Structure of 880800-19-1
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CAS No. : | 880800-19-1 |
Formula : | C30H24N2 |
M.W : | 412.53 |
SMILES Code : | C1(NC2=CC=C(C3=CC=CC=C3)C=C2)=CC=C(N(C4=CC=CC=C4)C5=CC=CC=C5)C=C1 |
MDL No. : | MFCD09878766 |
InChI Key : | BMWFGSBSRCFWTA-UHFFFAOYSA-N |
Pubchem ID : | 27281624 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 |
* 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 |
---|---|---|
81.5% | With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 120℃; for 10.0h;Inert atmosphere; | Combine 4-aminobiphenyl (8.2g, 48.5mmol), 4-bromotriphenylamine (15.7g, 48.5mmol),Sodium tert-butoxide (9.3g, 97mmol) was added to the reaction flask and replaced with nitrogen 3 times.Add toluene (100ml) under nitrogen protection, replace with nitrogen 3 times, add tris(dibenzylideneacetone) bispalladium (0.44g, 0.485mmol), 50% tri-tert-butylphosphine (0.39g, 0.97mmol) under nitrogen protection , Nitrogen replacement 3 times, heating to 120C and stirring for 10h. Cool to room temperature,Add 100ml of water and stir for 30min, suction and filter the solid to dry,The solid compound was separated and purified by column chromatography to obtain 16.3 g, 81.5%. |
73% | With sodium t-butanolate;tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); In toluene; for 2.0h;Heating / reflux; | 4-bromophenyl-N-phenyl-N-phenylamine (17.4 g, 53.7 mmol) and4-aminobiphenyl (9.99 g, 59.0 mmol) were dissolved in 250 ml of toluene, sodium- tertiary-butoxide (17.02 g, 177.1 mmol), bisdibenzylidene acetone palladium (0) (0.68 g, 1.2 mmol), and 50 wt% tri-tertiary-butylphosphine toluene solution (0.72 ml, 1.8 mmol) were added thereto, and reflux was conducted in a nitrogen atmosphere for 2 hours. Distilled water was added to the reaction solution to complete the reaction, and the organic layer was extracted. A column separation process was conducted using a solvent of n-hexane and tetrahydrofuran (n-hexane/THF = 10/1), stirring was conducted using petroleum ether, and vacuum drying was conducted to produce an arylamine connection group (16 g, yield 73%).[148] MS: [M+H]+= 412. |
73% | With tri-tert-butyl phosphine; sodium t-butanolate;bis(dibenzylideneacetone)-palladium(0); In toluene; for 2.0h;Inert atmosphere; Reflux; | Example 3Preparation of Compound Represented by Following Formula 2-4-4 1) Production of arylamine (4-(N-phenyl-N-phenylamino)phenyl-1-biphenylamine) to produce the compound represented by Formula 2-4-44-bromophenyl-N-phenyl-N-phenylamine (17.4 g, 53.7 mmol) and 4-aminobiphenyl (9.99 g, 59.0 mmol) were dissolved in 250 ml of toluene, sodium-tertiary-butoxide (17.02 g, 177.1 mmol), bisdibenzylidene acetone palladium (0) (0.68 g, 1.2 mmol), and 50 wt % tri-tertiary-butylphosphine toluene solution (0.72 ml, 1.8 mmol) were added thereto, and reflux was conducted in a nitrogen atmosphere for 2 hours. Distilled water was added to the reaction solution to complete the reaction, and the organic layer was extracted. A column separation process was conducted using a solvent of n-hexane and tetrahydrofuran (n-hexane/THF=10/1), stirring was conducted using petroleum ether, and vacuum drying was conducted to produce an arylamine connection group (16 g, yield 73%).MS: [M+H]+=412. |
66% | 4-aminobiphenyl (5.2 g, 31 mmol), 4-bromo-N, N-diphenylaniline, 10 g, 31 mmol), NaOtBu 4.5 g, 47 mmol) were placed in toluene (150 ml) and stirred under nitrogen. The reaction temperature was raised to 80 and reaction was carried out for 1 hour. Pd2 (dba) 3 (0.85 g, 0.93 mmol) and (tert-Bu) 3P (0.25 g, 1.24 mmol) were added thereto and reacted at 80 C for 4-5 hours. The reaction solution was filtered to remove the salt. The filtrate was distilled to remove toluene, and the concentrate was separated into a column to obtain Intermediate 1, and the yield was 8.4 g (yield: 66%). | |
