Home Cart 0 Sign in  

[ CAS No. 902518-11-0 ]

{[proInfo.proName]} ,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 902518-11-0
Chemical Structure| 902518-11-0
Structure of 902518-11-0 * Storage: {[proInfo.prStorage]}

Quality Control of [ 902518-11-0 ]

Related Doc. of [ 902518-11-0 ]

SDS
Alternatived Products of [ 902518-11-0 ]
Alternatived Products of [ 902518-11-0 ]

Product Details of [ 902518-11-0 ]

CAS No. :902518-11-0 MDL No. :MFCD23135883
Formula : C18H12BrN Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :322.20 g/mol Pubchem ID :59465012
Synonyms :

Safety of [ 902518-11-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P305+P351+P338 UN#:N/A
Hazard Statements:H302-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 902518-11-0 ]

  • Upstream synthesis route of [ 902518-11-0 ]
  • Downstream synthetic route of [ 902518-11-0 ]

[ 902518-11-0 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 86-74-8 ]
  • [ 583-53-9 ]
  • [ 902518-11-0 ]
YieldReaction ConditionsOperation in experiment
83%
Stage #1: for 0.5 h; Inert atmosphere
Stage #2: at 163℃; for 38 h;
(1) The carbazole 8.36g (0.05mol), o-dibromobenzene 17.69g (0.075mol), potassium carbonate 17.97g (0.13mol) placed in the reactor, stirred, purged with nitrogen for 30min,1.91 g of cuprous iodide and 1.46 g of L-lysine were added and heated to 163 ° C. for 38 h.No raw material was detected by TLC, and a large amount of water was added to terminate the reaction. The solid was precipitated by stirring and dried under suction filtration to give 13.37 g of 9- (2-bromophenyl) carbazole as solid, yield 83percent.
55% With copper(I) oxide; potassium phosphate; N,N`-dimethylethylenediamine In toluene at 120℃; for 72 h; 9-Carbazole (6.52 g, 39 mmol), 1,2-dibromobenzene (8 mL,66.3 mmol), copper(I) oxide (1.116 g, 7.8 mmol), N,N'-dimethylethylenediamine (1.70 mL, 15.6 mmol) and anhydrous potassium phosphate (18.21 g, 85.8 mmol) were mixed in 50 mL of anhydrous toluene and heated at 120 °C for 3 days. The crude reaction mixture was extracted with dichloromethane and water. The organic layerwas dried with anhydrous MgSO4, filtered, and evaporated. The crude product was purified by column chromatography on silica gelusing 1:30 dichloromethane/hexane. The white powder wasformed. (6.95 g, Yield 55percent) 1H NMR (300 MHz, CDCl3): δ (ppm)8.14-8.17 (d, 2H), 7.85-7.88 (d, 1H), 7.47-7.57 (m, 2H), 7.37-7.45(m, 3H), 7.27-7.32 (m, 2H), 7.05-7.08 (d, 2H).
55% With copper; potassium carbonate In dimethyl sulfoxide at 20℃; for 20.5 h; Inert atmosphere; Reflux A 500-mL, three-necked round bottom flask was charged with 9.7 g (0.058 mol) of the compound carbazole in a nitrogen atmosphere and diluted with 200 mL of dimethylsulfoxide. 15 g of 1,2-dibromobenzene, 3.7 g of copper powder and 12 g of potassium carbonate were added to the diluted solution, and the mixture was stirred at room temperature for 30 minutes. The reaction solution was heated and refluxed for 20 hours. The reaction solution was cooled to room temperature and extracted with dichloromethane and distilled water. The extract was dried and concentrated under reduced pressure to obtain 10.3 g (yield: 55percent) of Compound 11-1.
53% With copper(l) iodide; 18-crown-6 ether In 1,2-dichloro-benzene at 100 - 210℃; Inert atmosphere; Darkness Carbazole (1.6700 g, 10.0 mmol), o-dibromobenzene (2.40 mL, 20.0 mmol),Copper iodide (0.1900 g, 1.0 mmol), 18-crown-6 (0.1320 g, 0.5 mmol), 60mL o-dichlorobenzene was added to the reaction flask in turn, under nitrogen protection and dark conditions,Stir heated to 100-210°C, react for 5-100 hours, stop the reaction and slowly reduce to room temperature, Most of the solvent was distilled off under reduced pressure. The solid residue was suction filtered and washed with dichloromethane solution. The organic phase was combined. Concentration and column chromatography gave N-(2-bromophenyl)carbazole; (yield: 53percent)
39% With copper(l) iodide; 1,10-Phenanthroline; potassium hydroxide In o-xylene for 8 h; Reflux; Inert atmosphere In a one-neck flask, carbazole (3.3g, 19.9mmol), o-dibromobenzene (4.5g, 19.9mmol), CuI (0.8g, 4.0mmol), 1,10-phenanthroline monohydrate (0.8g, 4.0mmol) and KOH (2.3g, 40mmol)were dissolved in o-x1ylene (50mL). The mixture was heated to reflux for 8h under nitrogen. After the reaction had all reacted, the mixture was allowed to cool to room temperature and then CH2Cl2 (50mL) was poured into the mixture. The organic layer was dried over anhydrous MgSO4 and concentrated this by a rotary evaporator. The crude materials were purified by silica gel column chromatography (petroleum ether/CH2Cl2=4: 1 v/v) to obtain a white solid 1.5g, 39percent. 1H NMR (400MHz, DMSO-d6, TMS) δ: 8.25 (d, J=7.6Hz, 2H), 8.00 (dd, J=8.0, 1.2Hz, 1H), 7.68 (m, 2H), 7.62–7.56 (m, 1H), 7.45–7.38 (m, 2H), 7.32–7.25 (m, 2H), 7.00 (d, J=8.0H, 2H). 13C NMR (126MHz, CDCl3) δ: 140.84, 140.49, 134.25, 131.16, 130.64, 130.17, 129.78, 128.83, 125.94, 123.24, 120.36, 119.99, 110.14, 110.03. HRMS (m/z): [M+H] calcd for C18H12BrN, 322.0231; found, 322.0250.

