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[ CAS No. 57103-20-5 ]

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CAS No. :57103-20-5 MDL No. :MFCD08276338
Formula : C18H11Br2N Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :401.10 g/mol Pubchem ID :11025791
Synonyms :

Safety of [ 57103-20-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P305+P351+P338 UN#:N/A
Hazard Statements:H302-H319-H413 Packing Group:N/A
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  • Upstream synthesis route of [ 57103-20-5 ]
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[ 57103-20-5 ] Synthesis Path-Upstream   1~12

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Reference: [1] Helvetica Chimica Acta, 2006, vol. 89, # 6, p. 1123 - 1139
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YieldReaction ConditionsOperation in experiment
85% at 20℃; [0102] 24.3 g (100 mmol) N-phenyl-3,6-dibromocarbazole in a glacial acetic acid (500 mL) solution was added with 44.9 g (200 mmol) of N-iodine succinimide to be stirred overnight at room temperature. An aqueous sodium hydrogencarbonate solution was added to the reaction mixture until the liquid properties became neutral. The mixture was filtrated and the obtained solid was washed with water and dried to give N-phenyl-3,6-diiodinecarbazole (hereinafter, shown as PhI2Cz) with a yield of 85percent. [0103] By using the obtained PhI2Cz, a coupling reaction was performed with carbazole in the similar manner as described in the synthesis of N-ethyl-3,6-di(N-carbazolyl)carbazole to give the compound in the title, N-phenyl-3,6-di(N-carbazolyl)carbazole as a beige solid (yield: 85percent). NMR data are shown in FIG. 15 (1H NMR) and FIG. 16 (13C NMR). [0104] 1H NMR(300 MHz, CDCl3) δ 7.20-7.80(m, 21H), 8.15(d, J=7.8 Hz, 4H), 8.27(s, 2H). [0105] 13C NMR(75.5 MHz, CDCl3) δ 109.7, 111.3, 119.7, 120.3, 123.2, 123.9, 125.9, 126.3, 127.2, 128.2, 130.2, 130.4, 137.1, 140.7, 141.8. [0106] It had the melting point at 283° C and showed the sublimation point at 410° C under normal pressure. Formation of a uniform film over a substrate by a vacuum evaporation method was confirmed. Absorption maximum was at 341 nm in methanol and 344 nm for the evaporated film. It was fluorescent, showing the maximum of fluorescence at 435 nm in methanol and 409 nm for the evaporated film. The HOMO level was at -5.64 eV, and the LUMO level was at -2.33 eV. The absorption spectra for the methanol solution and evaporated film are shown in FIG. 10. The respective fluorescent spectrum and excitation spectrum are shown in FIG. 11.
Reference: [1] Patent: US2005/31899, 2005, A1, . Location in patent: Page/Page column 18
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YieldReaction ConditionsOperation in experiment
100% at 20℃; for 12 h; Inert atmosphere To a solution of 9-phenyl-9H-carbazole (2.04 g, 8.05 mmol) in CCl3(15 mL) keeping in dark place, NBS (3.29 g, 18.49 mmol) was added three times.The mixture was stirred for 12 h at room temperature. Then, water was added tothe mixture to give a white precipitate. After filtration and drying, theobtained white solid was recrystallized from petroleum. Yield: 100percent.
92% With N-Bromosuccinimide In ethyl acetate at 20℃; for 52 h; First, into a 200-mL Mayer flask were put 3.7 g (15 mmol) of 9-phenyl-9H-carbazole, 5.4 g (30 mmol) of N-bromosuccinimide (abbreviation: NBS), and75 mL of ethyl acetate. At room temperature, this solution was stirred in the air for 52 hours. Then, water was added thereto and this mixture was furtherstirred. An aqueous layer of the mixture was subjected to extraction with ethyl acetate three times. The extracted solution and an organic layer werecombined, the mixture was washed with water and saturated saline, and then magnesium sulfate was added thereto. The obtained mixture was gravityfilteredand the filtrate was concentrated, so that 5.5 g of the target white powder was obtained in a yield of 92percent.
