Structure of 3842-55-5
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Cyniak, Jakub S. ; Kasprzak, Artur ;
Abstract: The synthesis of two novel aromatic dendrimers structurally derived from 1,3,5-tri[1,3-diphenyl(phenyl-5-yl)phenyl-4'-yl]benzene and bearing 2,4,6-triphenyl-1,3,5-triazine cores is reported. The obtained dendrimers were used for the OLEDs construction, as well as in the role of innovative photocatalysts for the very efficient and selective oxidation of various benzylamines to resp. N-benzylidene benzylamines under mild conditions.
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CAS No. : | 3842-55-5 |
Formula : | C15H10ClN3 |
M.W : | 267.71 |
SMILES Code : | ClC1=NC(C2=CC=CC=C2)=NC(C3=CC=CC=C3)=N1 |
MDL No. : | MFCD05738885 |
InChI Key : | DDGPPAMADXTGTN-UHFFFAOYSA-N |
Pubchem ID : | 19698 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 19 |
Num. arom. heavy atoms | 18 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 75.71 |
TPSA ? Topological Polar Surface Area: Calculated from |
38.67 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
3.28 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
4.26 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.86 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.03 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
4.08 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.7 |
Log S (ESOL):? ESOL: Topological method implemented from |
-4.75 |
Solubility | 0.00473 mg/ml ; 0.0000177 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-4.78 |
Solubility | 0.0044 mg/ml ; 0.0000164 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-6.93 |
Solubility | 0.0000314 mg/ml ; 0.000000117 mol/l |
Class? Solubility class: Log S scale |
Poorly soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
Yes |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
Yes |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
Yes |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
Yes |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
Yes |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-4.91 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
0.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.15 |
* 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 hydrogenchloride;aluminium trichloride; In 5,5-dimethyl-1,3-cyclohexadiene; | EXAMPLE 19 2-(2,4-Dihydroxy-5-hexylphenyl)-4,6-diphenyl-s-triazine To a 350 mL sulfonation flask equipped with a mechanical stirrer, condenser and a nitrogen atmosphere are charged 21.4 g (80 mmol) of 2-chloro-4,6-diphenyl-s-triazine, and 100 mL of xylene (mixture of isomers). To the beige suspension are added 11.3 g (85 mmol) of aluminum chloride in one portion. The mixture is warmed to ca. 80 C. for 45 minutes. 18.8 g (96 mmol) of 4-hexylresorcinol are then added in five portions over 40 minutes to the now homogeneous solution. The reaction mixture is heated at 90 C. for 24 hours. After cooling to room temperature, the contents of the flask are poured into 100 mL of 12% aqueous hydrochloric acid. The precipitate formed is removed by filtration, washed to pH 7 with water, rinsed with methanol and dried at 70 C. under vacuum. The title compound is obtained as a crude orange product (29.2 g) and melts at 209-213 C. It can be used without further purification. | |
With hydrogenchloride;aluminium trichloride; In 5,5-dimethyl-1,3-cyclohexadiene; | Example 19 2-(2,4-Dihydroxy-5-hexylphenyl)-4,6-diphenyl-s-triazine To a 350 mL sulfonation flask equipped with a mechanical stirrer, condenser and a nitrogen atmosphere are charged 21.4 g (80 mmol) of 2-chloro-4,6-diphenyl-s-triazine, and 100 mL of xylene (mixture of isomers). To the beige suspension are added 11.3 g (85 mmol) of aluminum chloride in one portion. The mixture is warmed to ca. 80 C. for 45 minutes. 18.8 g (96 mmol) of 4-hexylresorcinol are then added in five portions over 40 minutes to the now homogeneous solution. The reaction mixture is heated at 90 C. for 24 hours. After cooling to room temperature, the contents of the flask are poured into 100 mL of 12% aqueous hydrochloric acid. The precipitate formed is removed by filtration, washed to pH 7 with water, rinsed with methanol and dried at 70 C. under vacuum. The title compound is obtained as a crude orange product (29.2 g) and melts at 209-213 C. It can be used without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | Synthesis of Comparative Compound 1. 