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Chemical Structure| 15424-38-1 Chemical Structure| 15424-38-1

Structure of 15424-38-1

Chemical Structure| 15424-38-1

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Product Details of [ 15424-38-1 ]

CAS No. :15424-38-1
Formula : C20H15N
M.W : 269.34
SMILES Code : C12=CC=CC=C1C(NC3=CC=CC=C3)=C4C=CC=CC4=C2
MDL No. :MFCD03093237
InChI Key :VNXLMMFDPYSZKF-UHFFFAOYSA-N
Pubchem ID :13777361

Safety of [ 15424-38-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 15424-38-1 ]

* 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.

  • Downstream synthetic route of [ 15424-38-1 ]

[ 15424-38-1 ] Synthesis Path-Downstream   1~32

YieldReaction ConditionsOperation in experiment
83.9% With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate; In cyclohexane; toluene; for 2h;Inert atmosphere; Reflux; General procedure: Step 1: Synthesis of 3,5-dimethyl-N-phenylaniline (S2)Under nitrogen, in a 500ml three-necked round flask, add 15.7g (0.1mol) of bromobenzene, 13.3 g (0.11mol) 3,5-dimethylaniline, 0.57g (1.0mol%) Pd (dba)2 , 2.0 ml (1.0mol%) P(t-Bu)3 10% cyclohexane solution and 19.2g (0.2mol)NaO(t-Bu). Followed by addition of 250ml anhydrous toluene, to obtain a reaction solution. The said reaction solution under magnetic stirring in a 110deg.C oil bath was refluxed for 2h. Cool. Then the reaction solution was washed with water and an appropriate amount of 2-3 times after subjected to liquid separation, and the resulting organic phase was dried over anhydrous MgSO4, the organic solvent was removed by rotary evaporation to give crude product. The crude product was purified by silica gel (200-300 mesh, Qingdao Marine Chemical) column chromatography to give the product 16.1g, a yield of 81.6%.
  • 6
  • [ 15424-38-1 ]
  • [ 380149-52-0 ]
  • <i>N</i>5,<i>N</i>5'-di-anthracen-9-yl-3,3',<i>N</i>5,<i>N</i>5'-tetraphenyl-[2,2']bithiophenyl-5,5'-diamine [ No CAS ]
  • 7
  • [ 573-17-1 ]
  • [ 15424-38-1 ]
  • (anthracen-9-yl)(phenanthren-9-yl)phenylamine [ No CAS ]
  • 8
  • [ 1564-64-3 ]
  • [ 62-53-3 ]
  • [ 15424-38-1 ]
YieldReaction ConditionsOperation in experiment
86% With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; XPhos; In toluene; at 100 - 110℃; for 2h;Inert atmosphere; (1) To mechanical agitation, thermometer, After replacing the three-port reaction flask in the condenser with nitrogen, Add intermediate 24a (100mmol) in sequence, Raw material 24b (95mmol), 300ml toluene, heated to reflux for 0.5h, Cool down to 70 - 80 C, Slowly add sodium tert-butoxide (150mmol), Pd2 (dba) 3 (0.25mmol), xphos (0.5mmol), After the system is stable, it is heated to 100 - 110 C for 2 hours. Reduce the temperature to 25 - 30 C, add 200ml of water, stir and separate with 100ml of toluene, and extract the aqueous phase once with 200ml of toluene. Separate the liquid, combine the organic phase, add 7g of anhydrous sodium sulfate to the organic phase, stir and dry, filter The organic phase is concentrated (-0.08-0.09MPa, 55-60 C ) so that Recrystallize with 60ml toluene, filter, 82 mmol of intermediate 24c was obtained with a yield of 86%.