Reference: [1] Patent: CN106674083, 2017, A, . Location in patent: Paragraph 0014; 0015
[2] Chemical Communications, 2011, vol. 47, # 17, p. 5079 - 5081
[3] Chemistry - A European Journal, 2016, vol. 22, # 29, p. 10136 - 10149
[4] Dyes and Pigments, 2017, vol. 136, p. 255 - 261
[5] Patent: KR2015/2243, 2015, A, . Location in patent: Paragraph 0040-0043
[6] Patent: CN107417676, 2017, A, . Location in patent: Paragraph 0039; 0040
[7] Dyes and Pigments, 2016, vol. 126, p. 296 - 302
[8] Journal of Materials Chemistry C, 2015, vol. 3, # 48, p. 12529 - 12538
[9] Dyes and Pigments, 2016, vol. 134, p. 562 - 568
[10] Dyes and Pigments, 2017, vol. 140, p. 399 - 406
  • 2
  • [ 583-55-1 ]
  • [ 86-74-8 ]
  • [ 902518-11-0 ]
YieldReaction ConditionsOperation in experiment
85% With copper(l) iodide; potassium carbonate In 5,5-dimethyl-1,3-cyclohexadiene for 12 h; Inert atmosphere; Reflux 20 g (119.61 mmol) of carbazole, 67.68 g (239.22 mmol) of 2-bromoidobenzene, 11.40 g (59.81 mmol) of copper iodide, and 33.06 g (239.22 mmol) of potassium carbonate were dissolved in xylene in a nitrogen atmosphere, and the mixture was refluxed while stirring. After 12 hours, the mixture was cooled to room temperature, distilled water was added thereto, and the mixture was subjected to extraction using methyl chloride (MC), dried using magnesium sulfate, and distilled under reduced pressure. The resultant was separation-purified using column chromatography to obtain 32.64 g (101.67 mmol, 85percent yield) of Intermediate 1-1.
56% With copper(l) iodide; potassium carbonate In 5,5-dimethyl-1,3-cyclohexadiene for 48 h; Inert atmosphere; Reflux (1) In the reaction flask carbazole 3.0g, o-bromo-iodobenzene 10.15g, 2.39 g copper iodide, 4.95g of potassium carbonate and 40mL of dry xylene, the reaction was refluxed for 48 hours nitrogen, was added 50mL of water quench off the reaction, extracted with dichloromethane, the solvent was evaporated, purified by column chromatography, a white precipitate was finally obtained 9- (2-bromophenyl) -9H- carbazole 2.5g, 56percent yield.
47% With copper(l) iodide; potassium carbonate In N,N-dimethyl-formamide at 140℃; for 48 h; Carbazole (1 eq) and o-bromoiodobenzene (3 eq) cuprous iodide (0.05 eq); 11 g potassium carbonate (4 eq) was added to a three-neck bottle.Add anhydrous N,N-dimethylformamide (DMF) and react at 140 ° C for 48 h.After the reaction was completed, the reaction system was poured into water to precipitate a large amount of solid, and the solid was dissolved in dichloromethane, and the mixture was applied to a white solid (47percent);
29% With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 100℃; for 20 h; Inert atmosphere; Reflux Sigma aldrich in nitrogen (http://www. Sigmaaldrich. Com /) carbazole yarn (50 g, 299. 0 mmol) of toluene 0. 5 L senses a rotation velocity of the disk to, herein 1-bromo-2-iodobenzene sigma aldrich yarn (101. 5 g, 358. 8 mmol), bis (dibenzylideneacetone) palladium (0) (5. 16 g, 8. 97 mmol), tris-tert butylphosphine (3. 02 g, 15. 0 mmol) and sodium tert-butoxide (34. 5 g, 358. 8 mmol) in 100 °C sequentially and at the reflux by heating at a 20. Complete after reaction solution at a water doesn't have any error frames, then dichloromethane (DCM) extraction of water to the MgSO4 anhydride after triggers number, filter and was, concentrating it under reduced pressure. Thus-obtained residue number intermediate that is forward separated into flash column chromatography I-3 (27. 9 g, 29percent) a obtained.
