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[ CAS No. 915088-14-1 ] {[proInfo.proName]}

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Chemical Structure| 915088-14-1
Chemical Structure| 915088-14-1
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Product Details of [ 915088-14-1 ]

CAS No. :915088-14-1 MDL No. :
Formula : C24H26BNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :QCXZGMTXGKIZBZ-UHFFFAOYSA-N
M.W : 371.28 Pubchem ID :59207617
Synonyms :

Safety of [ 915088-14-1 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 915088-14-1 ]

* 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 [ 915088-14-1 ]

[ 915088-14-1 ] Synthesis Path-Downstream   1~27

  • 1
  • [ 58530-53-3 ]
  • [ 915088-14-1 ]
  • [ 1361051-58-2 ]
  • 2
  • [ 915088-14-1 ]
  • [ 1361051-56-0 ]
  • 3
  • [ 915088-14-1 ]
  • [ 1361051-57-1 ]
  • 4
  • [ 16292-17-4 ]
  • [ 915088-14-1 ]
  • [ 1361051-55-9 ]
  • 5
  • [ 61676-62-8 ]
  • [ 78600-33-6 ]
  • [ 915088-14-1 ]
YieldReaction ConditionsOperation in experiment
58% issolve <strong>[78600-33-6]3-bromo-N,N-diphenylaniline</strong> (1.62g, 5mmol)40 mL of freshly steamed tetrahydrofuran was placed in a low temperature reactor at -78 C for 10 min.After degassing three times with freezing, 3 mL of n-butyllithium (2.40 M, 7 mmol) was slowly added dropwise.After activation for 4 h, slowly add about 2 mL of isopropanol pinacol borate (7 mmol).Stir at room temperature for 48 h.The mixture was extracted with dichloromethane and concentrated to give a crude product.Purification by column chromatography (petroleum ether: methylene chloride = 1: 2) gave white solid (0.84 g,yield: 58%).
  • 6
  • [ 915088-14-1 ]
  • [ 1443793-90-5 ]
  • [ 1542164-20-4 ]
  • 7
  • [ 78600-33-6 ]
  • [ 73183-34-3 ]
  • [ 915088-14-1 ]
YieldReaction ConditionsOperation in experiment
38% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In dimethyl sulfoxide; at 80℃; for 10h;Inert atmosphere; A mixture of 10 g of 3-bromo-N, N-diphenylaniline,11.7 g of bispinacolato diboron,9.1 g of KOAc and 0.76 g of [1,1'-bis (biphenylphosphino) ferrocene] dichloropalladium (II) [Pd (dppf) Cl2]And 100 ml (ml) of DMSO were placed in a round bottom three-necked flask under a nitrogen atmosphere,And stirred at 80 C for 10 hours.The reaction solution was cooled and extracted with dichloromethane and water,And concentrating the extracted solution. The concentrated solution was subjected to column chromatography using a mixed solvent of dichloromethane and n-hexane and concentrated to give 3.9 g of N, N-diphenyl-3- (4,4,5,5-tetramethyl- 1,3,2-dioxaborane-2-yl) aniline (yield 38%).
38% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In dimethyl sulfoxide; at 80℃; for 10h;Inert atmosphere; 10 g of <strong>[78600-33-6]3-bromo-N,N-diphenylaniline</strong>, 11.7 g of bis(pinacolato)diboron, 9.1 g of potassium acetate,0.76 g of [1,1-bis(biphenylphosphino)ferrocene]dichloromethane (II),100 ml of DMSO was placed in a round bottom three-necked flask under a nitrogen atmosphere and stirred at 80C for 10 hours.The reaction solution was cooled and extracted with dichloromethane and water.The extracted solution was concentrated, and then the concentrated solution was subjected to column chromatography using a mixed solvent of dichloromethane and n-hexane and concentrated to thereby obtain 3.9 g of N,N-diphenyl-3-(4,4,5). , 5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (yield: 38%).
YieldReaction ConditionsOperation in experiment
87% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In N,N-dimethyl-formamide; at 90℃; General procedure: Said M 1-I-1 obtained in the synthesis (112.78g, 347.9mmol) senses a rotation velocity of the disk to a DMF to in round bottom flask , Bis (pinacolato) diboron (97.17g, 382.6mmol), Pd (dppf) Cl 2 (8.52g, 10.4mmol), KOAc (102.42g, 1043.6mmol) added 90 C stirring section. When reaction is completed by etching are removed and then the DMF via fractional distillation CH 2 Cl 2 extracted and water. Organic layer MgSO 4 to dry a silicagel column with a compound formed after the products and recrystallization 114.95g (yield: 89%)is obtained.
86% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In N,N-dimethyl-formamide; at 90℃; General procedure: Wherein M 2-I-1 (63.01 g, 194.3 mmol) to a round bottom flask was charged with DMF (970 ml) to dissolve later, Bis (pinacolato) diboron (54.29 g, 213.8 mmol), PdCl2 (dppf) (4.76 g, 5.8 mmol), was added KOAc (57.22 g, 583 mmol) and the resulting mixture was stirred at 90 C. After completion of reaction by distillation to remove DMF and CH2Cl2. And extracted with water. The organic layer was dried over MgSO4 and concentrated and the resulting product was compound silicagel column and recrystallization 62.78 g (yield:87% was obtained).
  • 9
  • [ 915088-14-1 ]
  • C24H15BrClN [ No CAS ]
  • C42H29BrN2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With tetrakis(triphenylphosphine) palladium(0); sodium hydroxide; In tetrahydrofuran; water; at 80℃; General procedure: Said Sub 1-V-1 obtained in the synthesis (46.13g, 106.6mmol) senses a rotation velocity of the disk to a in round bottom flask THF to, M 1-1 (47.49g, 127.9mmol), Pd (PPh 3) 4 (3.7g, 3.2mmol), NaOH (12.79g, 319.8mmol), water are added 80 C stirring section. When reaction is completed CH 2 Cl 2 and a water extraction of organic layer after MgSO 4 to dry a silicagel column with a compound formed after the products and recrystallization 50.92g (yield: 80%)is obtained.Said Sub 1-V-1 obtained in the synthesis (27.86g, 64.4mmol) to M 1-12 (28.68g, 77.3mmol), Pd (PPh 3) 4 (2.23g, 1.9mmol), NaOH (7.73g, 193.1mmol), THF, 30.57g the products reusing synthetic said Sub 1-VI-1 water (yield: 74%)is obtained.
  • 10
  • [ 915088-14-1 ]
  • [ 57103-20-5 ]
  • C36H25BrN2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene;Inert atmosphere; Reflux; A mixture of 10 g of <strong>[57103-20-5]3,6-dibromo-9-phenyl-9H-carbazole</strong>,4.6 g of the intermediate 1 obtained in Preparation Example 1,0.3 g of Pd (PPh3) 4 and5.1 g of K2CO3 was placed in a round bottom three-necked flask under a nitrogen atmosphere,And 100 ml of toluene was added.The mixture was stirred and refluxed.After completion of the reaction, the resulting solution was washed with dichloromethane and water. Collecting organic layer,Dried over MgSO4 and separated by column,Thus, 4.1 g of intermediate 13 was obtained (yield 58percent).
  • 11
  • [ 915088-14-1 ]
  • [ 57103-20-5 ]
  • C54H39N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
49% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene;Inert atmosphere; Reflux; 2 g of <strong>[57103-20-5]3,6-dibromo-9-phenyl-9H-carbazole</strong>,3.9 g of the intermediate 1 synthesized in Preparation Example 1,0.3 g of Pd (PPh3) 4 and 4.1 g of K2CO3 were placed in a round bottom three-necked flask under a nitrogen atmosphere,And 50 ml of toluene was added.The mixture was stirred and refluxed.After completion of the reaction,The reaction solution was washed with dichloromethane and water.The moisture of the collected organic layer was then removed using MgSO4.The reaction mixture was separated by column and recrystallized,Thus, 1.8 g of compound 1 (yield 49percent) was obtained.
  • 12
  • [ 915088-14-1 ]
  • C66H48N4 [ No CAS ]
  • 13
  • [ 915088-14-1 ]
  • [ 16372-96-6 ]
  • C48H36N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In methanol; toluene; at 65℃; for 4h;Inert atmosphere; 1.5 g Intermediate 1 prepared in Preparation Example 13.6 g Intermediate 5 prepared in Preparation Example 50.7 g of tetrakis(triphenylphosphine)palladium(0), 2.5 g of potassium carbonate, 50 ml of toluene, and 20 ml of methanol were placed in a 250 ml round bottom three-necked flask under a nitrogen atmosphere.And stirred at 65 C for 4 hours.The reaction solution was cooled, extracted with dichloromethane and water, then column chromatography using a mixed solvent of dichloromethane and n-hexane, and concentration and recrystallization were performed, thus obtaining 2.7 g of Compound 1 (yield 90%).
