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Chemical Structure| 2523-37-7
Chemical Structure| 2523-37-7
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Product Details of [ 2523-37-7 ]

CAS No. :2523-37-7 MDL No. :MFCD00126475
Formula : C14H12 Boiling Point : -
Linear Structure Formula :- InChI Key :ZVEJRZRAUYJYCO-UHFFFAOYSA-N
M.W : 180.25 Pubchem ID :17299
Synonyms :

Safety of [ 2523-37-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 2523-37-7 ]

* 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 [ 2523-37-7 ]

[ 2523-37-7 ] Synthesis Path-Downstream   1~24

  • 1
  • [ 1812-51-7 ]
  • [ 2523-37-7 ]
YieldReaction ConditionsOperation in experiment
With palladium on activated charcoal at 475 - 480℃;
  • 2
  • [ 2523-37-7 ]
  • [ 6311-22-4 ]
YieldReaction ConditionsOperation in experiment
54% With lithium aluminium tetrahydride; oxygen In tetrahydrofuran at 0℃; for 2.5h; Reflux;
With pyridine; benzene-trimethyl-ammonium hydroxide; oxygen
With sodium hydroxide; potassium permanganate
Stage #1: 9-methylfluorene With triethylsilane; oxygen In acetonitrile for 1h; Irradiation; Stage #2: With triphenylphosphine

  • 3
  • [ 6284-80-6 ]
  • [ 2523-37-7 ]
YieldReaction ConditionsOperation in experiment
With soda lime durch Destillation;
  • 4
  • [ 6311-22-4 ]
  • [ 2523-37-7 ]
YieldReaction ConditionsOperation in experiment
90% With triethylsilane; boron trifluoride diethyl etherate In dichloromethane at 0 - 20℃;
90% With triethylsilane; boron trifluoride diethyl etherate In dichloromethane at 0 - 20℃;
76% Stage #1: 9-methyl-9H-fluoren-9-ol In acetic acid Heating; Stage #2: With hydrogen In acetic acid at 20℃; Further stages.;
74% Stage #1: 9-methyl-9H-fluoren-9-ol With acetic acid Reflux; Stage #2: With hydrogen 7 The synthesis of 4 starts from commercially available 9-fluorenone, which is methylated using MeMgl forming 26. This compound was then converted into 9-methyl-9W-fluorene by acid catalyzed dehydration in refluxing glacial acetic acid followed by overnight reduction using Pd/C and H2 (1 atm - balloon) in a one pot procedure. 9-Methyl-9W-fluorene was obtained in a 67% yield (2 steps) starting from 20 grams of 9-fluorenone ( 111 mmol). 9-Methyl-9AY-fiuorene was subsequently used to capture gaseous C02 after deprotonation using n-BuLi in cold THF. Using excess C02 resulted in a total isolated yield of 91% of the acid precursor 27 after recrystallization . 9-Methyl-9H- fluorene was also used for the capture of [13C]-C02 applied as limiting reagent, resulting in a 73% isolated yield of *27. 27 and *27 was then transformed quantitatively into their acid chloride derivatives 4 and *4 using oxalyl chloride and a ca DMF in CH2CI2 at 30 °C.
70% With hydrogen In acetic acid for 1h; Heating;
45% With H
With hydrogen iodide; acetic acid
With acetic acid anschliessende Hydrierung an Platin;
88 % Spectr. With 4,4'-di-tert-butylbiphenyl; lithium In tetrahydrofuran for 24h; ultrasonic irradiation;
With zinc In acetic acid
With iodine; hypophosphorous acid In acetic acid
With triethylsilane; diethyl ether; boron trifluoride
Multi-step reaction with 2 steps 1: aluminium phosphate / 250 °C / im Vakuum 2: palladium black; diethyl ether / Hydrogenation
With triethylsilane; boron trifluoride diethyl etherate In dichloromethane at 0℃; for 1h;
Multi-step reaction with 2 steps 1: acetic acid / Reflux 2: palladium on carbon; hydrogen / 760.05 Torr
With triethylsilane; boron trifluoride diethyl etherate In dichloromethane at 0℃; for 1h;

Reference: [1]Konstandaras, Nicholas; Dunn, Michelle H.; Guerry, Max S.; