[ CAS No. 1592-95-6 ]

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2D
Chemical Structure| 1592-95-6
Chemical Structure| 1592-95-6
Structure of 1592-95-6

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Purity: {[proInfo.showProBatch.pb_purity]}

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Product Details of [ 1592-95-6 ]

CAS No. :1592-95-6MDL No. :MFCD00222621
Formula :C12H8BrNBoiling Point :409.2°C at 760 mmHg
Linear Structure Formula :C12H8NBrInChI Key :-
M.W :246.10Pubchem ID :252446
Synonyms :

Computed Properties of [ 1592-95-6 ]

TPSA : 15.8 H-Bond Acceptor Count : 0
XLogP3 : - H-Bond Donor Count : 1
SP3 : 0.00 Rotatable Bond Count : 0

Safety of [ 1592-95-6 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1592-95-6 ]

  • Upstream synthesis route of [ 1592-95-6 ]

[ 1592-95-6 ] Synthesis Path-Upstream   1~24

  • 1
  • [ 86-74-8 ]
  • [ 1592-95-6 ]
YieldReaction ConditionsOperation in experiment
95% With N-Bromosuccinimide In tetrahydrofuran at 25℃; The intermediate F was synthesized through Reaction Scheme 3A below as follows: 8.708 g (50.00 mmol) of carbazole, 8.899 g (50.00 mmol) of NBS and 100 ml of THF were stirred at room temperature (about 25° C.) to obtain 11.70 g of Intermediate F with a yield of 95percent. (0152) 1H-NMR (300 MHz, CDCl3): δ=11.701 (br, 1H), 8.205 (d, 1H), 8.015 (s, 1H), 7.504-7.201 (m, 5H) (0153) 13C-NMR (75 MHz, CDCl3): δ=135.4, 131.4, 124.0, 122.2, 121.1, 121.0, 120.1, 118.9, 113.3, 111.1 (0154)
95% With N-Bromosuccinimide In N,N-dimethyl-formamide at -10℃; Inert atmosphere First, carbazole (16.7 g, 100.0 mmol)Placed in 250mL external constant pressure dropping funnel single-ported bottle A,Vacuum, nitrogen cycle three times,After adding 50mLDMF dissolved,The single-necked flask A was placed in ice-salt bath (ice volume ratio:Saline saturated solution = 10: 1,Temperature is about -10 ° C)After full cooling,NBS (17.7 g, 100.0 mmol)DMF solution was slowly added dropwise to the carbazole solution through a constant pressure dropping funnel.Drip and add ice salt bath,Keep cold.Device does not move,Reaction 18-24h.After the reaction is completed,Pour into a large amount of water sedimentation,After filtration take the solid,Ethanol recrystallized.(The solid and a small amount of ethanol was heated to boiling,If there is still a lot of solid,Then continue to add ethanol,Until completely dissolved - at this time directly placed cooling recrystallization or only a small amount of solid - at this time filtered hot cooling recrystallization,Recrystallization can be added 2/3 amount of water) Yield: 95percent.
91% With N-Bromosuccinimide In tetrahydrofuran at 0 - 20℃; for 12.00 h; The 16.7g (0.1mol) carbazole was dissolved in tetrahydrofuran (THF, 500mL) in, and then the resulting solution was stirred at 0 10 minutes. Thereto was added N- bromosuccinimide (NBS, 18.68g, 0.105mol), the resulting mixture was stirred at normal temperature for 12 hours, then extracted with ethyl acetate and distilled water. The organic layer was dried over anhydrous magnesium sulfate (MgSO4) was dried, then the solvent was removed, and subjected to silica gel column chromatography to give 22.4g (91percent) Compound A-1.
87% at 50℃; for 2.00 h; General procedure: In a round-bottomed flask, the substrate (1 mmol) and aqueous HBr(48percent) (1 mL) were mixed in DMSO (1 mL). The mixture was stirredat corresponding temperature for 1–4 h. After cooling to roomtemperature, the reaction was adjusted to pH 7–8 with aqueous NaOHsolution (4 M). Then the mixture was washed twice with EtOAc, andthe combined organic extracts were dried, filtered and concentratedunder reduced pressure to give bromination products.