60% | With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; tri tert-butylphosphoniumtetrafluoroborate; In toluene; at 90℃; for 19.0h;Inert atmosphere; | To a suspension of 17.8 g (55.0 mmol) of 4-bromo-N,N-diphenylaniline, 8.46 g (50.0 mmol) of [1,V-biphenyl]-4-amine, and 7.18g (74.7 mmol) of sodium tertbutanolate in 150 mL of toluene were added 0.29 g (1.00 mmol) of tri-tenbutyl35 phosphine tetrafluoroborate and 1 .04 g (1.00 mmol) of Pd2(dba)3 under an argonatmosphere. The mixture was heated at 90C for 19 h. After cooling, the mixture was added to 100 mL of half saturated aqueous NH4CI solution. The mixture was extended with 100 mL of ethyl acetate and the organic phase was separated. The aqueous phase was washed with ethyl acetate and the combined organic phases were washedwith saturated NaCI solution. The organic phase was separated, dried with MgSO4, and evaporated to dryness. The product was purified with column chromatography (cyclohexane/dichloromethane) to give the title compound as an off-white solid (12.4 g, 60%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With sodium t-butanolate;tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); In toluene; for 2.0h;Heating / reflux; | The compound of Formula b (4.7 g, 8.3 mmol) and4-(N-phenyl-N-phenylamino)phenyl-l-biphenylamine (7.9 g, 19.2 mmol) were dissolved in 150 ml of toluene, and sodium-tertiary-butoxide (5.53 g, 57.5 mmol), bisdibenzylidene acetone palladium(O) (0.22 g, 0.38 mmol), and 50 wt% tri- tertiary-butylphosphine toluene solution (0.23 ml, 0.58 mmol) were added thereto. After reflux was conducted in a nitrogen atmosphere for 2 hours, distilled water was added to the reaction solution to complete the reaction. The organic layer was extracted, and a column separation process was conducted using a solvent of n-hexane and tetrahydrofuran (n-hexane/THF = 4/1), stirring was conducted using petroleum ether, and vacuum drying was conducted to produce the compound of Formula 2-4-4 (4.9 g, yield 48%).[150] MS: [M+H]+= 1227. |
48% | With tri-tert-butyl phosphine; sodium t-butanolate;bis(dibenzylideneacetone)-palladium(0); In toluene; for 2.0h;Inert atmosphere; Reflux; | 2) The Compound of Formula b (4.7 g, 8.3 mmol) and <strong>[880800-19-1]4-(N-phenyl-N-phenylamino)phenyl-1-biphenylamine</strong> (7.9 g, 19.2 mmol) were dissolved in 150 ml of toluene, and sodium-tertiary-butoxide (5.53 g, 57.5 mmol), bis-dibenzylidene acetone palladium(0) (0.22 g, 0.38 mmol), and 50 wt % tri-tertiary-butylphosphine toluene solution (0.23 ml, 0.58 mmol) were added thereto. After reflux was conducted in a nitrogen atmosphere for 2 hours, distilled water was added to the reaction solution to complete the reaction. The organic layer was extracted, and a column separation process was conducted using a solvent of n-hexane and tetrahydrofuran (n-hexane/THF=4/1), stirring was conducted using petroleum ether, and vacuum drying was conducted to produce the compound of Formula 2-4-4 (4.9 g, yield 48%).MS: [M+H]+=1227. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide; water; In ortho-diethylbenzene; at 175℃; for 5.5h; | Under an atmospheric argon gas flow, blending 11.8 g of Intermediate 11, 16.8 g of 4-bromotriphenylamine, 414 mg of copper iodide, 6.2 g of potassium carbonate and diethylbenzene, the reaction was allowed to proceed at 175 C for 15 h. The resultant solution was cooled down and adding tap water, the residue was washed with acetone, methanol and tap water 3 times to obtain 20.4 g of benzamide compound of Intermediate 12. Blending 20.4 g of benzamide compound of Intermediate 12, 7.89 g of potassium hydroxide, 7.5 ml of tap water and diethylbenzene, the reaction was allowed to proceed at 175 C for 5.5 h. The resultant solution was cooled down and after adding tap water, it was filtered, washed with acetone, methanol and tap water 3 times. Purifying the resultant mixture by means of a short column (toluene), the resultant solid was washed with n-hexane and vacuum dried to obtain 9.65 g of yellowish white solid, which was analyzed by FD-MS and identified as Intermediate 12. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 110℃; for 3.0h;Inert atmosphere; | General procedure: 1.07 g of 0.01 mol of 3-methylaniline, 1.98 g of 0.01 mol of 4-bromoisopropylbenzene, and 3.1 g of sodium t-butoxide were added to a 100 ml three-necked flask, dissolved in 30 ml of toluene solution, and then 0.1 g of pd2 was added under nitrogen atmosphere. (dba) 3, 0.67 g of 10% tri-tert-butylphosphine, heating at 10 C, stirring for 3 hours, the reaction is complete, adding 25 ml of toluene, 25 ml of water, liquid separation, adding the organic phase column to silica gel spin-drying, column chromatography (solvent Ethyl acetate / petroleum ether = 1:20),The column was spun dry to give 1.7 g of white intermediate A2-1, yield 76%. |
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; potassium tert-butylate; In toluene; at 85℃; for 4.0h; | General procedure: 4-bromobiphenyl 4.66 g (20.0 mmol), 4-phenylaniline 5.07 g (30.0 mmol), Pd2(dba)3 0.37 g (0.4 mmol), PtBu3 0.08 g (0.4 mmol) and KOtBu2.88 g (30.0 mmol) ) After dissolving in 60 ml of toluene, it was stirred at 85 C. for 4 hours. After cooling the reaction solution to room temperature, it was extracted three times with 50 mL of water and 50 mL of diethyl ether. The organic layer obtained therefrom was dried over magnesium sulfate, and the residue obtained by evaporating the solvent was separated and purified through silica gel column chromatography to obtain an intermediate A-5 (5.65 g, 88% yield). The resulting compound was confirmed through MS/FAB. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | 1 (1.25 g, 3.1 mmol), 2 (1.03 g, 3.2 mmol) and NaOtBu (0.87 g, 18.3 mmol) were added to a 250 ml two-necked flask and stirred in nitrogen, and the reaction temperature was raised to 80 C And reacted for 1 hour. Pd2 (dba) 3 (0.08 g, 0.09 mmol) and (tert-Bu) 3P (0.03 g, 0.12 mmol) were added thereto and reacted at 80 C for 4-5 hours. The reaction solution is filtered to remove the salt. The filtrate was distilled to remove toluene and the concentrate was separated into a column to obtain DPAA-BP-pdC3, and the yield was 1.2 g (yield: 62%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | 1 (1.1 g, 2.6 mmol), 5 (1.05 g, 2.7 mmol) and NaOtBu (0.77 g, 7.9 mmol) were added to a 250 ml two-necked flask and stirred under nitrogen. Lt; 0 & gt; C and reacted for 1 hour. Pd (dba) 2 (0.05 g, 0.08 mmol) and (tert-Bu) 3P (0.02 g, 0.11 mmol) were added thereto and reacted at 80 C for 4-5 hours. The reaction solution was filtered to remove the salt. The filtrate was distilled to remove toluene, and the concentrate was separated into a column to obtain DPAA-BP-pdBeC3, and the yield was 1.1 g (yield: 62%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | 6 (1 g, 2.5 mmol), 1 (1 g, 2.4 mmol) and NaOt Bu (0.7 g, 7.3 mmol) were added to a 250 ml two-necked flask and the mixture was stirred under nitrogen and the reaction temperature was raised to 80 C React for 1 hour. Pd (dba) 2 (0.04 