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[ CAS No. 136630-39-2 ]

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CAS No. :136630-39-2 MDL No. :MFCD09033507
Formula : C12H7Br2N Boiling Point : 459°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :325.00 g/mol Pubchem ID :11151503
Synonyms :

Safety of [ 136630-39-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 136630-39-2 ]

  • Upstream synthesis route of [ 136630-39-2 ]
  • Downstream synthetic route of [ 136630-39-2 ]

[ 136630-39-2 ] Synthesis Path-Upstream   1~20

  • 1
  • [ 439797-69-0 ]
  • [ 136630-39-2 ]
YieldReaction ConditionsOperation in experiment
80% With triphenylphosphine In 1,2-dichloro-benzene 2.5 g (8 mmol) 4,4’-dibromo biphenyl was used(utilized) to perform a cyclization reaction to synthesize 2.08g (80percent) of 4,4’-dibromo carbazole. The 4,4’-dibromo carbazole and iodinated phenyl were dissolved in 40 ml of toluene to synthesize Intermediate C through a buchwald reaction.
73.8% With triphenylphosphine In N,N-dimethyl acetamideInert atmosphere; Reflux Dibromo-2-nitrobiphenyl (17.85 g, 50 mmol) and triphenylphosphine (32.75 g, 125 mmol) were dissolved in 300 mL of N, N-dimethylacetamide under an argon atmosphere The reaction was refluxed overnight. The reaction was stopped and cooled to room temperature. The mixture was extracted with methylene chloride and washed with water four to five times. After drying, the residue was purified by silica gel column chromatography (petroleum ether / methylene chloride = 2: 1) using 200 to 300 mesh, and recrystallized from ethanol to give white Solid (12 g, 73.8percent).
70% With triphenylphosphine In 1,2-dichloro-benzeneInert atmosphere; Reflux 4,4’-Dibromo-2-nitro-biphenyl (2.04 g, 5.42 mmol) and PPh3 (3.80g, 14.3 mmol) were refluxing in 1,2-dichlorobenzen (14 mL) under Ar over night. Then the solvent is removed byevaporation under vacuum. The residue was purified with silica chromatography (eluent:dichloromethane/hexanes = 0percent to 44percent). A brown solid (1.29 g, 70percent) was obtained asintermediate 1.
65% at 160℃; 2,7-dibromo-9-H-carbazole (8): In a 100 mL flame-dried flask, 4,4'-Dibromo-2-nitrobiphenyl (10 g, 28 mmol) was solubilized in 35 mL of triethyl phosphite (P(OEt)3). The reaction was mixed overnight at 160 °C. The reaction mixture was then allowed to cool down at room temperature and P(OEt)3 was distilled off under vacuum, followed by a flash chromatography in cyclohexane to obtain the final product as white crystals (Yield: 65percent). 1H NMR (400 MHz, CD2Cl2): δ (ppm) 8.02 (d, J = 8.3 Hz, 2H); 7.72 (s, 2H); 7.33 (d, J = 8.3 Hz, 2H). 13C NMR (101 MHz, CD2Cl2): δ (ppm) 141.96, 123.26, 122.55, 122.45, 119.94, 114.84.
62% for 18 h; Inert atmosphere; Reflux Into the 4,4'-dibromo-2-nitrobiphenyl (compound f-1) to 16.5g 2-neck RBF takes a vacuum. After all caught the Vacuum fill with nitrogen gas. After that, insert the triethyl phosphite (triethyl phospite) 60mL was refluxed for 18 hours. After the reaction was terminated with vacuum distillation to remove the solvent as much as possible The residue was purified by column chromatography: to give the (nucleic acid eluent) to give the 2,7-dibromo-9H-carbazole (compound f-2). (Yield: 62percent)
51% With triphenylphosphine In chlorobenzene at 120℃; for 16 h; A solution of (7) (4.0 g, 11.21 mmol) and triphenylphosphine(7.20 g, 27.45 mmol) in 45 mL of chlorobenzene was stirred at120 C for 16 h. The solution was extracted with ethyl acetate andwater, and the organic phasewas dried with anhydrous MgSO4. Thecrude product was concentrated in vacuo and purified by gelchromatography (silica gel, DCM/hexane 1/2 in volume ratio asthe eluant) to give a white solid (1.86 g, 51percent). 1H NMR (CDCl3, ppm):7.35e7.36 (d, J 8.0 Hz, 2H, aromatic protons), 7.58 (s, 2H, aromaticprotons), 7.86e7.88 (d, J 8.0 Hz, 2H, aromatic protons), 8.10 (s, 1H,eNH). 13C NMR (CDCl3, ppm): 113.83, 119.73, 121.45, 121.79, 132.29,140.29. MASS (EI): m/z 325.