70% With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate; In toluene; at 100℃; for 72h;Inert atmosphere; Sealed tube; An oven-dried pressure tube was cooled under nitrogen and charged with 9-bromanthracene (0.5 g, 1.9 mmol), distilled aniline (0.26 mL, 2.9 mmol), NaOtBu (0.44 g, 3.8 mmol), Pd(OAc)2 (22 mg, 5 mol%) and P(tBu)3 (23 uL, 0.1 mmol). To this was added dry toluene (10 mL). The pressure tube was sealed under nitrogen and stirred at 100 C for 72 h. After 72 h, the pressure tube was cooled to rt and toluene was removed in vacuo. Subsequently, the reaction was quenched with water and the organic contents were extracted with chloroform. The combined extract was dried over anhyd Na2SO4 and filtered. The solvent was removed in vacuo and the crude product was subjected to silica gel column chromatography using CHCl3/pet.ether (5:95) as an eluent to yield pure 9-(N-phenylamino)anthracene as yellow crystalline solid (0.36 g, 70% yield); mp 145 C; IR (neat film) cm1 3392, 1601, 1499, 1421, 1355, 1307; 1H NMR (CDCl3, 500 MHz) d 5.99 (s,1H), 6.59 (d, J = 8.0 Hz, 2H), 6.78 (t, J = 6.8 Hz, 1H), 7.14(t, J = 7.4 Hz, 2H), 7.44-7.48 (m, 4H), 8.05 (d, J = 8.6 Hz,2H), 8.19 (d, J = 8.6 Hz, 2H), 8.41 (s, 1H); 13C NMR (CDCl3, 125 MHz) d 113.8, 118.4, 123.8, 125.3, 125.4, 125.8,128.7, 129.0, 129.2, 132.2, 132.4, 147.9; EI-MS+ m/z Calcdfor C20H15N 269.1204 [M+], found 269.1206.
  • 9
  • [ 1564-64-3 ]
  • [ 103-84-4 ]
  • [ 15424-38-1 ]
  • 10
  • [ 866413-65-2 ]
  • [ 15424-38-1 ]
  • [ 948305-21-3 ]
  • 11
  • [ 81-86-7 ]
  • [ 15424-38-1 ]
  • 4-(phenyl anthracen-9-yl)amino-1,8-naphthalic anhydride [ No CAS ]
  • 12
  • [ 15424-38-1 ]
  • [ 948309-27-1 ]
  • 13
  • [ 15424-38-1 ]
  • (E)-3-(5-(7-(anthracen-9-yl(phenyl)amino)-9,9-diethyl-9H-fluoren-2-yl)thiophen-2-yl)-2-cyanoacrylic acid [ No CAS ]
  • 16
  • [ 10386-84-2 ]
  • [ 15424-38-1 ]
  • 4-bromo-4'-[N-(9-anthracenyl)-N-phenylamino]-2,2',3,3',5,5',6,6'-octafluoro-1,1'-biphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
In a nitrogen flow, 160 mg (0.282 mmol) of palladium bis (benzylideneacetone) and 170 mg (0.846 mmol) of tri-tert-butylphosphine were dissolved in 40 ml of toluene and then stirred for 15 minutes at room temperature. Then, 0.58 g (1.27 mmol) of 4,4'- [ F] [DIBROMO-2, 2',] 3, [3',] 5, 5', 6, [6'-OCTAFLUORO-1,] 1'-biphenyl dissolved in 50 ml of toluene was dropped into the mixture and it was stirred for 30 minutes. Furthermore, 0.34 g (1.27 mmol) of [N- (9-ANTHRACENYL)-] N-phenylamine was dissolved in 50 ml of toluene and was then dropped therein, followed by the addition of 0.18 g (1.91 mmol) of sodium tert-butoxide. Then, the mixture was heated and stirred for about 8 hours in an oil bath heated at [120C.] After returning the reaction solution to room temperature, 50 ml of water was added thereto and the resultant solution was then separated into an aqueous layer and an organic layer. Furthermore, the aqueous layer was extracted with toluene and ethyl acetate, and was then combined with the previous organic layer and dried with magnesium sulfate. The solvent was evaporated and then the residue was purified by silicagel-column chromatography (toluene : hexane = [1 :] 2) to obtain 0.55 g of [4-BROMO-4'-[N-(9-ANTHRACENYL)-N-] [PHENYLAMINO]-2,] 2', 3, 3', 5, 5', 6, [6'-OCTAFLUORO-1,] 1'- biphenyl.
  • 17
  • [ 327061-54-1 ]
  • [ 15424-38-1 ]
  • [ 1255517-95-3 ]
  • 18
  • C23H18N2O2 [ No CAS ]
  • [ 15424-38-1 ]
  • 19
  • [ 15424-38-1 ]
  • [ 1042269-05-5 ]