g, 0.07 mmol) and (tert-Bu) 3P (0.02 g, 0.1 mmol) were added thereto and reacted at 80 C for 4-5 hours. The reaction solution was filtered to remove saltsAll. The filtrate was distilled to remove toluene, and the concentrate was separated into a column to obtain DPAA-BP-BeFuP. The yield was 1 g(Yield: 60%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | 7(1.2 g, 2.9 mmol), 1 (1.1 g, 2.8 mmol) and NaOtBu (0.8 g, 8.4 mmol) were added to a 250 ml two-necked flask and the mixture was stirred under nitrogen and the reaction temperature was raised to 80 C And reacted for 1 hour. Pd (dba) 2 (0.05 g, 0.08 mmol) and (tert-Bu) 3P (0.03 g, 0.11 mmol) were added thereto and reacted at 80 C for 4-5 hours. The reaction solution was filtered to remove the salt. The toluene was removed by filtration, distilling the mixture, and separating the concentrated liquid into the column scored DPAA-BP-BeFuC3, the yield is 1.4g (yield: 65%) it was. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | 8 (1.15 g, 2.8 mmol), 1 (0.95 g, 3 mmol) and NaOtBu (0.8 g, 8.4 mmol) were added to a 250 ml two-necked flask, and the mixture was stirred under nitrogen and the temperature was raised to 80 C And reacted for 1 hour. Pd (dba) 2 (0.05 g, 0.08 mmol) and (tert-Bu) 3P (0.03 g, 0.11 mmol) were added thereto and reacted at 80 C for 4-5 hours. The reaction solution was filtered to remove the saltI will stay. The filtrate was distilled to remove toluene and the concentrate was separated into a column to obtain DPAA-BP-nPhaC3, and the yield was 1.2 g (yield: 65%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.67 g | With palladium diacetate; sodium t-butanolate; ruphos; In toluene; at 110℃; for 16.0h;Inert atmosphere; | 11.37 g (27.6 mmol) of N’-(4-biphenylyl)-N,N-diphenyl-1 ,4-benzenediamine, 3.82 g (12.5 mmol) of 5-chloro-3-(4-chlorophenyl)-1 ,1 ,3-trimethylindane, and 3.62 g (37.6 mmol) of sodium ten-butanolate were suspended in 150 mL of toluene under an argon atmosphere. To this suspension, 0.29 g (0.63 mmol) of RuPhos and 0.077 g (0.31 mmol) of palladium(ll) acetate were added. The mixture was heated at 110C for16 h. After cooling, the reaction mixture was poured on 300 mL of half saturated aqueous NH4CI solution. The organic phase was separated and the aqueous phase was extracted with ethyl acetate. The combined organic phases were washed with saturated NaCI solution, dried with MgSO4 and evaporated to dryness. The crude solid was purified with column chromatography (cyclohexane/dichloromethane) twice to givethe title compound as a yellowish solid (10.9 g, 82%). 1.98 g of the title compound were purified further by vacuum zone sublimation (1 Q-6 - 1 Q7 mbar, 270-320C) to give a yellowish solid (1 .67 g, purity >99.9% according to HPLC). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 120℃; for 10.0h;Inert atmosphere; | Intermediate 53-1 (16.3g, 39.5mmol), compound E: 4-(4'-chloro-[1,1':2',1”-terphenyl]-4-yl)dibenzo[b , D] Furan (17g, 39.5mmol), sodium tert-butoxide (7.6g, 79mmol) were added to the reaction flask, nitrogen replacement 3 times, toluene (100ml) was added under nitrogen protection, nitrogen replacement 3 times, nitrogen protection was added three times (Dibenzylideneacetone) bispalladium (0.36g, 0.395mmol), 50% tri-tert-butylphosphine (0.32g, 0.79mmol),Replace with nitrogen 3 times, heat up to 120C and stir for 10 hours. Cool to room temperature,Add 100ml of water and stir for 30min, suction and filter the solid to dry,20.3 g of solid compound was obtained by separation and purification by column chromatography with a yield of 64%. |
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