86.1% With N-Bromosuccinimide In tetrahydrofuran at 20℃; for 5.00 h; A mixture of carbazole (1, 52.6 mmol) and N-bromosuccinimide (50.0 mmol) in tetrahydrofuran (100 mL) was stirred at room temperature for 5 h. The reaction mixture was evaporated under reduced pressure and the resulting residue was purified by crystallization from hexane-acetone mixture to obtain 3-bromo-9H-carbazole (5).Yield 86.1 percent; White solid, mp: 194.4 , Rf = 0.34 (5:1 n-hexane-ethyl acetate); 1H NMR (400 MHz, DMSO-d6): δH 7.14-7.18 (m, 1H), 7.38-7.49 (m, 4H), 8.15 (d, J = 8.0 Hz, 1H), 8.34 (s, 1H), 11.41 (s, 1H)
85% With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 2.00 h; Carbazole (8.25 g, 0.05 mol) was added into 50 ml of DMF anddissolved in stirring. Then the mixed solution of N-bromosuccinimide(NBS) (8.90 g, 0.05 mol) and 50 ml of DMF was added dropwiseinto reaction flask in ice-water bath. The mixture wasstirred at room temperature for 2 h. The solution was poured into500 ml of ice water and the white precipitate was filtered, washedby distilled water, recrystallized by ethanol and dried under vacuum. white powder (10.45 g, 85percent) was obtained. 1H NMR(CDCl3, d, ppm): 8.13 (s, 2H), 7.52-7.54 (d, 2H), 7.31-7.35 (d, 3H).
85% With N-Bromosuccinimide In N,N-dimethyl-formamideCooling with ice Carbazole (1.002 g, 5.997 mmol) was added into DMF solution (50 mL). Then the mixture of N-bromosuccinimide (NBS) (1.068 g, 6.000 mmol) and DMF (20 mL) was added dropwise into reaction flask in ice-water bath. After filtration and washed by water, white powder was obtained [29] (1.254 g, 85.0percent). Mp: 199 °C. 1H NMR (CDCl3, 400 MHz, TMS) δ: 11.40 (s, 1H), 8.33 (d, J = 8.4 Hz, 1H), 8.12 (d, J = 8.4 Hz, 1H), 7.43 (m, 4H), 7.15 (t, J = 7.6 Hz, 1H).
72% With N-Bromosuccinimide In N,N-dimethyl-formamide at 0 - 20℃; for 2.00 h; 3-Bromocarbazole (1 ). To DMF (67 ml) was added carbazole (10 g, 59.80 mmol) and mixture was stirred at room temperature for 15 minutes. N-bromosuccinimide (10.6 g, 59.56 mmol) in DMF (100 ml) was added dropwise at 0°C. The mixture was allowed to warm to room temperature and stirred for two hours. White precipitates were formed after the mixture was poured into water. The precipitates were filtered and dissolved in dichloromethane. The organic layer was washed with water to remove water soluble impurities. The organic fraction was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The resulting white solid was purified by recrystallization from ethanol to give colorless crystals (10.65 g, 72 percent yield). 1H-NMR (CDCIs, 400 MHz): δ 8.34(bs, 1 H), 8.15(d, J=7.8Hz, 1 H), 7.48(d, J=8.2, 1 H), 7.45(m, 1H), 11.42(s, 1H). (MS, ESI) m/z 246 (M+).
71% With N-Bromosuccinimide; silica gel In dichloromethane at 10 - 20℃; for 42.00 h; Carbazole (52.26 g, 0.30 mol) was dissolved in dichloromethane (3 L) and silicagel (60 mesh, 600 g) was added to the mixture and the mixture was cooled to 10 0C. A mixture of Λ/-bromosuccinimide (NBS, 55 g, 0.30 mol) in dichloromethane (400 ml_) was added at 10 0C. After addition, the mixture was allowed to reach room temperature. After standing for 42 hours, the mixture was filtered, and the solid was washed with dichloromethane (4 x 200 ml_), the combined filtrates were washed with water (300 ml_) and dried over Na2SO4 . Evaporation in vacuo to dryness afforded 77 g of crude product. Recrystallization from 2-propanol (800 ml_) afforded 71 percent 3-bromocarbazole.
