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Chemical Structure| 54523-47-6 Chemical Structure| 54523-47-6

Structure of 54523-47-6

Chemical Structure| 54523-47-6

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Product Details of [ 54523-47-6 ]

CAS No. :54523-47-6
Formula : C15H12Br2O
M.W : 368.06
SMILES Code : O=C(CC1=CC=C(Br)C=C1)CC2=CC=C(Br)C=C2
MDL No. :MFCD12031109
Boiling Point : No data available
InChI Key :PQDQAUVBWSUMMB-UHFFFAOYSA-N
Pubchem ID :603327

Safety of [ 54523-47-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313

Application In Synthesis of [ 54523-47-6 ]

* 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 [ 54523-47-6 ]

[ 54523-47-6 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 14062-25-0 ]
  • [ 54523-47-6 ]
YieldReaction ConditionsOperation in experiment
82% With sodium hydride; In toluene; at 30 - 78℃; To a slurry of sodium hydride (9.17 grams, 0.23 mole) in 50 milliliters of toluene was added dropwise, a solution of ethyl 4-bromophenylacetate (50 grams, 0.21 mole) in toluene (50 milliliters) at 30-32C. After addition was completed, the reaction mixture was slowly warmed to 50C where the reaction began to rapidly exotherm with evolution of hydrogen gas. The reaction mixture was further heated to 78C for 2 hours, cooled to room temperature and then HCl (45 grams) in water (22.5 grams) was slowly added dropwise to neutralize the solution. The layers were separated and the aqueous phase was extracted with diethylether. The combined organic extracts were dried and the solvent was removed to leave a yellow oil. This oil was refluxed for 24 hours in a mixture of glacial acid (60 milliliters) and concentrated HCl (30 milliliters). After cooling, the layers were separated, and the organic layer solidified to provide a yellow solid. This crude product was recrystallized from n-heptane to give a pure product as a white solid (31.2 grams, 82% isolated yield).
  • 3
  • [ 4755-77-5 ]
  • [ 589-15-1 ]
  • [ 54523-47-6 ]
  • 4
  • [ 201230-82-2 ]
  • [ 589-15-1 ]
  • [ 19829-56-2 ]
  • [ 54523-47-6 ]
  • [ 88364-54-9 ]
  • [ 1878-68-8 ]
  • 5
  • [ 54523-47-6 ]
  • [ 84-11-7 ]
  • [ 131273-92-2 ]
YieldReaction ConditionsOperation in experiment
60% With potassium hydroxide; In ethanol; at 50℃; for 5h; 1000mL, 3-neck round bottom flask, 2,7-dibromo-phenanthrene-9,10-dione 50 g (0.240 mol), 1,3- bis ((4-bromophenyl) propan-2 one was added 500ml of 80g of ethanol and stirred. In the potassium hydroxide (KOH) in 30g of this solution and stirred for 5 hours at 50 C. The resulting solid was filtered off after cooling the reaction solution to room temperature and washed well with methanol. Vacuum drying the solid obtained to give an intermediate A-1 70 g (yield 60%).
60% With potassium hydroxide; In ethanol; at 50℃; for 5h; 50 g (0.240 mol) of 2,7-dibromophenanthrene-9,10-dione, 1,3-bis (4-boromophenyl) propa-2-one (1000 ml, in a three-neck round bottom flask) 80 g of 1,3-bis (4-bromophenyl) propan-2-one) and 500 ml of ethanol were added and stirred. Potassium hydroxide and 30 g of KOH were added to the solution and stirred at 50 C. for 5 hours. After cooling the reaction solution to room temperature, the resulting solid was filtered and washed well with methanol. The obtained solid was dried in vacuo to give 70 g (yield 60%) of the target compound A.
  • 6
  • [ 25424-26-4 ]
  • [ 54523-47-6 ]
  • [ 54523-26-1 ]
  • 9
  • [ 589-15-1 ]
  • /PBSAB018-1380/ [ No CAS ]
  • [ 19829-56-2 ]
  • [ 54523-47-6 ]
  • [ 88364-54-9 ]
  • [ 1878-68-8 ]
  • 11
  • 1-bromo-3,7-dimethyloctane [ No CAS ]
  • [ 54523-47-6 ]
  • [ 347390-22-1 ]
  • 13
  • [ 115-77-5 ]