3,6-Diphenyl-9H-carbazole (4.00 g, 12.52 mmol) was dissolved in anhydrous DMF (170 mL) and treated with NaH (0.751 g, 18.79 mmol, 60percent dispersion in mineral oil) while stirring vigorously at room temperature providing yellow solution. Once H2 evolution stopped, the solution was stirred for 1 hour, and then treated with 2-chloro-4,6-diphenyl-1,3,5-triazine (5.03 g, 18.79 mmol), and left stirred overnight at room temperature. After stirring for ?30 minutes, reaction solution had significant white precipitate swirling around. The crude mixture was quenched with water and filtered. The white precipitate was washed with water, MeOH, and EtOH. The material was recrystallized from toluene (400 mL) to obtain the target, Comparative Compound 1 with 99.86percent purity. One more recrystallization from toluene gave a purity of 100percent to afford 6.0 g (87percent yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42.96% | With sodium hydride; In N,N-dimethyl-formamide; at 20℃; for 12h; | Compound 17-2 (5g, 17.64mmol) and 2-Chloro-4,6-diphenyltriazine (5.6g, 21.17mmol) were dissolved in DMF (100ml). NaH (1.05g, 26.46mmol) was slowly added thereinto, followed by stirring at room temperature for 12 hours. Distilled water was added thereinto, and the solids were filtered under reduced pressure, followed by column chromatography, thereby obtaining Compound 95 (3.9g, 42.96%). MS/FAB found 514, calculated 514.62 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | 3-(9-carbazolyl) carbazole (3.8g) under nitrogen dissolved in 60 ml dry N, N '-dimethyl formamide. Adding 0.7g of sodium hydride, and stirring at room temperature 1 hour. N then dissolved in dry, N '-dimethyl formamide in the 2-chloro -4, 6 diphenyl -1, 3, 5-triazine (U-1, 3.6g) solution (25 ml) is added to the reaction mixture. The reaction further stirring 3 hours. In water is poured into the reaction mixture, to precipitate the product. Then with methanol-hexane for cleaning solid, and drying under vacuum, in order to obtain 5.4g of the 2, 4-diphenyl-6-(-carbazolyl 3-N) carbazole -9 the [...] -yl)-1, 3, 5-triazine, i.e. compound 2-1 (84%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 80℃; for 20h;Inert atmosphere; | In the nitrogen ambient, after the compound 1-120 g (56.5 mmol) was melted in the tetrahydrofuran (THF) 0.2 L here 2- chloro-4,6- diphenyl -1,3,5- triazine (2-chloro-4,6-diphenyl-1,3,5-triazine) 15.1 g(56.5 mmol) and tetrakis (triphenylphosphine) palladium(tetrakis(triphenylphosphine)palladium) 0.65 g (0.57 mmol) were put and itmixed. The saturated potassium carbonate 19.5 g (141 mmol) was put in water andit heated up in 80 for 20 hours and it refluxed. After water was put ininto the reaction solution after the reaction completion and it extracted inthe dichloromethane (DCM) moisture was removed to the anhydrous MgSO4 it filteredand it was concentrated under reduced pressure. The residue obtained in thisway was refined to the flash column chromatography after dividing and compoundA - 1s (22.1 g, 85 %) were obtained |
85% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 80℃; for 20h;Inert atmosphere; | Dissolve 20 g of the above mentioned compound 1-1 (56.5 mmol) in tetrahydrofuran (THF) in a nitrogen environment, 0.2 L, here the 2-chloro-4,6-diphenyl-1,3,5-triazine (2 chloro-4-diphenyl-,6-1 ,3,5-triazine) 15.1 g (56.5 mmol) and tetrakis (triphenylphosphine) palladium (tetrakis (triphenylphosphine) palladium) 0.65 g (0.57 mmol) and the mixture was stirred .Into a potassium carbonate 19.5 g (141 mmol) in saturated water it was heated to reflux at 80 for 20 hours.After the reaction was completed, the reaction solution into water, extracted with dichloromethane (DCM) and then water was removed with anhydrous MgSO4, filter and was concentrated under reduced pressure.Thus the resulting residue was separated and purified by flash column chromatography to give the compound A-1 (22.1 g, 85%). |
85% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 80℃; for 20h;Inert atmosphere; | Under a nitrogen atmosphere, 20 g (56.5 mmol) of Intermediate 1-1 was dissolved in 0.2 liters (L) of tetrahydroffiran (THF), and 15.1 g (56.5 mmol) of 2-chloro-4,6- diphenyl-1,3,5-triazine and 0.65 g (0.57 mmol) of tetrakis (triphenylphosphine)palladium were added thereto and the reaction mixture was agitated. 19.5 g (141 mmol) of potassium carbonate saturated in water was added thereto, and the resultant was heated at a temperature 80 C. for 20 hours under reflux. Afier the reaction was completed, water was added to the reaction solution and the mixture was extracted by using dichloromethane (DCM). Then, an anhydrous magnesium sulfate (MgSO4) was added thereto to perform dehydration. The resultant was filtered and concentrated under reduced pressure. The obtained residual was separated and purified by flash column chromatography to obtain 22.1 g (85%) of Compound A-1 HRMS (70 eV, EI+): m/z calcd for C33H21N3:459.1735, found: 459. Elemental Analysis: C, 86%; H, 5% |
85% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 80℃; for 20h;Inert atmosphere; | 20 g (56.5 mmol) of Compound 1-1 was dissolved in 0.2 L of tetrahydrofuran (THF) under a nitrogen condition (a nitrogen atmosphere), and 15.1 g (56.5 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine and 0.65 g (0.57 mmol) of tetrakis(triphenylphosphine)palladium were added thereto. The mixed solution was then stirred. 19.5 g (141 mmol) of potassium carbonate saturated in water was added thereto, and refluxed by a heating process performed thereon at a temperature of 80 C. for 20 hours. After the reaction was completed, water was added to the reaction solution, and an extraction process was performed thereon by using dichloromethane (DCM). Moisture in the extraction was dried by using anhydrous magnesium sulfate (MgSO4), and the resulting mixture was then filtered and concentrated under reduced pressure. The residue obtained therefrom was separated and purified by flash column chromatography to obtain 22.1 g (85%) of Compound A-1. (0439) HRMS (70 eV, EI+): m/z calcd for C33H21N3: 459.1735, found: 459. (0440) Elemental Analysis: C, 86%; H, 5% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
<Reaction Scheme 2> In the reaction vessel, <strong>[117635-21-9]1,4-dibromo-2,5-dihexylbenzene</strong> (0.81 g, 2.0 0 mmol),20 ml of tetrahydrofuran was added, and at -78 C.,The mixture was stirred. Thereafter, 1.6 M n-butyllithium (n-BuLi) hexane solution (2.53 ml, 4.00 mmol) was added dropwise and after stirring for 1 hour, 3,5-diphenyl- 1-chlorotriazine was added , And the mixture was stirred at room temperature for 3 hours.After completion of the reaction, water was added to the reaction mixture,The mixture was extracted with chloroform, and the organic layer was concentrated. after that,Tetrahydrofuran was added to and dissolved in the resulting residue,Purification was carried out by reprecipitation twice using methanol to obtain a compound B. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydride; In N,N-dimethyl-formamide; at 80℃; for 12h;Inert atmosphere; | Dissolve E10-1 (30.0 g), 2-chloro-4,6-diphenyl-1,3,5-triazine (27.1 g) and NaH (3.2 g) in 400 ml of dry DMF under a nitrogen atmosphere Reaction at 80 C for 12h.After cooling, slowly add a small amount of water, remove the solvent by rotary evaporation, extract with dichloromethane and wash and separate the solution with water.Column chromatography and recrystallization gave Intermediate E10-2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In tetrahydrofuran; water; at 2080.0℃; for 20.0h;Inert atmosphere; | <strong>[1092485-88-5]3,5-dichloro-4-fluorophenyl boronic ester</strong> (1.00 equivalents; CAS 1092485-88-5), 2-chloro-4,6-diphenyl-1,3,5-triazine (1.1 equivalents), Pd(dppf)2Cl2 (0.05 equivalent), and potassium acetate (3.00 equivalents) are stirred under nitrogen atmosphere in a THF/water mixture (ratio of 10:1) at 80 C. for 20 h. The cooled mixture is poured into brine, the precipitated product is filtered off and washed with water and cold ethanol. The product E1-1 is obtained as a solid. |