68% With N-Bromosuccinimide In acetonitrile at 20℃; for 1.00 h; In the procedures shown in Scheme 1, the preparation of 3-bromocarbazole 1 using N-bromosuccinimide was contaminated by some starting material and 3,6-dibromocarbazole, both of which could be removed by fractional recrystallization from toluene. The preparation of 3 was accomplished in good yield by dropwise introduction of the lithiated TBDMS-protected 3-bromocarbazole 2 intermediate to excess 1,4-diiodobutane.
67% With N-Bromosuccinimide In acetic acid monohydrate at 20℃; for 15.00 h; [Step 1: Synthesis of 3-bromo-9H-carbazole]
32 g (0.19 mmol) of 9H-carbazole was put into a 2 L Erlenmeyer flask, and then ether acetate (1.2 L) was added thereto so that the 9H-carbazole was dissolved in the ether acetate.
To this solution was added 34 g (0.19 mol) of N-bromosuccinimide (NBS), and the mixture was stirred for about 15 hours in the air at room temperature.
After the stirring, water was added to the mixture so that the precipitate was dissolved in the mixture.
The organic layer of this mixture was washed with water three times and then with a saturated saline solution once.
Magnesium sulfate was added so that the organic layer was dried.
After the drying, the mixture was subjected to gravity filtration.
The obtained filtrate was condensed to give a white solid.
The obtained solid was recrystallized with ether acetate/hexane to give 36 g of a white powdered solid, which was the object of the synthesis, at a yield of 67 percent.
A synthesis scheme of Step 1 is shown in (c-1) given below.
67.6% With N-Bromosuccinimide In N,N-dimethyl-formamide at -10 - -5℃; (1) Carbazole (16.7 g, 100 mmol) was dissolved in 100 mL of DMF,In a 500 mL four-necked flask was mechanically stirred,The temperature was controlled with an ice-salt bath-5 ° C to -10 ° C,Further, 100 mL of a DMF solution of NBS (18.7 g, 105 mmol) was added,Stirring was continued and the reaction was continued overnight.The reaction was poured vigorously into water, stirred, filtered and the filter cake was allowed to dry. Ethyl acetate,To give 16.6 g of 3-bromocarbazole in 67.6percent yield.
59% With N-Bromosuccinimide In acetonitrile at 0 - 20℃; Inert atmosphere To a suspension of 9.153 g (54.7 mmol) of carbazole in 100 ml of HPLC grade acetonitrile at O0C was slowly added 10.433 g (58.6 mmol) of N- bromosuccinimide (NBS) under vigorous stirring. After the NBS was added, the contents of the flask's were slowly brought to room temperature and stirred overnight. A bulky white precipitate was filtered, washed with cold acetonitrile (2x30 ml) and hexane (2x50 ml), and dried under vacuum to constant weight to yield 7.95 g (59percent yield) of 3-bromocarbazole 4 as a fluffy white solid. Additional product can be isolated from the filtrate (Rf = 0.26 for carbazole and Rf = 0.16 for 3-bromocarbazole 4 in EtOAc/hexane = 85:15).
58.04% With N-Bromosuccinimide In N,N-dimethyl-formamide at 0℃; for 12.00 h; [169] Carbazole (20 g, 119.6 mmol) was dissolved in dimethylformamide (DMF) 200 mL, and N-bromosuccinimide (NBS) (21.2 g, 119.6 mmol) was added at 0°C. After stirring for 12 hours, distilled water was added, and the obtained solid was filtered under reduced pressure. The obtained solid was added to methanol, and after stirring, the solution was filtered under reduced pressure. The re-obtained solid was added to ethyl acetate (EA) and methanol, and stirred. Then, the mixture was filtered under reduced pressure to obtain compound 1-6 (17 g, 69.07 mmol, 58.04 percent).