90.3% With N-Bromosuccinimide In N,N-dimethyl-formamide at 20 - 25℃; for 24.5 h; Inert atmosphere Under nitrogen protection,N-phenylcarbazole (48.6 g, 0.2 mol) was dissolved in 500 mL DMF (N, N-dimethylformamide) in a 1 L three-necked flask,NBS (N-bromosuccinimide, 78.3 g, 0.44 mol) was slowly added to the reaction system at a temperature of 20 to 25 ° C,0.5h plus completed.The reaction system was stirred at 20-25 ° C for 24 hours.After completion of the reaction to the reaction systemAn aqueous solution of sodium sulfite (500 mL, 0.05 mol / L) was added,Quenching reaction,Filter cake,After washing with deionized water,Crystallization is carried out with toluene or absolute ethanol,To give a white solid,Namely the intermediate C01-a,The yield was 90.3percent.
90% With N-Bromosuccinimide In N,N-dimethyl-formamide at 20 - 25℃; for 24.5 h; Inert atmosphere Under nitrogen protection,N-phenylcarbazole (48.6 g, 0.2 mol) was dissolved in 500 mL of DMF (N, N-dimethylformamide) in a 1 L three-necked flask,To the reaction system was slowly added NBS (N-bromosuccinimide, 78.3 g, 0.44 mol) as a solid at a controlled temperature of 20-25 ° C,0.5h plus completed.The reaction system was incubated at 20-25 ° C for 24 hours with stirring.After completion of the reaction, an aqueous solution of sodium sulfite (500 mL, 0.05 mol / L) was added to the reaction system,The reaction mixture was quenched and the filter cake was suction filtered to obtain a cake. The residue was washed with deionized water and then crystallized from toluene or absolute ethanol to give a white solid, which was 3,6-dibromo-N-phenylcarbazole in 90percent yield.
87% With N-Bromosuccinimide In chloroform at 20℃; for 3 h; Preparation of Structural Formula 1B; The Structural Formula 1A (13.2 g, 54.3 mmol) was dissolved in chloroform (300 ml), and N-bromo succinimide (20.3 g, 114.0 mmol)) was added thereto, and agitated for 3 hours at normal temperature. Distilled water was put into the reaction solution, the termination of the reaction was carried out, and the organic material layer was extracted. The reaction solution was concentrated, and recrystallized with EtOH to obtain the Structural Formula 1B (18.9 g, yield 87 percent). MS: [M+H]+ = 402
87.8% With bromine; acetic acid In dichloromethane at 20℃; Cooling with ice 0.1640 mol of N-phenyl-9H-carbazole was charged into a 2000 ml three-necked flask, washed with 320 ml of acetic acid and 960 ml of dichlorMethane dissolved, placed in ice water bath; slowly dropping 0.3280mol liquid bromine, room temperature reaction overnight,The reaction solution was neutralized with 1.5 L of 1 mol / L aqueous sodium hydroxide solution to the remaining liquid bromine, and the organic phase was separated to obtain an organic phase,Respectively, washed three times with water, liquid to take organic phase, spin dry,Washed with 300 ml PE (60-90), suction filtered, vacuum dried at 55 ° C,To give the product 3,6-dibromo-9-phenylcarbazole 0.1440 mol, 87.8percent yield.
79.04% With N-Bromosuccinimide In N,N-dimethyl-formamide at 25℃; for 5 h; N-bromosuccinimide (15.00 g, 84 mmol, 2.05 eq) is dissolved in 30 ml of dimethylformamide and then slowly added to a flask in which 30 ml of 9-phenyl-9Hcarbazole (10 g, 41 mmol, 1.0 eq) is dissolved in 30 ml of dimethylformamide. After 5 hours of reaction, the reaction product was precipitated with 200 ml of distilled water, filtered and dried to obtain 13.03 g (yield: 79.04percent) of the target compound.