  • [ 54523-47-6 ]
  • [ 493015-32-0 ]
  • 14
  • [ 54523-47-6 ]
  • [ 501034-27-1 ]
  • 15
  • [ 1878-68-8 ]
  • [ 54523-47-6 ]
YieldReaction ConditionsOperation in experiment
68% With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 24h; The DCC (7. 7g, 37. 3mmol) and DMAP (1. 145g, 9. 35mmol) was dissolved in 75ml of dichloromethane was slowly added dropwise to bromophenylacetic acid (8. 05g, 37. 45mmol) in dichloromethane solution 75ml. After the addition was complete the reaction at room temperature for 24h, the solid was filtered off the reaction, dichloromethane was distilled off under reduced pressure, and recrystallized from ethanol to give white crystals 4. 33g, 68% yield.
60% With dmap; dicyclohexyl-carbodiimide; In dichloromethane; for 24h;Inert atmosphere; (1) Dicyclohexylcarbodiimide (DCC) (6.19 g, 30 mmol) and 4-dimethylaminopyridine (916 mg, 7.5 mmol) were added to the reaction vessel, pumped three times, and 60 mL of dichloromethane was added under a nitrogen atmosphere. A solution of 4-bromophenylacetic acid (Compound 1, 30 mmol) in dichloromethane (60 mL of dichloromethane) was added dropwise, and reacted for 24 hours after the addition was completed. After the reaction, the solvent was concentrated, removed, separated and purified by column chromatography to obtain intermediate product 2 (compound 2). Yield 60%.
45% With dmap; In dichloromethane; at 20℃; for 24h;Inert atmosphere; To a flame-dried apparatus and under argon, a solution of p-bromophenylacetic acid(5.00 g, 23.3 mmol, 2 equiv) in dry DCM (50 mL) was added to a solution of DCC(4.8 g, 23.3 mmol, 2 equiv) and DMAP (709 mg, 5.8 mmol, 0.5 equiv) in dry DCM(50 mL). The reaction mixture was stirred at room temperature for 24 h. The precipitatewas removed by filtration and the filtrate was evaporated in vacuo. The solid wasrecrystallized from methanol to afford 056 as a light orange solid (1.94 g, 45 %).
With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 4h; To a solution of DCC (2.23 g, 10.8 mmol) and DMAP (0.35 g, 2.91 mmol) in anhydrous dichloromethane (50 mL) was slowly added a solution of 2-(4-bromophenyl)acetic acid (366A) (2.0 g, 9.35 mmol) in anhydrous dichloromethane (80 mL). The mixture was stirred at room temperature for 4 hours and concentrated under reduced pressure. The residue was partitioned between EtOAc (50 mL) and water (50 mL). The organic layer was separated, washed with brine (30 mL x 3), dried over anhydrous sodium sulfate, concentrated, and purified with flash column chromatography on silica gel (ethyl acetate in petroleum ether, 0% to 25% v/v) to afford Compound 366B. LC-MS (ESI) m/z: non-ionizable compound under routine conditions used; -NMR (DMSO-^, 400 MHz): d (ppm) 3.87 (s, 4H), 7.13 (d, J= 8.3 Hz, 4H), 7.49 (d, J= 8.3 Hz, 4H).
With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 4h; To a solution of DCC (2.23 g, 10.8 mmol) and DMAP (0.35 g, 2.91 mmol) in anhydrous dichloromethane (50 mL) was slowly added a solution of 2-(4-bromophenyl)acetic acid (366A) (2.0 g, 9.35 mmol) in anhydrous dichloromethane (80 mL). The mixture was stirred at room temperature for 4 hours and concentrated under reduced pressure. The residue was partitioned between EtOAc (50 mL) and water (50 mL). The organic layer was separated, washed with brine (30 mL x 3), dried over anhydrous sodium sulfate, concentrated, and purified with flash column chromatography on silica gel (ethyl acetate in petroleum ether, 0% to 25% v/v) to afford Compound 366B. LC-MS (ESI) m/z: non-ionizable compound under routine conditions used; 1H-NMR (DMSO-d6, 400 MHz): d (ppm) 3.87 (s, 4H), 7.13 (d, J = 8.3 Hz, 4H), 7.49 (d, J = 8.3 Hz, 4H).