58.04% With N-Bromosuccinimide In N,N-dimethyl-formamide at 0℃; for 12.00 h; After dissolving carbazole 20 g (119.6 mmol) in dimethylfomiamide (DMF) 200 mL, N-bromosuccineimide (NBS) 21.2 g (119.6 mmol) was added to the mixture at 0°C. After stirring the mixture for 12 hours, distilled water was added to the mixture, and the produced solid was filtered under reduced pressure. The obtained solid was added to methanol, and the mixture was stuffed, and filtered under reduced pressure. Then, the obtained solid was added to a mixture of EA, and methanol, the mixture was stilTed, and filtered under reduced pressure to obtain compound C-3-2 17 g (58.04 percent).
53% With N-Bromosuccinimide In acetonitrile at 20℃; for 16.00 h; N-Bromosuccinimide (21 .63 g, 121 .53 mmol) was added portionwise to a stirred solution of 9 - -carbazole (19.00 g, 1 13.6 mmol) in acetonitrile (420 ml_) at room temperature. The reaction mixture was stirred at room temperature for 16 hours. After complete consumption of the starting material, as indicated by TLC, the reaction mixture was precipitated and filtered. The precipitate was washed with n-pentane to afford 3- bromo-9 - -carbazole as an off-white solid (14.7 g, 53percent). 1 H NMR (400 MHz, CDCI3): δ 8.19 (br s, 1 H), 8.05-7.97 (m, 2H), 7.54-7.40 (m, 3H), 7.32-7.25 (m, 2H). LCMS: m/z 244.03, 246.03 [M-H]".
51% With N-Bromosuccinimide In N,N-dimethyl-formamide at 0℃; Synthesis of 3-bromocarbazole. NBS (12.77 g, 71.8 mmol) in DMF was added to 9H-carbazole (12 g, 71.8 mmol) in 200 mL at 0 °C dropwise. The reaction was monitored by HPLC. After 2 h, HPLC indicated 76percent of desired product and 6percent of dibrominated compound. The reaction was quenched by adding 500 mL of ice water. The internal temperature was controlled to be lower than 10 °C. The precipitate formed was collected by filtration. The solid was stirred in 400 mL of warm methanol. (-40 °C). The solid was collected by filtration. The solid was dissolved in 150 mL of DCM. 200 mL of methanol was added. The DCM was boiled off. The solvent level was down to 150 mL. The slurry was stirred at room temperature overnight. The solid was collected by filtration. 9 g (51percent yield) of solid was collected.
47% With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; A solution of N-bromosuccinimide (10.64 g, 59.8 mol) dissolved in NN-dimethylformamide (DMF) (20 ml) was treated with a constant pressure dropping solution The funnel was added dropwise to a solution of carbazole (10 g, 59.8 mol) in DMF (20 ml)in. After completion of the drop, the ice bath was removed and the reaction was conducted overnight at room temperature. The reaction solution was then washed with deionized water, the solid was precipitated, and the solid was filtered off and the product was recrystallized from ethanol (2). Yield: 47percent.
20 g With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; 16 g (grams) of carbazole was dissolved in 80 mL ) n, n ′-dimethylformamide, to this was added 18 g n-bromosuccinimide, and the reaction was stirred at room temperature overnight. The reaction mixture was poured into water and the precipitate filtered. a white solid, washed with methanol and dried under vacuum to obtain 20 g of 3-bromocarbazole.