  • C55H40N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate; In toluene; at 100℃; for 72h;Inert atmosphere; Sealed tube; General procedure: An oven-dried pressure tube was cooled under nitrogen and charged with 9-bromanthracene (0.5 g, 1.9 mmol), distilled aniline (0.26 mL, 2.9 mmol), NaOtBu (0.44 g, 3.8 mmol), Pd(OAc)2 (22 mg, 5 mol%) and P(tBu)3 (23 uL, 0.1 mmol). To this was added dry toluene (10 mL). The pressure tube was sealed under nitrogen and stirred at 100 C for 72 h. After 72 h, the pressure tube was cooled to rt and toluene was removed in vacuo. Subsequently, the reaction was quenched with water and the organic contents were extracted with chloroform. The combined extract was dried over anhyd Na2SO4 and filtered. The solvent was removed in vacuo and the crude product was subjected to silica gel column chromatography using CHCl3/pet.ether (5:95) as an eluent to yield pure 9-(N-phenylamino)anthracene as yellow crystalline solid (0.36 g, 70% yield)
  • 20
  • [ 108-86-1 ]
  • [ 779-03-3 ]
  • [ 15424-38-1 ]
YieldReaction ConditionsOperation in experiment
80% With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate; In toluene; for 2h;Reflux; The tri-butyl phosphine (4.4 ml of 1.0M toluene solution, 1.48g, 0 . 05mmol), palladium acetate (0.4g, 1 . 83mmol) butyl sodium (22.8g, 238mmol) added to the 9 - amino anthracene (35.3g, 183mmol) and bromobenzene (59.9g, 183mmol) in degassing toluene (500 ml) of the solution in a, and the mixture is heated to reflux 2 hours. The reaction mixture is cooled to room temperature, the toluene dilution and for via the diatomaceous earth filter. The filtrate diluted with water, and is extracted with toluene, and combined with the organic phase, and under the condition of vacuum evaporation. The residue through silica gel (heptane/dichloromethane) filter, and from the isopropanol in crystallization. To obtain 1 - 4 (39.3g, the theoretical value of 80%).
80% With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate; In toluene; for 2h;Reflux; A solution of tri-tert-butylphosphine (4.4 mL of 1.0 M in toluene, 1.48 g, 0.05 mmol)Palladium acetate (0.4 g, 1.83 mmol)And sodium tert-butoxide (22.8 g, 238 mmol)Was added to 9-aminanthracene (35.3 g, 183 mmol)And bromobenzene (59.9 g, 183 mmol)In degassed toluene (500 mL)And the mixture was heated under reflux for 2 hours.The reaction mixture was cooled to room temperature,Diluted with toluene and filtered through diatomaceous earth.The filtrate was diluted with water,And extracted with toluene,And the organic phase is combined,It was evaporated under vacuum.The residue was filtered through silica gel (heptane / dichloromethane)And crystallized from isopropanol.A2 (39.3 g, 80% theoretical).
  • 21
  • [ 109-04-6 ]
  • [ 15424-38-1 ]
  • C25H18N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With palladium diacetate; sodium t-butanolate; In toluene; for 2h;Reflux; The tri-butyl phosphine (4.4 ml of 1.0M toluene solution, 1.13g, 5 . 6mmol), palladium acetate (0.3g, 1 . 4mmol) butyl sodium (40.3g, 420mmol) added to the 1 - 4 (37.6g, 140mmol) and 2 - 1 (34.4g, 168mmol) in degassing toluene (500 ml) of the solution in a, and the mixture is heated to reflux 2 hours. The reaction mixture is cooled to room temperature, the toluene dilution and for via the diatomaceous earth filter. The filtrate diluted with water, and is extracted with toluene, and combined with the organic phase, and under the condition of vacuum evaporation. The residue through silica gel (heptane/dichloromethane) filter, and from the isopropanol in crystallization. The resulting solid 1 - 5 (46.3g, 134mmol) and NBS (28.6, 161mmol) is dissolved in DMF with chloroform (1:3, 60 ml) in the mixed solution of, the room temperature stirring 6 hours, water and dichloromethane is used for extraction, drying the organic phase, concentration and crystallization from isopropanol in the obtained intermediate A2 (47.6g, the theoretical value of 80%).