References: [1]Doklady Chemistry,2012,vol. 442,p. 23 - 29.
[2]Journal of Organic Chemistry,2003,vol. 68,p. 240 - 246.
[3]Heterocycles,2013,vol. 87,p. 2333 - 2341.
[4]Patent: CN103012098,2016,B .Location in patent: Paragraph 0046; 0047; 0048; 0049.
[5]Chemistry - An Asian Journal,2017,vol. 12,p. 3016 - 3026.
[6]Patent: CN108752249,2018,A .Location in patent: Paragraph 0040; 0043; 0045; 0053; 0056; 0064; 0065; 0074.
[7]Journal of Materials Chemistry C,2017,vol. 5,p. 799 - 802.
[8]Angewandte Chemie - International Edition,2020,vol. 59,p. 5712 - 5720.
    Angew. Chem.,2020,vol. 132,p. 5761 - 5769,9.
[9]Journal of the American Chemical Society,2017,vol. 139,p. 10506 - 10513.
[10]Synthesis,2020,vol. 52,p. 2535 - 2540.
[11]Journal of the American Chemical Society,2011,vol. 133,p. 20962 - 20969.
[12]Turkish Journal of Chemistry,2021,vol. 45,p. 42 - 49.
[13]Chemistry - A European Journal,2012,vol. 18,p. 14745 - 14751.
[14]Chemical Communications,2015,vol. 51,p. 4477 - 4480.
[15]Patent: WO2016/193748,2016,A1 .Location in patent: Page/Page column 22.
[16]Journal of the American Chemical Society,2017,vol. 139,p. 17799 - 17802.
[17]Chemistry Letters,2007,vol. 36,p. 590 - 591.
[18]Journal of Chemical Research,2008,p. 173 - 180.
[19]Patent: EP1476416,2015,B1 .
[20]Patent: WO2019/133770,2019,A2 .Location in patent: Paragraph 001831; 001832; 001833.
[21]Patent: WO2020/257487,2020,A1 .Location in patent: Paragraph 001789; 001790.
[22]Organic Letters,2021,vol. 23,p. 7295 - 7300.
[23]Organic Letters,2021,vol. 23,p. 9425 - 9430.
  • 16
  • [ 589-15-1 ]
  • pentacarbonyliron [ No CAS ]
  • [ 54523-47-6 ]
  • 18
  • [ 54523-47-6 ]
  • [ 1226-42-2 ]
  • [ 870249-44-8 ]
YieldReaction ConditionsOperation in experiment
90% With potassium hydroxide; In ethanol; at 70℃; for 3h;Inert atmosphere; (2) Intermediate product 2 (3.69 g, 10 mmol), 4,4'-dimethoxyphenol ester (Compound 3) (2.7 g, 10 mmol) and potassium hydroxide (0.168 g, 3 mmol) were added to the reaction flask, pumped three times, and solvent ethanol (30mL) was injected under nitrogen protection. The resulting mixture was refluxed at 70 C for three hours. After completion of the reaction, the reaction flask was cooled in an ice bath and precipitated to obtain the product. The product was washed with cold ethanol and dried to give red powder product 4 (compound 4). Yield 90%.
  • 19
  • [ 35578-47-3 ]
  • [ 54523-47-6 ]
  • [ 49764-92-3 ]
YieldReaction ConditionsOperation in experiment
68% With potassium hydroxide; In ethanol; dichloromethane; water; Preparative Example 11 2,3,4,5-Tetra(4-bromophenyl)cyclopentadienone (14) A solution of potassium hydroxide (230 mg, 4.1 mmol) in ethanol (5 cm3) was added to a solution of (13) (3.01 g, 8.2 mmol) and 4,4'-dibromobenzil (3.01 g, 8.2 mmol) in ethanol (45 cm3) at 70 C., and the reaction was stirred at 70 C. for 4 hours. Water (200 cm3) and dichloromethane (200 cm3) were added, and the layers were separated. The organic layer was washed with brine (200 cm3) and dried over magnesium sulfate. The solvent was removed to leave a dark purple solid. The crude product was passed through a plug of silica, and then recrystallized from a dichloromethane/ethanol mixture to give (14) as a dark purple crystalline solid (3.87 g, 68%).