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  • 2
  • [ 105971-15-1 ]
  • [ 1592-95-6 ]
YieldReaction ConditionsOperation in experiment
79% With triphenylphosphine In 1,2-dichloro-benzeneInert atmosphere; Reflux Under nitrogen atmosphere, intermediate F 2.78g (10 mmol) was dissolved in o- dichlorobenzene 20ml and triphenylphosphine 6.56g (25mmol) was added and reflux. After completion of the reaction, MC 200ml, H2O 200ml was added and then the the MC layer was extracted, concentrated and separated by column chromatography using Hex : EA =5 : 1 and dried over anhydrous MgSO4 to give the intermediate G 1.94g (79percent).
79% With triphenylphosphine In 1,2-dichloro-benzeneInert atmosphere; Reflux Intermediate E 2.78g (10mmol) was dissolved in o-dichlorobenzene 40ml under nitrogen, triphenylphosphine 6.56g (25mmol) was added and the mixture was refluxed. After completion of the reaction, 200ml MC and 200ml H2O was added, the MC layer was extracted and dried over anhydrous MgSO4 and concentrated by column with Hex: EA = 5: 1 to give the intermediate F 1.94 g(79percent).
79% With triphenylphosphine In 1,2-dichloro-benzeneInert atmosphere; Reflux Then dissolved under nitrogen the intermediates B 2.78g (10mmol) in 20ml o-dichlorobenzene triphenylphosphine 6.56g (25mmol) and the mixture was refluxed.To 1: After completion of the reaction, 200ml MC, the MC layer then was extracted by the addition of 200ml H2O and dried over anhydrous MgSO4 and concentrated to Hex: MC = 5Column with intermediate CTo give a 1.94g (79percent).
79% With triphenylphosphine In 1,2-dichloro-benzeneInert atmosphere; Reflux Synthesis of Intermediate 27 (0166) (0167) Under a nitrogen atmosphere, Intermediate 26 (2.78 g, 10 mmol) was dissolved in o-DCB (40 mL), and then triphenylphosphine (6.56 g, 25 mmol) was added dropwise and refluxed. (0168) After the reaction was terminated, MC (200 mL) and H2O (200 mL) were added. The MC layer was extracted, dried over anhydrous magnesium sulfate, concentrated, and purified by column chromatography eluting with Hex:MC=5:1, to obtain Intermediate 27 (1.94 g, 79percent). (0169) Intermediate 27 MS(FAB): 246(M+)
79% With triphenylphosphine In 1,2-dichloro-benzeneInert atmosphere; Reflux Under a nitrogen atmosphere, Intermediate 22 (2.78 g, 10 mmol) was dissolved in o-DCB (40 mL), and then triphenylphosphine (6.56 g, 25 mmol) was added and refluxed. After the reaction was terminated, MC (200 mL) and H2O (200 mL) were added. The MC layer was extracted, dried over anhydrous magnesium sulfate, concentrated, and purified by column chromatography eluting with Hex:MC=5:1, to obtain Intermediate 23 (1.94 g, 79percent).
77% With triphenylphosphine In 1,2-dichloro-benzene at 200℃; The intermediate F 1mol Was dissolved in o-dichlorobenzene was added to 2.5mol and triphenylphosphine at 200°C It was stirred. After completion of reaction, after the removal o-dichlorobenzene by distillation and extracted with water and CH2Cl2 and the organic layer no It is dried with MgSO4, and concentrated by column chromatography and recrystallization to the resulting product and then to obtain the desired intermediate G (Yield: 77percent).
74% With triphenylphosphine In 1,2-dichloro-benzene at 200℃; Said Sub 1-I-1 obtained in the synthesis (168.52g, 606mmol) senses a rotation velocity of the disk to in round bottom flasko- dichlorobenzene in a, triphenylphosphine (397.35g, 1514.9mmol) adding an 200 °C stirring section. When reaction is completed the via fractional distillation to remove the dichlorobenzene- o 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 110.36g (yield: 74percent)is obtained.
60% With triphenylphosphine In 1,2-dichloro-benzene at 200℃; Wherein the Sub 1-I-1 (66.39 g, 238.7mmol) after a round bottom flask was dissolved in o-dichlorobenzene (1194ml),it was added triphenylphosphine (156.54 g, 596.8 mmol) and stirred at 200 . After completion ofreaction was removed by distillation and the o-dichlorobenzene and water,extracted CH2Cl2. The resulting compound and the organic layer was dried overMgSO4 and concentrated to silicagel column and the product was recrystallizedfrom 35.25 g (yield: 60percent) was obtained.

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[2] Patent: KR2015/102734, 2015, A. Location in patent: Paragraph 0174-0177
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  • 3
  • [ 21865-50-9 ]
  • [ 1592-95-6 ]
YieldReaction ConditionsOperation in experiment
91% With copper(II) choride dihydrate In dimethyl sulfoxide at 100℃; for 7.00 h; General procedure: A mixture of starting compound (2.69 mmol), CuCl2.2H2O (10 mol percent) in DMSO (5 mL) stirred at 100 °C. The reaction progress was monitored by thin layer chromatography (PMA was used for stain solution). The reaction mixture was poured into ice cold water. The crude product was purified by column chromatography using ethyl acetate and petroleum ether as eluent to afford carbazoles.
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  • [ 108-94-1 ]
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