With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate; In toluene; for 2h;Reflux; Tri-tert-butylphosphine (4.4 mL of 1.0 M in toluene, 1.13 g, 5.6 mmol)Palladium acetate (0.3 g,1.4 mmol) and sodium tert-butoxide (40.3 g, 420 mmol)Was added to A2 (37.6 g, 140 mmol)And 2-bromopyridine (34.4 g, 168 mmol)In degassed toluene (500 mL)And the mixture was heated under reflux for 2 hours.The reaction mixture was cooled to room temperature,Diluted with toluene and filtered through diatomaceous earth.The filtrate was diluted with water,And extracted with toluene,And the organic phase is combined,It was evaporated under vacuum.The residue was filtered through silica gel (heptane / dichloromethane)And crystallized from isopropanol.The resulting solid B2 (46.3 g, 134 mmol) and NBS (28.6, 161 mmol)Was dissolved in DMF and chloroform (1: 3, 60 mL)Of the mixed solution,Stir at room temperature for 6 hours,Add water and extract with methylene chloride,Drying the organic phase,Concentration and crystallization from isopropanol gave Intermediate C2 (47.6 g, 80% of theory).
  • 22
  • [ 17135-78-3 ]
  • [ 15424-38-1 ]
  • C34H23N [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate; In toluene; for 2h;Reflux; Tri-tert-butylphosphine (3 mL of a 1.0 M solution in toluene, 7.32 mmol), palladium acetate (0.4 g, 1.83 mmol) and sodium tert- butoxide (52.7 g, 549 mmol) were added to 2- chloroanthracene ) And Intermediate A-1 (49.2 g, 183 mmol) in degassed toluene (500 mL) and the mixture was heated at reflux for 2 h. The reaction mixture was cooled to room temperature, diluted with toluene and filtered through celite. The filtrate was diluted with water and extracted with toluene, and the organic phases were combined and evaporated under vacuum. The residue is filtered through silica gel and recrystallized to give the target product TM1 (69.2 g, 85% yield).
  • 23
  • [ 716-53-0 ]
  • [ 62-53-3 ]
  • [ 15424-38-1 ]
YieldReaction ConditionsOperation in experiment
85% With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate; In toluene; for 2h;Reflux; Tri-tert-butylphosphine (3 mL of a 1.0 M solution in toluene, 7.32 mmol), palladium acetate (0.4 g, 1.83 mmol) and sodium tert- butoxide (22.8 g, 238 mmol) were added to 9- chloroanthracene ) And aniline (17.0 g, 183 mmol) in degassed toluene (500 mL) and the mixture heated at reflux for 2 h. The reaction mixture was cooled to room temperature, diluted with toluene and passed through diatomsSoil filtration. The filtrate was diluted with water and extracted with toluene, and the organic phases were combined and carried under vacuum evaporation. This residue was filtered through silica gel and recrystallized to give Intermediate A-1 (41.8 g, yield 85%).
  • 24
  • [ 15424-38-1 ]
  • C26H16BrN3 [ No CAS ]
  • C46H30N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; for 24h;Reflux; Sub 1 (16.9 g, 100 mmol) andSub 2 (156 g, 50 mmol) was dissolved in toluene(Dba) 3 (3 g, 7 mmol), P (t-Bu) 3 (0.7 g, 3.5 mmol)NaOt-Bu (14.8 g, 150 mmol) was added and the mixture was refluxed for 24 hours. After the reaction was completed, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO 4 and concentrated. The resulting organic material was purified by silica gel column and recrystallized.
  • 25
  • [ 2038-91-7 ]
  • [ 15424-38-1 ]