62% With potassium hydroxide; In ethanol; for 0.666667h;Reflux; To a solution of 056 (310 mg, 0.84 mmol, 1 equiv) and 101 (310 mg, 0.84 mmol, 1 equiv) in ethanol (3 mL) was added a solution of KOH (47 mg, 0.84 mmol, 1 equiv) in ethanol (0.5 mL). The reaction mixture was stirred at reflux for 40 mm. The dark redsolution was then cooled down to 0 00. The resulting dark red precipitate was filtered and washed with cold ethanol, affording 102 as dark red crystals (365 mg, 62 %).
After 4,4v-dibromobenzyl (9.8 g, 27 mmol) and di(4-bromophenyl)acetone (2.0 g,5.4 mmol) were dissolved in 40 mL of ethanol and heated, the mixture was refluxed under stirring for 1 hour. KOH (0.3 g, 5.4 mmol) dissolved in 10 mL of ethanol was slowly added dropwise thereto, and then refluxed under stirring for 30 minutes. The resultant was slowly cooled to give a dark red solid powder. The obtained dark red <n="35"/>solid powder was filtered under reduced pressure, and then dried under vacuum to obtain a starting material represented by Formula k. [114] MS [M+H] 700
  • 20
  • [ 54523-47-6 ]
  • [ 6217-22-7 ]
  • [ 908352-01-2 ]
  • 21
  • [ 54523-47-6 ]
  • [ 189619-30-5 ]
  • 2,5-bis(4-bromophenyl)-3,4-(4-triisopropysilylethynylphenyl)cyclopenta-2,4-dien-1-one [ No CAS ]
  • 22
  • [ 589-15-1 ]
  • Na2Fe(CO)4 [ No CAS ]
  • [ 54523-47-6 ]
  • 23
  • [ 54523-47-6 ]
  • [ 134-81-6 ]
  • [ 54523-24-9 ]
YieldReaction ConditionsOperation in experiment
91% With potassium hydroxide; In methanol; dichloromethane; for 1.5h;Inert atmosphere; Reflux; To a solution of <strong>[54523-47-6]1,3-bis(4-bromophenyl)-2-propanone</strong> (3 300 mg, 0.815 mmol) and benzyl (0.815 mmol) in dichloromethane (1.5 mL)(30 mL) was added potassium hydroxide (22.8 mg, 0.407 mmol) as a solution in methanol (3 mL). the reaction was heated to reflux under nitrogen for 90 minutes before cooling in an ice bath. This mixture was introduced into 50 mL of cold methanol, and the obtained solid 2,5-bis(4-bromophenyl)-3,4-diphenylcyclopenta-2,4-dienone (4) was filtered to obtain a dark purple solid (404 mg, 91% yield).
68% After benzyl (1.14 g, 5.4 mmol) and di(4-bromophenyl)acetone (2.0 g, 5.4 mmol) were dissolved in 40 mL of ethanol and heated, the mixture was refluxed under stirring <n="34"/>for 1 hour. KOH (0.3 g, 5.4 mmol) dissolved in 10 mL of ethanol was slowly added drop wise thereto, and then refluxed under stirring for 30 minutes. The resultant was slowly cooled to give a dark red solid powder. The obtained dark red solid powder was filtered under reduced pressure, and then dried under vacuum to obtain a starting material represented by Formula i.[104] (2.0 g, 68 %); 1H NMR (400 MHz, DMSO-J ) 7.50-7.48(d, 4H), 7.30-7.23(m, 6H),7.11-7.09(d, 4H), 6.98-6.96(d, 4H) ; MS [M+H] 540,542,544
  • 24
  • [ 54523-47-6 ]
  • [ 917974-57-3 ]
  • 25
  • [ 54523-47-6 ]
  • C36H23Br5 [ No CAS ]
  • 26
  • [ 54523-47-6 ]
  • 1-bromo-1-(p-tolyl)-2,3,4,5-tetra(4-bromophenyl)cyclopenta-2,4-diene [ No CAS ]
  • 27
  • [ 54523-47-6 ]
  • C36H23Br5 [ No CAS ]
  • 28
  • [ 54523-47-6 ]
  • 9,12-bis-(4-bromo-phenyl)-10-phenanthren-4-yl-benzo[e]pyrene [ No CAS ]
  • 29
  • [ 54523-47-6 ]
  • [ 908352-03-4 ]
  • 31
  • [ 54523-47-6 ]
  • [ 870249-48-2 ]
  • 32
  • [ 54523-47-6 ]
  • [ 870249-47-1 ]
  • 33
  • [ 54523-47-6 ]
  • C90H64N2O4 [ No CAS ]
  • 34
  • [ 54523-47-6 ]
  • C96H76N2O2 [ No CAS ]
  • 35
  • [ 54523-47-6 ]
  • [ 493015-33-1 ]
 

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