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Chemical Structure| 486-25-9 Chemical Structure| 486-25-9
Chemical Structure| 486-25-9

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Synonyms: 9-Fluorenone

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Product Details of Fluorenone

CAS No. :486-25-9
Formula : C13H8O
M.W : 180.20
SMILES Code : O=C1C2=C(C3=C1C=CC=C3)C=CC=C2
Synonyms :
9-Fluorenone
MDL No. :MFCD00001141
InChI Key :YLQWCDOCJODRMT-UHFFFAOYSA-N
Pubchem ID :10241

Safety of Fluorenone

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of Fluorenone

* 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 [ 486-25-9 ]

[ 486-25-9 ] Synthesis Path-Downstream   1~22

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  • [ 13214-64-7 ]
  • [ 19747-05-8 ]
  • 3
  • [ 6050-13-1 ]
  • [ 486-25-9 ]
  • [ 6223-83-2 ]
  • 5
  • [ 486-25-9 ]
  • [ 17919-34-5 ]
  • C40H26 [ No CAS ]
  • 7
  • [ 486-25-9 ]
  • [ 525-03-1 ]
YieldReaction ConditionsOperation in experiment
70% With [pentamethylcyclopentadienyl*Ir(N-phenyl-2-pyridinecarboxamidate)Cl]; ammonium formate; In methanol; at 37℃; for 24h; General procedure: A carbonyl compound (0.5 mmol) and Ir1 (1 mol%) were added to a 1.5-dram vial equippedwith a magnetic stir bar in methanol (2.5 mL). Solid HCOONH4 (5 mmol, 10 equiv.) was addedinto the vial and the solution was stirred at 37 C for 15 h. The solvent was evaporated underreduced pressure and then aqueous HCl was added dropwise until a pH of 1-2 was obtained. Thesolution was washed with Et2O (3×5 mL), and the aqueous layer was collected. The aqueoussolution was adjusted to pH 10-12 using KOH. The product was extracted into DCM (3×5 mL)and the combined organic phase was dried over Na2SO4, filtered, and evaporated under reducedpressure to give the isolated product.
  • 8
  • [ 4805-22-5 ]
  • [ 486-25-9 ]
  • [ 1241020-90-5 ]
YieldReaction ConditionsOperation in experiment
16% Synthesis of compound 4 (scheme 3)To a mixture of 2,5-dibromothiophene (0.50 g,1.54mmol) and metal Mg (0.089 g, 3.71 mmol) was added 20 mL of freshly distilled anhydrous THF. After being stirred for 3h at 50 0C, the solution was cooled down to ambient temperature. To another flask containing 9-fluorenone (0.61g, 3.39 mmol) in 10 mL anhydrous THF solution that was cooled to 0 0C, was added the clear solution of the resulting Grignard reagent via a double needle. The mixed solution was then stirred at this temperature for 30 min before being warmed up to ambient temperature by removing the ice bath. After being stirred for another hour, a saturated SnCl2 solution in 10% hydrochloric acid (40 mL) was added dropwise. The color of the solution immediately turned to deep blue. The solution was stirred at ambient temperature for two more hours, and the deep blue precipitate was collected by suction filtration and washed with THF, water, methanol and CH2Cl2 to afford compound 4 as dark blue solid (0.125 g, 16 % yield) . The solubility of compound 4 is very poor in any solvent, and NMR spectrum was not available. MS (MALDI ) : m/ z = 4 92 . 14 ( calcd . for C34H20S2 : 4 92 . 29 ) . HOMO : - 4 . 98 eV, LUMO : - 3 . 70 eV .
  • 9
  • [ 172732-52-4 ]
  • [ 486-25-9 ]
  • [ 13234-79-2 ]
  • 10
  • [ 172732-52-4 ]
  • [ 486-25-9 ]
  • 12
  • C24H19NO3 [ No CAS ]
  • [ 486-25-9 ]
  • [ 227960-12-5 ]
YieldReaction ConditionsOperation in experiment