  • C33H23N [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; XPhos; In toluene; at 100 - 110℃; for 2h;Inert atmosphere; 70(2) To the machine equipped with mechanical stirring, thermometer, After replacing the three-port reaction flask in the condenser with nitrogen, Add intermediate 24c (80mmol) in sequence, Intermediate 3 (85mmol), 300ml toluene, heated to reflux for 0.5h, Cool down to 70 - 80 C, Slowly add sodium tert-butoxide (120mmol), Pd2 (dba) 3 (0.2mmol), xphos (0.4mmol), After the system is stable, it is heated to 100 - 110 C for 2h. Reduce the temperature to 25 - 30 C, add 200ml of water, stir and separate with 100ml of toluene, and extract the aqueous phase once with 200ml of toluene. Separate the liquid, combine the organic phase, add 7g of anhydrous sodium sulfate to the organic phase, stir and dry, filter The organic phase was concentrated (-0.08 0.09MPa, 55 - 60C) until it could not come out. Filtration to obtain 70mmol intermediate 24d, yield 88%
  • 26
  • [ 15424-38-1 ]
  • C46H30BrNO [ No CAS ]
  • 27
  • [ 15424-38-1 ]
  • C46H28BrN [ No CAS ]
  • C46H28BrN [ No CAS ]
  • 28
  • [ 15424-38-1 ]
  • C46H26BrN [ No CAS ]
  • 29
  • [ 15424-38-1 ]
  • C66H40N2 [ No CAS ]
  • 30
  • [ 15424-38-1 ]
  • C46H26BrN [ No CAS ]
  • C66H40N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; XPhos; In toluene; at 100 - 110℃; for 2h;Inert atmosphere; (6) To be equipped with mechanical stirring, thermometer, After replacing the three-port reaction flask in the condenser with nitrogen, Add intermediate 24h (10mmol) in sequence, Intermediate 24c (11mmol), 100ml toluene, Heating to reflux for 0.5h, Cool down to 70-80 C , Slowly add sodium tert-butoxide (15mmol), Pd2 (dba) 3 (0.05mmol), x-phos (0.1mmol), after the system is stabilized, heated to 100 ~ 110 C for 2h. Reduce the temperature to 25-30 C, add 50ml water, 50ml toluene and stir to separate. The aqueous phase is extracted once with 100ml toluene, separate the liquid, combine the organic phase, add 5g anhydrous sodium sulfate and stir to dry After filtration, the organic phase was concentrated (-0.08 to 0.09 MPa, 55 to 60 C) until it did not come out. 20 ml of petroleum ether was added with stirring and filtered to obtain 7.3 g of compound 24 in 85% yield.
  • 31
  • [ 90-93-7 ]
  • [ 15424-38-1 ]
  • C62H69N5(2+)*2Cl(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
77.2% A mixture of 4,4′-bis(diethylamino)-benzophenone (3.0g, 9.3mmol), toluene (30mL), and phosphorus (V) oxychloride (4.2mL, 15.2mmol) was vigorously stirred at 25C for 1h. Subsequently, n-phenyl-9-anthramine (1.0g, 3.7mmol) was added to the mixture. The resulting solution was stirred for 24h at 105C and then cooled to room temperature. The settled mixture was extracted using CH2Cl2 and NaCl brine. The collected organic layers were dried over anhydrous MgSO4 and evaporated. The crude dye mixture was refluxed in an acetone/ethyl acetate (1:3, v/v) binary solvent at 80C for 3h. The final solid product was filtered out and dried at 80C under vacuum for 1 day. Yield: 2.73g, 77.2%; 1H NMR (DMSO-d6, ppm): δ=10.1 (1H, s), 8.22 (2H, d), 7.31 (26H, m), 3.60 (16H, d), 1.20 (24H, t); 13C NMR (DMSO-d6, ppm): δ=12.70, 44.81, 45.46, 112.65, 113.94, 114.54, 114.63, 124.83, 125.58, 126.08, 126.33, 126.77, 127.50, 127.75, 129.55, 130.21, 130.46, 130.96, 131.19, 131.84, 132.71, 133.57, 137.00, 138.97, 139.94, 146.9, 153.82, 154.77, 155.33, 168.85, 169.83, 175.85; MALDI-TOF: m/z 882.57 (100%, [M + H]+); Elemental analysis: Calcd. for C62H69N5Cl2: C,77.96; H, 7.28; N, 7.33%. Found: C, 77.77; H, 7.42; N, 7.52.
  • 32
  • [ 90-93-7 ]
  • [ 15424-38-1 ]
  • C62H69N5O12S4(2+)*2Cl(1-) [ No CAS ]
 

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