  • 14
  • [ 915088-14-1 ]
  • C40H27Br [ No CAS ]
  • C58H41N [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; at 90℃; for 24h;Inert atmosphere; n a 100 mL round bottom flask, M6 (0.8 g, 5 mmol), M3 (2.93 g, 5 mmol), tetrakis(triphenylphosphine)palladium (120 mg, 0.105 mmol), potassium carbonate (5.52 g, 40 mmol) dissolved in 40 mL of toluene and A 20 mL aqueous solution was refluxed at 90 C for 24 hours under a nitrogen atmosphere. The mixture was extracted with dichloromethane, concentrated to give a crude product, which was purified by column chromatography ( petroleum ether: dichloromethane= 2: 1) gave a yellow solid (2.59 g, yield: 69%).
  • 15
  • [ 915088-14-1 ]
  • 6-bromo-2-iodothiophene[2,3-b]pyrazine [ No CAS ]
  • 3-(6-bromothiophen[2,3-b]pyrazin-2-yl)-N,N-diphenylaniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 85℃; for 12h;Inert atmosphere; 2) In a 500ml three-neck bottle,Add 6-bromo-2-iodothiophene [2,3-b]pyrazine (34.10 g, 100 mmol),3-diphenylaminophenyl boronate (37.13 g, 100 mmol),Potassium carbonate (27.64 g, 200 mmol), 150 g of toluene, 75 g of ethanol,75g water, tetrakis(triphenylphosphine)palladium was added under the protection of N2, and reacted at 85 C for 12 h.The TLC monitoring reaction was completed. After cooling to room temperature, the reaction solution was washed twice with water (200 ml).The organic phase is obtained by liquid separation, decolorized by adding activated carbon, filtered, and the solvent is distilled off under reduced pressure.Recrystallized twice with ethyl acetate,Drying under vacuum gave the intermediate 3-(6-bromothiophen[2,3-b]pyrazin-2-yl)-N,N-diphenylaniline.
  • 16
  • [ 915088-14-1 ]
  • 6-bromo-2-iodothiophene[2,3-b]pyrazine [ No CAS ]
  • C66H41N5OS [ No CAS ]
  • 17
  • [ 915088-14-1 ]
  • 9-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-9H-carbazole [ No CAS ]
  • 4,5-dibromo-9H-carbazole [ No CAS ]
  • N,N-diphenyl-3-(9'-phenyl-9H,9'H-[4,4'-biscarbazole]-5-yl)aniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
1) In a 500ml three-neck bottle,Add 4,5-dibromo-9H-carbazole (32.50 g, 100 mmol),3-diphenylaminobenzene borate (37.13 g, 100 mmol),Potassium carbonate (27.64 g, 200 mmol), 150 g of toluene, 75 g of ethanol, 75 g of water, tetrakis(triphenylphosphine)palladium was added under N2 protection, and reacted at 85 C for 12 h.The TLC monitors the completion of the reaction and begins to cool down. After falling to room temperature,9-Phenyl-9H-carbazole-4-borate (36.93 g, 100 mmol) was added to a three-necked flask and reacted at 85 C for 12 h.The reaction was completed by TLC. After cooling to room temperature,The reaction solution was washed twice with water (200 ml), and the mixture was separated to give an organic phase.Recrystallized twice with ethyl acetate,Drying under vacuum gave the intermediate N,N-diphenyl-3-(9'-phenyl-9H,9'H-[4,4'-biscarbazole]-5-yl)aniline.