51.2% With triphenylphosphine In 1,2-dichloro-benzene for 18 h; Reflux; Inert atmosphere Under nitrogen protection,In 250mlA solution of A3 (10 g, 28.0 mmol), triphenylphosphine (18. 4 g, 70 mmol) and 110 ml of o-dichlorobenzene were added successively under reflux to reflux and reacted for 18 hours with stirring. After completion of the reaction, the reaction solution was allowed to cool to room temperature and then poured into an appropriate amount of water and extracted with methylene chloride. The resulting organic phase was dried over anhydrous magnesium sulfate and the organic solvent was removed by rotary evaporator. The initial product was purified by chromatography And the eluent was petroleum ether / ethyl acetate to give 4.7 g of a pale yellow solid (yield: 51.2percent).
48% at 150℃; for 24 h; Inert atmosphere 7.8 g of Compound 1 was dissolved in 30 mL of triethylphosphite and stirred well. The above will be under the protection of nitrogen The system was heated to 150 ° C for 24 hours. After vacuum distillation to remove excess solvent, the residue was purified by column chromatography. most A white solid was obtained as a pure product in 48percent yield.

Reference: [1] Macromolecules, 2018, vol. 51, # 18, p. 7407 - 7416
[2] Journal of Materials Chemistry, 2011, vol. 21, # 13, p. 4918 - 4926
[3] Patent: KR2015/144421, 2015, A, . Location in patent: Paragraph 0312; 0313; 0315
[4] Journal of Organic Chemistry, 2005, vol. 70, # 13, p. 5014 - 5019
[5] Journal of Organic Chemistry, 2017, vol. 82, # 19, p. 9931 - 9936
[6] Patent: CN105001233, 2017, B, . Location in patent: Paragraph 0100; 0102; 0104
[7] Journal of Polymer Science, Part A: Polymer Chemistry, 2010, vol. 48, # 23, p. 5479 - 5489
[8] Patent: WO2014/93225, 2014, A2, . Location in patent: Page/Page column 185
[9] Polymer, 2017, vol. 119, p. 274 - 284
[10] Patent: KR101495152, 2015, B1, . Location in patent: Paragraph 0164; 0168-0169
[11] Macromolecules, 2013, vol. 46, # 10, p. 3850 - 3860
[12] Synthesis, 2003, # 16, p. 2470 - 2472
[13] CrystEngComm, 2017, vol. 19, # 19, p. 2632 - 2643
[14] Polymer, 2014, vol. 55, # 23, p. 6058 - 6068
[15] Patent: CN103951705, 2016, B, . Location in patent: Paragraph 0054-0056
[16] Chemical Communications, 2016, vol. 52, # 57, p. 8838 - 8841
[17] Organic and Biomolecular Chemistry, 2011, vol. 9, # 10, p. 3615 - 3618
[18] Patent: CN106632264, 2017, A, . Location in patent: Paragraph 0028; 0029; 0030
[19] Heterocycles, 2010, vol. 81, # 4, p. 977 - 984
[20] Chemistry Letters, 2008, vol. 37, # 3, p. 344 - 345
[21] Tetrahedron, 2010, vol. 66, # 51, p. 9641 - 9649
[22] Polymer, 2010, vol. 51, # 14, p. 3196 - 3202
[23] Tetrahedron, 2011, vol. 67, # 43, p. 8248 - 8254
[24] Bulletin of the Korean Chemical Society, 2011, vol. 32, # 7, p. 2461 - 2464
