 135.8, 143.8, 164.6, 169.7, 170.7; MS (FAB, 2-nitrobenzyl alcohol) m/e 969. Anal. Calcd for C37H20Cl8N16: C, 45.71; H, 2.07; N, 23.05. Found: C, 46.03; H, 2.09; N, 22.61. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE C Synthesis of Tetrakis(4-aminophenyl) methane In a Parr reactor, tetrakis(4-nitrophenyl)methane (17.0 grams, 34.0 mmol; prepared as described in Example B) and palladium, 10 weight percent on activated carbon (2.15 grams, 2.00 mmol; obtained from Aldrich Chemical Co., Milwaukee, Wis.) were added to tetrahydrofuran (450 milliliters). The reactor was closed, and the mixture was stirred under 200 pounds per square inch (13.6 atmospheres) of hydrogen pressure for 72 hours at room temperature. The mixture was then filtered through CELITE, solvent was removed from the filtrate by evaporation under reduced pressure, and the resulting white solid was triturated in chloroform. The solid was then recovered by filtration, washed with chloroform again, and dried under reduced pressure at room temperature to give the targeted tetrakis(4-aminophenyl)methane as a white powder in a quantitative yield (12.9 grams). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; In toluene; at 80℃; for 42h; | c. N,N,,N",N"'-(4,4,,4",4,"-methanetetrayltetrakis(benzene-4, 1 - diyl))tetrakis(2,4,5-trimethyl-N-(2,4,5-trimethylphenyl)aniline) In a dry box, 4,4',4",4"'-methanetetrayltetraaniline (1 .00 g, 3.08 mmol), 1 - <strong>[5469-19-2]bromo-2,4,5-trimethylbenzene</strong> (1 .35 g, 3.67 mmol), tris(tert- butyl)phosphine (0.1 0 g, 0.50 mmol) and Pd2(DBA)3 (0.23 g, 0.25 mmol) were combined in round bottom flask and dissolved in 120 ml of dry toluene. The solution was stirred for a minute and followed by sodium tert- butoxide (2.72 g, 28.33 mmol) and 5 ml of dry toluene. A heating mantle was added and the reaction heated to 80C for 18 hour. More 1 -bromo- 2,4,5-trimethylbenzene (350mg) and NaOtBu (180mg) were added and the reaction stirred at 80C for another 24 hour. The reaction mixture was then cooled to room temperature and filtered, washing with toluene (200 mL). The solvent was removed by rotary evaporation and the residue was re-dissolved in chloroform (40ml_). The crude product was precipitated into methanol (300ml_) and collected (3.3g, 85% pure) by filtration. The crude product was purified further by silica gel column chromatography using a gradient of chloroform in hexanes (5-21 %). Recrystallization from chloroform and ethanol yielded 2.60 g (64%) of product as a pale yellow solid. 1 H NMR (CDCI3) is consistent with structure for Compound 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | Dissolve 2-(Ethoxycarbonyl)-tetrathiafulvalene (8, 110mg, 0.4mmol) in 15mL of THF, to which 5mL of 0.1M NaOH aqueous solution was added. The mixture was stirred at room temperature until all of the compound 8 was consumed. Then 0.5M of HCl aqueous solution was added dropwisely until pH 7. The mixture was extracted by dichloromethane and washed by 2×50mL of water. The organic layer was dried over anhydrous MgSO4 and the solvent was removed under vacuum. To the residue dissolved in 10mL of DMF were added EDCI (87mg, 0.45mmol), DMAP (55mg, 0.45mmol), and <strong>[60532-63-0]tetrakis(4-amino-phenyl)methane</strong> (6, 19mg, 0.05mmol) subsequently. The mixture was stirred at room temperature for 5 days and the solvent was removed under vacuum, the residue was recrystallized from dichloromethane to give T2 (31mg) in 48% yield as a red solid. FT-IR (nu) 3070, 2975, 2923, 2360, 1637, 1596, 1508, 1405, 1322cm-1; 1H NMR (400MHz, DMSO-d6) delta 10.33 (s, 4H), 7.83 (s, 4H), 7.55 (d, J=8.0Hz, 8H), 7.07 (d, J=8.0Hz, 8H), 6.75 (s, 8H); 13C NMR (100MHz, DMSO-d6) delta 157.4, 142.0, 139.1, 136.1, 133.8, 130.6, 126.9, 120.3, 120.0, 119.4, 112.5, 107.0, 105.8, 42.0; HRMS (ESI): calcd for 1/2 (C53H32N4O4S16), 649.8977 [M]2+, found: 649.8986. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With acetic acid In water; 1,2-dichloro-benzene; butan-1-ol at 120℃; for 72h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With acetic acid In ethyl acetate; 1,3,5-trimethyl-benzene at 20℃; for 48h; |
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