0.161 g; 0.158 g With oxalic acid adsorbed on silica gel; In dichloromethane; at 20℃; for 1h; N-(9H-Fluoren-9-ylidene)-4-methylaniline oxide (10) (0.285g, 1 mmol) and methylpropiolate (2d) (0.085g, 1 mmol) in acetonitrile (10 mL) was stirred at 82 oC for 4 h. Progress of the reaction was monitored by TLC. After the complete consumption of nitrone, solvent was evaporated off and the residue was redissolved in dichloromethane in the same flask. Oxalic acid (0.09g, 1mmol) adsorbed on of silica gel (1 g) was added to the same pot and the mixture was stirred at room temperaturefor 1 h. After the completion of the reaction, solvent was removed under reduced pressure. The residue obtained was chromatographed over silica gel using amixture of hexane and ethyl acetate to give fluorenone (0.161 g, 88%) followed by the indole 13 (0.158 g, 84%). The products were further purified by recrystallization from hexane-dichloromethane mixture.
  • 13
  • [ 486-25-9 ]
  • [ 171408-84-7 ]
  • 9,9'-(9,9'-spirobi[fluorene]-2,7-diyl)bis(fluoren-9-ol) [ No CAS ]
  • 14
  • [ 525-03-1 ]
  • [ 486-25-9 ]
References: [1]Journal of the American Chemical Society,2016,vol. 138,p. 13103 - 13106.
[2]Journal of the American Chemical Society,2016,vol. 138,p. 13103 - 13106.
[3]Journal of the American Chemical Society,2016,vol. 138,p. 13103 - 13106.
[4]Journal of the American Chemical Society,2016,vol. 138,p. 13103 - 13106.
[5]Journal of the American Chemical Society,2016,vol. 138,p. 13103 - 13106.
[6]Journal of the American Chemical Society,2016,vol. 138,p. 13103 - 13106.
[7]Journal of the American Chemical Society,2016,vol. 138,p. 13103 - 13106.
[8]Journal of the American Chemical Society,2016,vol. 138,p. 13103 - 13106.
[9]Journal of the American Chemical Society,2016,vol. 138,p. 13103 - 13106.
[10]Journal of the American Chemical Society,2016,vol. 138,p. 13103 - 13106.
[11]Journal of the American Chemical Society,2016,vol. 138,p. 13103 - 13106.
[12]Journal of the American Chemical Society,2016,vol. 138,p. 13103 - 13106.
[13]Journal of the American Chemical Society,2016,vol. 138,p. 13103 - 13106.
[14]Journal of the American Chemical Society,2016,vol. 138,p. 13103 - 13106.
[15]Journal of the American Chemical Society,2016,vol. 138,p. 13103 - 13106.
[16]Journal of the American Chemical Society,2016,vol. 138,p. 13103 - 13106.
[17]Journal of the American Chemical Society,2016,vol. 138,p. 13103 - 13106.
[18]Journal of the American Chemical Society,2016,vol. 138,p. 13103 - 13106.
[19]Journal of the American Chemical Society,2016,vol. 138,p. 13103 - 13106.
[20]Journal of the American Chemical Society,2016,vol. 138,p. 13103 - 13106.
[21]Journal of the American Chemical Society,2016,vol. 138,p. 13103 - 13106.
[22]Journal of the American Chemical Society,2016,vol. 138,p. 13103 - 13106.
[23]Journal of the American Chemical Society,2016,vol. 138,p. 13103 - 13106.
[24]Journal of the American Chemical Society,2016,vol. 138,p. 13103 - 13106.
[25]Journal of the American Chemical Society,2016,vol. 138,p. 13103 - 13106.
[26]Journal of the American Chemical Society,2016,vol. 138,p. 13103 - 13106.
[27]Journal of the American Chemical Society,2016,vol. 138,p. 13103 - 13106.
[28]Journal of the American Chemical Society,2016,vol. 138,p. 13103 - 13106.
[29]Journal of the American Chemical Society,2016,vol. 138,p. 13103 - 13106.
[30]Journal of the American Chemical Society,2016,vol. 138,p. 13103 - 13106.
[31]Journal of the American Chemical Society,2016,vol. 138,p. 13103 - 13106.
[32]Journal of the American Chemical Society,2016,vol. 138,p. 13103 - 13106.
[33]Journal of the American Chemical Society,2016,vol. 138,p. 13103 - 13106.