  • 18
  • [ 915088-14-1 ]
  • [ 1416893-93-0 ]
  • 3-(6-(10-(3-(diphenylamino)phenyl)anthracen-9-yl)pyren-1-yl)-N,N-diphenylaniline [ No CAS ]
  • 19
  • [ 591-18-4 ]
  • [ 915088-14-1 ]
  • 20
  • [ 122-39-4 ]
  • [ 915088-14-1 ]
  • 21
  • [ 608-30-0 ]
  • [ 915088-14-1 ]
  • N3,N3,N3'',N3"-tetraphenyl-[1,1': 3',1"-terphenyl]-2,3,3''-triamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
17.5 g With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tetrabutylammomium bromide; palladium diacetate; potassium carbonate; In water; toluene; for 2h;Inert atmosphere; Reflux; 2,6-Dibromoaniline (8.5 g), N, N-diphenyl-3- (4,4,5,5) -Tetramethyl-1,3,2-dioxaborolan-2-yl) aniline (27.7 g), Potassium carbonate (18.7 g), Tetrabutylammonium bromide (3.3 g), Palladium acetate (II) (0.15 g), Dicyclohexyl (2', 6'-dimethoxy- [1, 1'-biphenyl] -2-yl) phosphine (0.56 g), toluene (85 ml), A flask containing Solmix A-11 (manufactured by Japan Alcohol Trading Co., Ltd., solmix, 40 ml) and water (20 ml) was placed in a nitrogen atmosphere. The mixture was heated under reflux for 2 hours. After the reaction is complete The mixture was cooled to room temperature, the solvent of the organic layer was distilled off under reduced pressure, and the obtained solid was dissolved in toluene. It was passed through a Kagelpas column (eluent: toluene, heptane). Fraction containing the object After distilling off the solvent under reduced pressure, it was recrystallized from toluene and heptane to form a white solid. do it N3, N3, N3 ", N3" -tetraphenyl- [1,1': 3', 1 "-terphenyl] -2'3,3" -triamine (17.5 g) was obtained.
  • 22
  • [ 1722-12-9 ]
  • [ 915088-14-1 ]
  • [ 2640665-53-6 ]
YieldReaction ConditionsOperation in experiment
65 % With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene at 100℃; Inert atmosphere; Schlenk technique;
  • 23
  • [ 22536-63-6 ]
  • [ 915088-14-1 ]
  • [ 2945121-95-7 ]
YieldReaction ConditionsOperation in experiment
76 % With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene at 100℃; Inert atmosphere; Schlenk technique;
  • 24
  • [ 915088-14-1 ]
  • [ 33034-67-2 ]
  • [ 2945121-96-8 ]
YieldReaction ConditionsOperation in experiment
80 % With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene at 100℃; Inert atmosphere; Schlenk technique;
  • 25
  • [ 14508-49-7 ]
  • [ 915088-14-1 ]
  • [ 2945121-98-0 ]
YieldReaction ConditionsOperation in experiment
88 % With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene at 100℃; Inert atmosphere; Schlenk technique;
  • 26
  • [ 5190-68-1 ]
  • [ 915088-14-1 ]
  • [ 2945122-00-7 ]
YieldReaction ConditionsOperation in experiment
55 % With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene at 100℃; Inert atmosphere; Schlenk technique;
  • 27
  • [ 915088-14-1 ]
  • [ 259092-66-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
25.3 % With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene Inert atmosphere; Reflux; 3 Under an argon atmosphere, intermediates 8 (9.8 g, 1.0 equivalents, 26.30 mmol), intermediate 9 (6.73 g, 1.0 equivalents, 26.30 mmol), tetrakis (triphenylphosphine) palladium (0) (1.5 g, 0.05 equivalents, 1.31 mmol), Na 2 CO3(6. 9 g, 2.0 equivalents, 65.74 mmol), toluene (98 ml), ethanol (24 ml) and H2O (78 ml) were added to thethree-prong flask and stirred under heat and stirring under reflux for 12 hours. After cooling to room temperature, the reaction solution was filtered to obtain crystals. THF was added to dissolve the crystals, then passed through a silica gel pad, and the solvent was removed by reduced pressure distillation to obtain intermediate 10 (2.8 g, yield: 25.3%).
25.3 % With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene Inert atmosphere; Reflux; 3 Synthesis of Intermediate 10 In an argon atmosphere, Intermediate 8 (9.8 g, 1.0 eq, 26.30 mmol), Intermediate 9 (6.73 g, 1.0 eq, 26.30 mmol), tetrakis(triphenylphosphine)palladium(0) (1.5 g, 0.05 eq, 1.31 mmol), Na2CO3 (6.9 g, 2.0 eq, 65.74 mmol), toluene (98 ml), ethanol (24 m1), and H2O (78 ml) were added to a three-neck flask, and heated while stirring under reflux for 12 hours. After cooling to room temperature, the reaction solution was filtered to obtain crystals. After dissolving the crystals by adding THF thereto, the reaction solution was passed through a pad of silica gel, and the solvent was removed therefrom by distillation under reduced pressure to obtain Intermediate 10 (2.8 g, yield: 25.3%).
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