[25] Journal of Polymer Science, Part A: Polymer Chemistry, 2011, vol. 49, # 20, p. 4458 - 4467
[26] Chemistry - A European Journal, 2012, vol. 18, # 47, p. 15065 - 15072
[27] Science China Chemistry, 2013, vol. 56, # 8, p. 1119 - 1128
[28] Journal of Polymer Science, Part A: Polymer Chemistry, 2016, vol. 54, # 17, p. 2774 - 2784
[29] Zeitschrift fur Anorganische und Allgemeine Chemie, 2017, vol. 643, # 15, p. 999 - 1003
[30] Journal of Materials Chemistry A, 2017, vol. 5, # 38, p. 20263 - 20276
[31] Journal of Materials Chemistry B, 2017, vol. 5, # 24, p. 4725 - 4731
[32] New Journal of Chemistry, 2018, vol. 42, # 4, p. 2830 - 2837
  • 2
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YieldReaction ConditionsOperation in experiment
80% With N-Bromosuccinimide In tetrahydrofuran for 4 h; Cooling with ice; Darkness; Inert atmosphere In a 100 mL jar, 1.00 g (5.99 mmol) of carbazole was added, dissolved in tetrahydrofuran, and the jar was placed in an ice bath and protected from light.Then, 2.67 g (15 mmol) of NBS was dissolved in tetrahydrofuran and poured into a constant pressure dropping funnel. The solution was slowly dropped into a 100 mL single-mouth flask, and the mixture was stirred in an ice bath under nitrogen for 4 h.The reaction was poured into 100 mL of water and extracted three times with ethyl acetate.The resulting liquid was spin-dried and subjected to column chromatography with ethyl acetate: petroleum ether = 1:200 to give 1.56 g (4.8 mmol) of white.Solid, compound 2, 80percent yield.
Reference: [1] Patent: CN107915753, 2018, A, . Location in patent: Paragraph 0029; 0030; 0031
[2] Bulletin of the Korean Chemical Society, 2011, vol. 32, # 7, p. 2461 - 2464
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YieldReaction ConditionsOperation in experiment
70% at 160℃; for 5 h; Inert atmosphere General procedure: The 4,4'-dihalo-2-nitrobiphenyl (0.004 mol) and 4-nitrotoluene (0.006 mol) were heated at 160 °C with an excess of trialkyl phosphite (0.05 mol) under argon for 5 h (a-h, j, k) or 17 h (i, m). After cooling the excess of trialkyl phosphite and the trialkyl phosphate were removed under vacuum. The reaction mixture was chromatographed (column 3.x.60 cm) on silica gel in toluene/heptane (1:1 by vol). The main product 7 (Rf=0.8-0.9) was easy separated from the side product 8 (Rf=0.5-0.6). The prepared new materials (7a-m) were characterized by TLC, elemental analysis, melting point, 1H and 13C NMR and FTIR. The chromatographic pure materials 7 were for melting point determination recrystallized from methanol. The non-alkylated carbazoles 8 were identified by means of separately prepared 2,7-diiodocarbazole10 (8a-c), 2,7-dibromocarbazole8 (8d-f), 2,7-dichlorocarbazole7 (8g-i), and with commercial carbazole11 (8j-m).