[34]Journal of the American Chemical Society,2016,vol. 138,p. 13103 - 13106.
[35]Organic Letters,2016,vol. 18,p. 5788 - 5791.
[36]RSC Advances,2017,vol. 7,p. 48848 - 48852.
  • 15
  • [ 486-25-9 ]
  • [ 902518-11-0 ]
  • spiro[fluorene-9,8'-indolo[3,2,1-de]acridine] [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% 9-(2-Bromophenyl)carbazole (12.81 g, 40 mmol)Add in a three-necked flask,Stir and dissolve with 200 mL of anhydrous tetrahydrofuran.Nitrogen protection,Cool down to -78 ° C,Then slowly add 2.5MButyl lithium solution 16mL,After stirring for half an hour,Next 9-bukenone (7.2 g, 40 mmol)The tetrahydrofuran solution was dropped into the reaction solution.After the drop, rise to room temperature,Stir the reaction for 2 hours,Quenched by adding saturated ammonium chloride solution,Add water,Concentrated organic phase,Get a yellow oil,Add this oilA mixture of 100 mL of HAc and 20 mL of HCl was stirred and refluxed for 12 hours.Cool, then add saturated brine,And extracted with dichloromethane,The organic phase is obtained.The organic phase was washed three times with water.Evaporate to remove the solvent,The residue was recrystallized from DCM/PE.The compound 3-1 (11.50 g, yield 71percent) was obtained as a white solid.
  • 16
  • [ 486-25-9 ]
  • [ 769-26-6 ]
  • 9-(mesitylethynyl)-9H-fluoren-9-ol [ No CAS ]
  • 17
  • [ 342-62-1 ]
  • [ 174899-66-2 ]
  • [ 512787-24-5 ]
  • [ 486-25-9 ]
YieldReaction ConditionsOperation in experiment
at 50℃; for 6h; General procedure: The diazonium tetrafluoroborates (10-20 mg) were dissolved in ionic liquids (0.4 mL). The solution was heated using the conditions shown in Table 1. The ionic liquids were extracted with hexane. After removal of the solvent, the residues were analyzed by NMR, and the product distributions are summarized in Table 1. Compounds 2a,22 2b,23 2c,24 2d,23 2e,22 3a,25 3d,26 3e,27 and 3f27 were identified by comparing their NMR spectra with those reported in the literature. The isomers ArOSO(CF3)(NTf) (4a-4f) and ArNTf2 (5a-5f) were attempted to be purified with SiO2 column chromatography using hexane-CH2Cl2 or hexane-ether as an eluent. However, they could not be separated by chromatography.
  • 18
  • [ 486-25-9 ]
  • [ 902518-11-0 ]
  • C31H20BrNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% <strong>[902518-11-0]N-(2-bromophenyl)carbazole</strong> (0.1605 g, 0.5 mmol), magnesium turnings (0.1200 g, 5.0 mmol), 1-3 iodine,5mL of tetrahydrofuran was added to the reaction flask in turn, stirring and heating were initiated. Then, 20 mL of a tetrahydrofuran solution of <strong>[902518-11-0]N-(2-bromophenyl)carbazole</strong> (1.6050 g, 5.0 mmol) was slowly added to the reaction flask under an ice-water bath, after the magnesium turnings were completely reacted. A 30 mL solution of 9-fluorenone (0.9000 g, 5.0 mmol) in tetrahydrofuran was slowly added dropwise to the reaction flask. After dropping,Heat at reflux for 5-48 hours. Then stop heating and slowly return to room temperature. Quench the reaction with saturated ammonium chloride solution. Extract with dichloromethane, Drying over anhydrous sodium sulfate, suction filtration, concentration, and column chromatography give 9-(2-<strong>[902518-11-0]N-(2-bromophenyl)carbazole</strong>)-9-hydroxyindole;(Yield: 59percent),
  • 19
  • [ 486-25-9 ]
  • [ 1626-24-0 ]
  • [ 20525-48-8 ]
YieldReaction ConditionsOperation in experiment