64% With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; Example 3 Synthesis of Carbozole-Based (2-Arm) Fluorescent Molecular Rotor (0310) RRN 38Preparation of 3,6-dibromo-9-phenyl-9H-carbazole (0311) 9-phenyl-9H-carbazole (0.3 g, 1.23 mmol, 1 eq.) was dissolved in DMF. N-Bromosuccinimide (0.44 g, 2.47 mmol, 2 eq.) was then added slowly and the resultant mixture was allowed to stir at room temperature overnight. The reaction mixture was then poured into brine and extracted with DCM. The organic extracts were then dried with Na2SO4 and concentrated. Crude product was then re-precipitated with methanol and THF gave white solids as 3,6-dibromo-9-phenyl-9H-carbazole (0.32 g, 64percent). (0312) 1H NMR (CDCl3, 400 MHz) δ 7.24 (s, 1H), 7.48-7.52 (m, 5H), 7.59-7.64 (m, 2H), 8.20 (d, 2H, J=2.0 Hz). 13C NMR (100 MHz, CDCl3) δ 140.1, 137.0, 130.3, 129.5, 128.3, 127.2, 124.1, 123.4, 113.2, 111.7.
56.9% With bromine In dichloromethane; acetic acid Example 11
3,6-Dibromo-9-phenylcarbazole
9-Phenylcarbazole (2.000 g, 8.220 mmol) was suspended in 15 mL glacial acetic acid in a 125 ml 3-neck round bottom flask equipped with an addition funnel and a condenser.
The reaction was under N2 blanket.
Bromine (0.880 ml, 17.262 mmol) mixed with 15 mL glacial acetic acid was added dropwise and stirred at 0° C.
Upon completion of the addition the reaction was allowed to warm to room temperature and stirred for about 5 hours.
Dichloromethane (100 mL) was added, and stirred vigorously until all the solids dissolved.
Two phases were separated in the separation funnel.
The acid layer was extracted twice with 50 mL dichloromethane.
The organic layers were combined and washed with brine until the pH=7.
The organic layers were dried over MgSO4 and filtered.
Solvent was removed under vacuum.
The crude product was then recrystallized from dichloromethane. Yield: 56.9percent. M.P.: 162.7-163.6° C.

Reference: [1] Organic Electronics: physics, materials, applications, 2014, vol. 15, # 11, p. 2667 - 2676
[2] Tetrahedron, 1998, vol. 54, # 42, p. 12707 - 12714
[3] Journal of Materials Chemistry, 2011, vol. 21, # 25, p. 9139 - 9148
[4] Patent: JP2015/63518, 2015, A, . Location in patent: Paragraph 0253; 0254
[5] Patent: CN105906612, 2016, A, . Location in patent: Paragraph 0051; 0052
[6] Patent: CN105175405, 2017, B, . Location in patent: Paragraph 0039-0041
[7] Patent: EP2343277, 2011, A2, . Location in patent: Page/Page column 32
[8] Patent: CN104650044, 2017, B, . Location in patent: Paragraph 0035; 0038
[9] Synlett, 2006, # 17, p. 2841 - 2845
[10] Macromolecules, 2005, vol. 38, # 12, p. 4970 - 4976
[11] Patent: KR101638767, 2016, B1, . Location in patent: Paragraph 0109-0112
[12] Patent: US2016/195519, 2016, A1, . Location in patent: Paragraph 0310; 0311; 0312
[13] Patent: US2006/83945, 2006, A1,
[14] Journal of Materials Chemistry, 2011, vol. 21, # 13, p. 4918 - 4926
[15] Journal of Chemical Research, 2008, # 3, p. 137 - 140
[16] Chemistry - A European Journal, 2008, vol. 14, # 15, p. 4731 - 4740
[17] Journal of Nanoscience and Nanotechnology, 2010, vol. 10, # 10, p. 6811 - 6814
[18] Journal of the Chinese Chemical Society, 2012, vol. 59, # 3, p. 331 - 337
[19] Journal of Materials Chemistry, 2012, vol. 22, # 10, p. 4527 - 4534
[20] Journal of the Chinese Chemical Society, 2013, vol. 60, # 6, p. 579 - 589
[21] Chemistry - A European Journal, 2016, vol. 22, # 22, p. 7468 - 7478