Reference: [1] Tetrahedron, 2012, vol. 68, # 25, p. 5075 - 5080
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Reference: [1] European Journal of Medicinal Chemistry, 1997, vol. 32, # 10, p. 781 - 793
[2] Molecular Crystals and Liquid Crystals, 2006, vol. 459, # 1, p. 85/[365]-94/[374]
[3] Journal of Organic Chemistry, 1991, vol. 56, # 21, p. 6248 - 6250
  • 5
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Reference: [1] Patent: US2005/225235, 2005, A1,
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Reference: [1] Journal of Organic Chemistry, 2003, vol. 68, # 13, p. 5091 - 5103
  • 7
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Reference: [1] Journal of Organic Chemistry, 2005, vol. 70, # 13, p. 5014 - 5019
[2] Synthesis, 2003, # 16, p. 2470 - 2472
[3] Organic and Biomolecular Chemistry, 2011, vol. 9, # 10, p. 3615 - 3618
[4] Journal of Polymer Science, Part A: Polymer Chemistry, 2010, vol. 48, # 23, p. 5479 - 5489
[5] Journal of Materials Chemistry, 2011, vol. 21, # 13, p. 4918 - 4926
[6] Polymer, 2010, vol. 51, # 14, p. 3196 - 3202
[7] Tetrahedron, 2011, vol. 67, # 43, p. 8248 - 8254
[8] Bulletin of the Korean Chemical Society, 2011, vol. 32, # 7, p. 2461 - 2464
[9] Journal of Polymer Science, Part A: Polymer Chemistry, 2011, vol. 49, # 20, p. 4458 - 4467
[10] Chemistry - A European Journal, 2012, vol. 18, # 47, p. 15065 - 15072
[11] Science China Chemistry, 2013, vol. 56, # 8, p. 1119 - 1128
[12] Macromolecules, 2013, vol. 46, # 10, p. 3850 - 3860
[13] Polymer, 2014, vol. 55, # 23, p. 6058 - 6068
[14] Journal of Polymer Science, Part A: Polymer Chemistry, 2016, vol. 54, # 17, p. 2774 - 2784
[15] Patent: KR101495152, 2015, B1,
[16] Chemical Communications, 2016, vol. 52, # 57, p. 8838 - 8841
[17] Patent: KR2015/144421, 2015, A,
[18] Patent: CN103951705, 2016, B,
[19] Zeitschrift fur Anorganische und Allgemeine Chemie, 2017, vol. 643, # 15, p. 999 - 1003
[20] Journal of Materials Chemistry A, 2017, vol. 5, # 38, p. 20263 - 20276
[21] Patent: CN106632264, 2017, A,
[22] Polymer, 2017, vol. 119, p. 274 - 284
[23] Journal of Materials Chemistry B, 2017, vol. 5, # 24, p. 4725 - 4731
[24] Patent: CN105001233, 2017, B,
[25] CrystEngComm, 2017, vol. 19, # 19, p. 2632 - 2643
[26] New Journal of Chemistry, 2018, vol. 42, # 4, p. 2830 - 2837
[27] Macromolecules, 2018, vol. 51, # 18, p. 7407 - 7416
  • 8
  • [ 568592-11-0 ]
  • [ 136630-39-2 ]
Reference: [1] Journal of Organic Chemistry, 2003, vol. 68, # 13, p. 5091 - 5103
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Reference: [1] Journal of Organic Chemistry, 2003, vol. 68, # 13, p. 5091 - 5103
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Reference: [1] Journal of Organic Chemistry, 2003, vol. 68, # 13, p. 5091 - 5103
  • 11
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Reference: [1] Journal of Organic Chemistry, 2003, vol. 68, # 13, p. 5091 - 5103
  • 12
  • [ 91371-12-9 ]
  • [ 136630-39-2 ]
Reference: [1] Molecular Crystals and Liquid Crystals, 2006, vol. 459, # 1, p. 85/[365]-94/[374]
[2] European Journal of Medicinal Chemistry, 1997, vol. 32, # 10, p. 781 - 793
[3] Journal of Organic Chemistry, 1991, vol. 56, # 21, p. 6248 - 6250
  • 13
  • [ 136630-39-2 ]
  • [ 406726-92-9 ]
Reference: [1] Journal of Organic Chemistry, 2004, vol. 69, # 17, p. 5705 - 5711
[2] Patent: CN107266354, 2017, A,
[3] Patent: CN107445885, 2017, A,
  • 14
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  • [ 958261-51-3 ]
Reference: [1] Patent: KR101495152, 2015, B1,
  • 15
  • [ 111-25-1 ]
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  • [ 654676-12-7 ]
YieldReaction ConditionsOperation in experiment
99% With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In water; toluene at 80℃; for 14 h; General procedure: A mixture of the corresponding 2,7-disubstituted 9H-carbazole (for the synthesis see Supplementary data) (10mmol), alkylbromide (10.5mmol), BnEt3NCl (0.227g, 1mmol), toluene (20mL) and NaOH solution (0.42g, 10.5mol, in water 50percentw/v) was stirred at 80°C for 14h. Then the reaction mixture was cooled to rt., poured into 50mL of water and acidified with 10percent hydrochloric acid to pH∼2. Organic layer was separated and water phase additionally was extracted with toluene (2×10mL). Combined extracts were washed with water (2×25mL), dried over Na2SO4, filtered and evaporated to dryness. The obtained crude products of the alkylation reaction were purified by column chromatography to give N-alkylcarbazoles 1a–f.