25% With potassium carbonate In xyleneHeating / reflux Carbazole (1.672 g, 10 mmol), l-bromo-2-iodobenzene (1.5 ml, 12 mmol), potassium carbonate (K CO , 2.7646 g, 20 mmol), copper iodide (CuI, 95 mg, 0.5 mmol), and 25 ml of xylene were refluxed in a nitrogen atmosphere. After cooling to normal temperature was conducted, a product was extracted with ethyl acetate, water was removed with anhydrous magnesium sulfate (MgSO ), and the solvent was removed at a reduced pressure. The resulting product was passed through a silica gel column using a hexane solvent to produce a compound, the solvent was removed at a reduced pressure, and vacuum drying was conducted to produce the resulting white solid compound of Formula a (800 mg, yield 25percent).[123] MS: [M+H]+ = 323.
25% With potassium carbonate In xyleneReflux; Inert atmosphere Preparation Example 1Preparation of Starting Material Represented by Formula aCarbazole (1.672 g, 10 mmol), 1-bromo-2-iodobenzene (1.5 ml, 12 mmol), potassium carbonate (K2CO3, 2.7646 g, 20 mmol), copper iodide (Cud, 95 mg, 0.5 mmol), and 25 ml of xylene were refluxed in a nitrogen atmosphere. After cooling to normal temperature was conducted, a product was extracted with ethyl acetate, water was removed with anhydrous magnesium sulfate (MgSO4), and the solvent was removed at a reduced pressure. The resulting product was passed through a silica gel column using a hexane solvent to produce a compound, the solvent was removed at a reduced pressure, and vacuum drying was conducted to produce the resulting white solid compound of Formula a (800 mg, yield 25percent).MS: [M+H]+=323.
25% With potassium carbonate In xyleneReflux; Inert atmosphere Preparation Example 1Preparation of Starting Material Represented by Formula aCarbazole (1.672 g, 10 mmol), 1-bromo-2-iodobenzene (1.5 ml, 12 mmol), potassium carbonate (K2CO3.2.7646 g, 20 mmol), copper iodide (CuI, 95 mg, 0.5 mmol), and 25 ml of xylene were refluxed in a nitrogen atmosphere. After cooling to normal temperature was conducted, a product was extracted with ethyl acetate, water was removed with anhydrous magnesium sulfate (MgSO4), and the solvent was removed at a reduced pressure. The resulting product was passed through a silica gel column using a hexane solvent to produce a compound, the solvent was removed at a reduced pressure, and vacuum drying was conducted to produce the desired white solid compound (800 mg, yield 25percent).MS: [M+H]+=323.