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YieldReaction ConditionsOperation in experiment
85% With copper(l) iodide; 18-crown-6 ether; potassium carbonate In DMPU (1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone) at 170℃; for 20 h; Synthesis of Intermediate E; 3.25 g (10.0 mmol) of 3, 6-dibromocarbazole, 10.2 g (50.0 mmole) iodobenzene, 190 mg (1.0 mmole) of Cul, 132 mg (0.5 mmole) of 18-C-6, 2.76 g (20.0mmole) of K2CO3 were dissolved in 50 mL of DMPU, and stirred at 170°C for 20 hours. The mixture was cooled to room temperature and 50 mL of diethylether was added thereto. Then the mixture was washed with plenty of water and ammonium hydroxide solution. A collected organic layer was dried over MgSO4 to evaporate the solvent. The residue was purified using silica gel column chromatography to obtain 3.40 g of white solid Intermediate E (Yield: 85 percent). (NMR (CDCl3, 400MHz) δ (ppm) 7.92 (m, 2H), 7.55-7.47 (m, 6H), 7.36-7.16 (m, 3H); 13C NMR (CDCl3, 100MHz) δ (ppm) 142.6, 137.6, 130.2, 129.8, 127.4, 127.0, 122.8, 122.5, 115.3, 111.3).
75% With tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine; sodium t-butanolate In toluene at 100℃; for 24 h; To a round bottom flask Sub 2-1-6 (6.5g, 20mmol), Sub 2-1-2-1 (4.1g, 20mmol),Pd2 (dba) 3 (0.9g, 1mmol), PPh3 (0.5g, 2mmol ), NaOt-Bu (5.8g, 60mmol), were addedto toluene (210mL), respectively, and refluxed under stirring for 24 hours at 100 ° C.The organic layer was dried and the ether was extracted with water over MgSO4 andconcentrated and to the resulting organic silicagel column and recrystallized from a Sub2-1-7-1 6.0g (yield: 75percent) was obtained.
3.27 g With palladium diacetate; tris-(o-tolyl)phosphine; sodium t-butanolate In toluene 2.5 g (14.9 mmol) ofcarbazole was used (utilized) to perform an NI3S bromination to synthesize 2,5-dibromocar- bazole. Then, the 2,5-dibromocarbazole and iodinated phenyl were used (utilized) to synthesize 3.72 g (9.28 mmol) of Intermediate E through a buchwald reaction.
Reference: [1] Patent: EP1921082, 2008, A1, . Location in patent: Page/Page column 35-36
[2] Journal of Nanoscience and Nanotechnology, 2011, vol. 11, # 2, p. 1373 - 1376
[3] Patent: KR2015/93995, 2015, A, . Location in patent: Paragraph 0149; 0153; 0182-0184
[4] RSC Advances, 2015, vol. 5, # 64, p. 51512 - 51523
[5] Patent: KR2015/144421, 2015, A, . Location in patent: Paragraph 0317; 0318; 0319
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YieldReaction ConditionsOperation in experiment
90.5% With copper(l) iodide; caesium carbonate In N,N-dimethyl-formamide at 110℃; for 12 h; Inert atmosphere A.3,6-dibromocarbazole (200 mg, 0.62 mmol) was dissolved in DMF solvent,Then iodobenzene (188.3 mg, 0.92 mmol) was added,DL-piperidinecarboxylic acid (11.88 mg, 0.09 mmol),Cuprous oxide (8.27 mg, 0.04 mmol),Cesium carbonate (299.75 mg, 0.92 mmol),Under nitrogen protection,The reaction system was placed at 110 ° C under reflux for 12 h,After the reaction is complete,Ethyl acetate extraction,Organic layer washed three times,Dried over anhydrous sodium sulfate,The solvent is evaporated under reduced pressure;The crude product was purified by column chromatography with ethyl acetate and petroleum ether mixed solvent (20: 1)To obtain compound 3,6-dibromo-9-phenylcarbazole (white solid, 225 mg, yield 90.5percent).
Reference: [1] Patent: CN106883182, 2017, A, . Location in patent: Page/Page column 11
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Reference: [1] Patent: EP2343277, 2011, A2,
[2] Journal of Materials Chemistry, 2011, vol. 21, # 13, p. 4918 - 4926
[3] Journal of the Chinese Chemical Society, 2012, vol. 59, # 3, p. 331 - 337
[4] Journal of Materials Chemistry, 2012, vol. 22, # 10, p. 4527 - 4534
[5] Journal of the Chinese Chemical Society, 2013, vol. 60, # 6, p. 579 - 589
[6] Organic Electronics: physics, materials, applications, 2014, vol. 15, # 11, p. 2667 - 2676
[7] Patent: KR2015/144421, 2015, A,
[8] Patent: CN104650044, 2017, B,
  • 7
  • [ 591-50-4 ]
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Reference: [1] Patent: EP2343277, 2011, A2,
[2] Journal of Materials Chemistry, 2011, vol. 21, # 13, p. 4918 - 4926
[3] Journal of Materials Chemistry, 2011, vol. 21, # 25, p. 9139 - 9148
[4] Journal of the Chinese Chemical Society, 2012, vol. 59, # 3, p. 331 - 337
[5] Journal of Materials Chemistry, 2012, vol. 22, # 10, p. 4527 - 4534
[6] Journal of the Chinese Chemical Society, 2013, vol. 60, # 6, p. 579 - 589
[7] Patent: CN104650044, 2017, B,
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Reference: [1] Organic Electronics: physics, materials, applications, 2014, vol. 15, # 11, p. 2667 - 2676
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  • [ 1150-62-5 ]
  • [ 1153-85-1 ]
  • [ 57103-20-5 ]
Reference: [1] Helvetica Chimica Acta, 2006, vol. 89, # 6, p. 1123 - 1139
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  • [ 61676-62-8 ]
  • [ 57103-20-5 ]
  • [ 618442-57-2 ]
Reference: [1] Journal of Materials Chemistry, 2011, vol. 21, # 25, p. 9139 - 9148
[2] Organic Letters, 2006, vol. 8, # 22, p. 5033 - 5036
[3] Tetrahedron Letters, 2005, vol. 46, # 5, p. 855 - 858
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YieldReaction ConditionsOperation in experiment
45% With tetrakis(triphenylphosphine) palladium(0); potassium acetate In 1,4-dioxane for 5 h; Reflux 3,6-dibromo-N-phenylcarbazole (0.075 mol) was dissolved in 300 ml of dioxane,Under the addition of bis (pinacolato) diboron (0.164 mol)Potassium acetate (0.375 mol),Tetrakis (triphenylphosphine) palladium (0.00075 mol)And heated to reflux reaction 5h,The reaction was complete and the reaction was quenched and the reaction was quenched with dichloromethane and water. The organic phase was passed through a silica gel funnel and the organic phase was dried under reduced pressure. The resulting solid was subjected to column chromatography to give compound 203-1 (yield 45percent)
Reference: [1] Patent: CN106928237, 2017, A, . Location in patent: Paragraph 0212; 0213; 0214
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  • [ 618442-57-2 ]
Reference: [1] Patent: US7271406, 2007, B2,
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