75 mmol Step1.Triphenyl germane chloro 100mmol,Dissolved in anhydrous THF, cooled to -78 degrees Celsius,Under the protection of argon, 1.5 equivalents of n-butyllithium was added and reacted for 1 h.Slowly warm to -30 C, add fluorenone, the reaction is completed in 1 h, and the reaction solution is quenched with saturated aqueous ammonium chloride solution.Extracted with EtOAc, washed, dried and dried over silicagelgel column gave 75 mmol of product 1-1.
  • 20
  • [ 486-25-9 ]
  • [ 1097884-37-1 ]
  • C31H21NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% After <strong>[1097884-37-1]4-bromo-9-phenylcarbazole</strong> (60 mmol) and 200 mL of tetrahydrofuran were added to the reaction vessel, the vessel was cooled to -78 C under a nitrogen atmosphere. Then n-butyllithium (2.5 M, 60 mmol) was slowly added dropwise to the mixture. After the mixture was stirred at -78 C for 30 minutes, it was stirred at room temperature for 3 hours and cooled to -78 C.Thereafter, an fluorenone (60 mmol) dissolved in 200 mL of tetrahydrofuran was slowly added dropwise to the mixture. After the addition, the reaction temperature was slowly raised to room temperature, and the mixture was stirred for 16 hours. Next, an aqueous ammonium chloride solution was added to the reaction solution to complete the reaction, and the reaction solution was extracted with ethyl acetate. The extracted organic layer was then dried using magnesium sulfate and the solvent was removed using a rotary evaporator. Purification of the remaining material by column chromatography to obtain compound 1-1(19.04 g, 75% mass spectrum: 423.42).
75% Add <strong>[1097884-37-1]4-bromo-9-phenylcarbazole</strong> (60 mmol) to the reaction vesselAfter cooling with 200 mL of tetrahydrofuran, the vessel was cooled to -78 C under a nitrogen atmosphere.Then n-butyllithium (2.5 M, 60 mmol) was slowly added dropwise to the mixture.After the mixture was stirred at -78 C for 30 minutes, it was stirred at room temperature for 3 hours.And cooled to -78 C. Thereafter,Dissolved in 200mL of tetrahydrofuran fluorenone (60mmol) was slowly added dropwise to the mixture. After adding,The reaction temperature was slowly raised to room temperature, and the mixture was stirred for 16 hours.Next, an aqueous ammonium chloride solution is added to the reaction solution to complete the reaction.And the reaction solution was extracted with ethyl acetate.The dried organic layer is then dried using magnesium sulfate.And the solvent was removed using a rotary evaporator.Purification of the remaining material by column chromatography to obtain compound 1-1(19.04 g, 75%, mass spectrum: 423.42).
  • 21
  • [ 486-25-9 ]
  • [ 475250-52-3 ]
  • [ 102477-91-8 ]
  • 22
  • [ 4805-22-5 ]
  • [ 486-25-9 ]
  • C34H22O2S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
50.2 g Under a N2 atmosphere, 100 mL of n-butyllithium 2.65M hexane solution was added to a mixed solution of 42.9 g of 5,5'-dibromo-2,2'-bithiophene and 200 mL of tert-butyl methyl ether cooled to -20 C. Stir at -20 C for 20 minutes.45.4 g of 9-fluorenone (B4) was added, the temperature was gradually raised to room temperature, and the mixture was stirred at room temperature for 5 hours.Water was added to stop the reaction.It was washed with water, concentrated under reduced pressure, and then hexane was added. The resulting solid was collected by filtration, washed with hexane, and dried under reduced pressure to obtain 50.2 g of a diol (B13).
 

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