99.8% With sodium hydride In dimethyl sulfoxide at 20 - 30℃; Inert atmosphere Under the protection of argon, in 100 ml of the three-port are sequentially added in the bottle 2,7-dibromo diphenylenimine 4.88g (15mmol), hydrogenated sodium 0.72g, DMSO solvent 30 ml, controlling the reaction temperature 20-30°C, dropwise 1-bromo-hexane, HPLC detection reaction is ended. 100 ml water quenching, with 100 ml dichloromethane extraction, layered, for water 50 ml dichloromethane extraction, combined with the phase, drying by anhydrous magnesium sulphate, pressure reducing and recovering the solvent, the crude solid obtained, using dichloromethane-methanol of performing recrystallization, get white product 2,7-di-bromo-N-hexyl carbazole 5.87g, purity 99.8percent (HPLC), the yield of 95.6percent, melting point 70.6-72.5 °C. 1 HNMR (400MHz, CDCl 3), δ: 0.858-0.906 (3H, t), 1.295-1.351 (6H, m), 1.786-1.885 (2H, m), 4.168-4.217 (2H, t), 7.320-7.354 (2H, dd), 7.525-7.530 (2H, d), 7.875-7.903 (2H, d).
Reference: [1] Dyes and Pigments, 2016, vol. 124, p. 133 - 144
[2] Patent: CN105384679, 2016, A, . Location in patent: Paragraph 0009; 0025; 0026; 0027
[3] Journal of Materials Chemistry C, 2016, vol. 4, # 26, p. 6270 - 6279
[4] Heterocycles, 2010, vol. 81, # 4, p. 977 - 984
[5] Journal of Organic Chemistry, 2008, vol. 73, # 23, p. 9207 - 9213
[6] Tetrahedron, 2011, vol. 67, # 43, p. 8248 - 8254
[7] Chemistry - A European Journal, 2012, vol. 18, # 47, p. 15065 - 15072
[8] Journal of Polymer Science, Part A: Polymer Chemistry, 2016, vol. 54, # 17, p. 2774 - 2784
  • 16
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  • [ 871696-12-7 ]
Reference: [1] Tetrahedron, 2011, vol. 67, # 43, p. 8248 - 8254
  • 17
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  • [ 955964-73-5 ]
YieldReaction ConditionsOperation in experiment
90%
Stage #1: With potassium hydroxide In dimethyl sulfoxide at 80℃; for 1 h;
Stage #2: Heating
9-Heptadecanyl-2,7-dibromocarbazole (9): 2,7-dibromo-9-H-carbazole (4 g, 12 mmol) and potassium hydroxide (0.84 g, 17.8 mmol) were solubilized in dry DMSO (40 mL). The reaction mixture was heated at 80 °C for 1 h before adding dropwise a solution of 9-Heptadecane p-toluenesulfonate (6.4 g, 15.6 mmol) in 60 mL of dry DMSO. After cooling down at room temperature, the reaction mixture was poured into 300 mL of water and extracted three times with 100 mL of diethylether, dried over magnesium sulfate and the solvent was removed under vacuum. The white powder was purified by flash chromatography in cyclohexane to afford white crystals (yield: 90percent). 1H NMR (400 MHz, CDCl3): δ (ppm) 7.5 (s, 2H); 7.27 (s, 2H); 7.12 (m, 2H), 4.48 (tt, J = 10.1, 5.1 Hz, 1H); 2.20 (m, 2H); 1.83 (m, 2H) 1.32-1.02 (m, 28H); 0.83 (t, J = 7.0 Hz, 6H). 13C NMR (100 MHz, CDCl3): δ (ppm) 125.61; 125.23; 120.43; 118.54; 111.70, 108.87, 56.43; 33.85; 31.89; 29.53; 29.43; 29.30; 26.94; 22.73; 14.20. HRMS (EI+, m/z) [M]+ calculated (percent) for C29H41Br2N: 561.16057, found 561.16261.