25% With copper(l) iodide; potassium carbonate In N,N-dimethyl acetamide at 130℃; for 48 h; Inert atmosphere General procedure: A mixture of carbazole(1.67 g, 10 mmol), 2-bromoiodobenzene (4.2 g, 15 mmol), K2CO3 (2.76 g, 20 mmol), CuI (0.95 g, 5 mmol) and DMA (100 mL) in a 250 mL three-necked flask was heated at 130 °C for 48 h under nitrogen. After cooling, it was poured into water (200 mL) and extracted with CH2Cl2, the combined organic phase was washed with water and dried over MgSO4. After workup, the crude product was isolated by column chromatography (PE) to afford white powder (1.5 g, 25 percent); Rf = 0.26 (PE); M. p.: 110 – 112 °C; 1H NMR (CDCl3, 500 MHz) δ: 8.17(d, J = 7.7 Hz, 2H), 7.88 (d, J = 8.0 Hz, 1H), 7.52 (m, 2H), 7.43 (m, 3H), 7.31 (t, J = 7.33 Hz, 2H), 7.08 (d, J = 8.1 Hz, 2H); 13C NMR (CDCl3, 125 MHz) δ: 140.84, 136.77, 134.23, 131.13, 130.14, 128.80, 125.92, 123.85, 123.25, 120.33, 119.98, 110.01.
25.5% With copper(l) iodide; potassium carbonate In 5,5-dimethyl-1,3-cyclohexadiene at 120℃; Carbazole (7.39 g, 0.0442 mol), 1-bromo-2-iodobenzene (25 g, 0.0883 mol), CuI (0.421 g, 2.22 mmol), K2CO3 (12.12 g, 0.0883 mol) in a 500 mL 2-neck flask Mol) were dissolved in xylene and refluxed and stirred at 120 ° C. The mixture was cooled to room temperature, extracted with CH2Cl2, dried over MgSO4, and then the solvent was removed. Hexane solvent to obtain 3.63 g (25.5percent) of a white solid.
25% With copper(l) iodide; potassium carbonate In 5,5-dimethyl-1,3-cyclohexadieneInert atmosphere; Reflux Under nitrogen atmosphere, a mixture of carbazole (1.7 g), 1-bromo-2-iodobenzene (1.5 ml), potassium carbonate (2.8 g), copper iodide (95 mg), and xylene (25 ml) was refluxed. After cooling to ordinary temperature, the reaction product was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and then, the solvent was removed under reduced pressure. The residue was passed through a silica gel column by using a hexane solvent, and then, the solvent was removed under reduced pressure. The obtained residue was vacuum-dried to obtain the intermediate a as a white solid (800 mg, 25percent yield). MS: [M+H]+=323
25% With copper(l) iodide; potassium carbonate In 5,5-dimethyl-1,3-cyclohexadieneInert atmosphere; Reflux Under nitrogen atmosphere, a mixture of carbazole (1.7 g), 1-bromo-2-iodobenzene (1.5 ml), potassium carbonate (2.8 g), copper iodide (95 mg), and xylene (25 ml) was refluxed. After cooling to ordinary temperature, the reaction product was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and then, the solvent was removed under reduced pressure. The residue was passed through a silica gel column by using a hexane solvent, and then, the solvent was removed under reduced pressure. The obtained residue was vacuum-dried to obtain the intermediate a as a white solid (800 mg, 25percent yield). MS: [M+H]+=323
25% With copper(l) iodide; potassium carbonate In 5,5-dimethyl-1,3-cyclohexadieneReflux; Inert atmosphere Carbazole (1.7 g),1-bromo-2-iodobenzene (1.5 ml),Potassium carbonate (2.8 g),Copper iodide (95 mg) and xylene (25 ml) were refluxed under an atmosphere of nitrogen.After cooling to normal temperature, the product was extracted with ethyl acetate.After drying the extract with anhydrous magnesium sulfate,The solvent was removed under reduced pressure.Passed through a silica gel column using a hexane solvent, the solvent was removed under reduced pressure,The obtained residue was dried under vacuum to obtain an intermediate a (800 mg, 25percent yield) as a white solid.

Reference: [1] Patent: US9853222, 2017, B2, . Location in patent: Page/Page column 66; 67
[2] Chemical Communications, 2014, vol. 50, # 99, p. 15760 - 15763
[3] Organic Electronics: physics, materials, applications, 2011, vol. 12, # 6, p. 1025 - 1032
[4] Patent: CN103588770, 2016, B, . Location in patent: Paragraph 0041
[5] Patent: CN108285452, 2018, A, . Location in patent: Paragraph 0035; 0064; 0073; 0074
[6] Tetrahedron, 2010, vol. 66, # 36, p. 7295 - 7301
[7] RSC Advances, 2015, vol. 5, # 64, p. 51512 - 51523
[8] Patent: KR2016/91198, 2016, A, . Location in patent: Paragraph 0217
[9] Patent: WO2008/66358, 2008, A1, . Location in patent: Page/Page column 47
[10] Patent: US2010/65828, 2010, A1, . Location in patent: Page/Page column 115
[11] Patent: US2010/65827, 2010, A1, . Location in patent: Page/Page column 115
[12] Tetrahedron Letters, 2012, vol. 53, # 39, p. 5248 - 5252
[13] Patent: KR2015/30309, 2015, A, . Location in patent: Paragraph 0069-0072
[14] Patent: US2018/182974, 2018, A1, . Location in patent: Paragraph 0189-0191
[15] Patent: US2018/179206, 2018, A1, . Location in patent: Paragraph 0212-0213
[16] Patent: JP2018/108939, 2018, A, . Location in patent: Paragraph 0227-0228
[17] Patent: JP5663566, 2015, B2, . Location in patent: Paragraph 0163
  • 3
  • [ 1072-85-1 ]
  • [ 86-74-8 ]
  • [ 902518-11-0 ]
YieldReaction ConditionsOperation in experiment
87% With caesium carbonate In N,N-dimethyl-formamide at 150℃; for 24 h; General procedure: A mixture of a fluorinated aryl halide (2.0 mmol), a carbazole (0.5 mmol), and a base (2.0 mmol) in solvent (2 mL) was allowed to react under air atmosphere. The reaction mixture was heated to the specified temperature for 24 h. After reaction completion, the mixture was added to brine (15 mL) and extracted with CH2Cl2 (3 × 15 mL). The combined extract was concentrated under reduced pressure and the product was isolated by short chromatography on a silica gel (200–300 mesh) column.
Reference: [1] Synthesis (Germany), 2016, vol. 48, # 5, p. 737 - 750
[2] Journal of Materials Chemistry C, 2018, vol. 6, # 15, p. 4300 - 4307
  • 4
  • [ 86-74-8 ]
  • [ 583-53-9 ]
  • [ 1150-62-5 ]
  • [ 902518-11-0 ]
YieldReaction ConditionsOperation in experiment
60% With copper(I) oxide; potassium phosphate; N,N`-dimethylethylenediamine In 5,5-dimethyl-1,3-cyclohexadiene at 170℃; for 24 h; Inert atmosphere To a 500 mL four-necked round-bottomed flask, a three-way stopcock, a mechanical stirrer, a condenser, and a thermometer were attached, and the inside was purged with nitrogen. To this flask, carbazole (19.4 g, 116. 3 mmol, 1.0 eq.), 1,2-dibromobenzene (54.8 g, 232.6 mmol, 2.0 eq.), xylenes (120 mL), copper (I) oxide (3.3 g, 23.3 mmol, 0.2 eq.), N,N'-dimethylethylenediamine (5.0 mL, 46.5 mmol, 0.4 eq.), and potassium phosphate (54.3 g, 255.9 mmol, 2.2 eq.) were sequentially added, and the obtained suspension was stirred at 170°C for 24 hours.
Reaction conversion: 80.2percent.
Note that no improvement in conversion was observed, even when the reaction time was extended further.
(Post Treatment and Purification) After the reaction mixture had been cooled to room temperature, toluene and a 28percent aqueous ammonia solution were added to the mixture.
The mixture was transferred to a separating funnel, shaken and allowed to stand, and the layers were separated.
The organic layer was washed five times with a 28percent aqueous ammonia solution (each time the washing was repeated, the blue color of the aqueous layer faded), once with water, and three times with a 1 N aqueous hydrochloric acid solution (hardly soluble black tar was formed in each of the organic layer and the aqueous layer).
The organic layer was concentrated, and the obtained residue was purified by conducting silica gel column chromatography (Eluent: n-hexane/toluene=10/1 to 2/1) three times (because column fractions containing by-products were purified repeatedly) to give 22.5 g of title compound (7) as a pale yellow solid.
Isolated Yield: 60.0percent.
Note that 3.9 g of a by-product, N-phenylcarbazole, was obtained as a colorless solid.
Isolated Yield: 13.8percent.
1H NMR (300 MHz, deuterated chloroform (hereinafter, abbreviated as CDCl3)): δ=8.15 (d, J=7.8 Hz, 2H), 7.85 (dd, J=1.5, 8.1 Hz, 1H), 7.56-7.35 (m, 5H), 7.29 (dt, J=0.9, 6.9 Hz, 2H), 7.06 (d, J=8.1 Hz, 2H).
13C NMR (75 MHz, CDCl3): δ=140.8, 136.7, 134.2, 131.1, 130.1, 128.8, 125.9, 123.8, 123.2, 120.3, 120.0, 110.0.
Reference: [1] Patent: EP2937355, 2015, A1, . Location in patent: Paragraph 0054-0058
  • 5
  • [ 583-55-1 ]
  • [ 86-74-8 ]
  • [ 902518-11-0 ]
Reference: [1] Patent: EP2927234, 2015, A1, . Location in patent: Paragraph 0087
  • 6
  • [ 615-36-1 ]
  • [ 902518-11-0 ]
Reference: [1] Tetrahedron Letters, 2012, vol. 53, # 39, p. 5248 - 5252
Historical Records