78% With potassium hydroxide In dimethyl sulfoxide for 24 h; After loading the compound f-2 (1g) To a round flask, place the compound 4-f (1.9g, 1.5eq). And after inserting the KOH (1g, 5eq) above, it is injected DMSO as a solvent. And then stirred for 24 hours, the organic layer was extracted with MC and the salt water to remove the remaining water over anhydrous magnesium sulfate and, after evaporation of the solvent was recrystallized from a MC and MeOH as a white solid 2,7-dibromo-9- (heptadecane and the -9-yl) -9H-carbazole (compound f-5) obtained. (Yield: 78percent)
Reference: [1] Polymer, 2017, vol. 119, p. 274 - 284
[2] Macromolecules, 2010, vol. 43, # 22, p. 9376 - 9383
[3] Patent: KR101495152, 2015, B1, . Location in patent: Paragraph 0164; 0177-0178
[4] Journal of the American Chemical Society, 2012, vol. 134, # 46, p. 19035 - 19042
[5] Journal of Polymer Science, Part A: Polymer Chemistry, 2015, vol. 53, # 17, p. 2059 - 2068
[6] Macromolecules, 2012, vol. 45, # 21, p. 8658 - 8664
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YieldReaction ConditionsOperation in experiment
80% With palladium diacetate; tris-(o-tolyl)phosphine; sodium t-butanolate In toluene 2.5 g (8 mmol) 4,4’-dibromo biphenyl was used(utilized) to perform a cyclization reaction to synthesize 2.08g (80percent) of 4,4’-dibromo carbazole. The 4,4’-dibromo carbazole and iodinated phenyl were dissolved in 40 ml of toluene to synthesize Intermediate C through a buchwald reaction.
78% With copper; potassium carbonate In N,N-dimethyl-formamide at 130℃; Inert atmosphere Synthesis of 2,7-dibromo-9-phenyl-9H-carbazole
A mixture of 32.5 g (100 mmole) 2,7-dibromo-9H-carbazole, 20.4 g (100 mmole) iodobenzene, 9.5 g (150 mmole) of copper powder, 27.6 g (200 mmole) of potassium carbonate, and 600 ml dimethylformamide were heated at 130° C. under nitrogen overnight, then cooled to room temperature, the solution was filtered.
The filtrate was extracted three times with dichloromethane and water, dried with anhydrous magnesium sulfate, the solvent was evaporated in vacuum.
The residue was purified by column chromatography on silica(hexane-dichloromethane) afforded a white solid (31.3 g, 78 mmol, 78percent).
70% With copper; potassium carbonate In 1,2-dichloro-benzene at 140℃; for 12 h; 2,7-dibromo-9H-carbazole (3.0 g, 9.32 mmol), iodobenzene (2.1 g, 10.25 mmol), copper powder (1.8 g,27.95 mmol) and potassium carbonate (4.1 g, 29.81 mmol) were added to stirred 60 mL o-dichlorobenzene, the system at 140 °C Reflow for 12 hours. At the end of the reaction, 20 mL of distilled water was added thereto, followed by extraction with ethyl acetate, and the organic phases were combined. After drying over anhydrous magnesium sulfate, it was concentrated and column chromatography afforded 2,7-dibromo-9-phenyl-carbazole (2.4 g, 70percent yield).
Reference: [1] Patent: KR2015/144421, 2015, A, . Location in patent: Paragraph 0312; 0313; 0315
[2] Journal of Materials Chemistry, 2011, vol. 21, # 13, p. 4918 - 4926
[3] Patent: US2016/204345, 2016, A1, . Location in patent: Paragraph 0034-035
[4] Patent: CN107827808, 2018, A, . Location in patent: Paragraph 0080; 0081; 0082; 0083; 0094; 0095; 0096; 0097
[5] Journal of Materials Chemistry, 2011, vol. 21, # 15, p. 5638 - 5644
[6] RSC Advances, 2015, vol. 5, # 64, p. 51512 - 51523
[7] Patent: US9166177, 2015, B2,
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Reference: [1] Patent: CN108203427, 2018, A, . Location in patent: Paragraph 0119; 0120
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Reference: [1] Polymer, 2011, vol. 52, # 8, p. 1748 - 1754
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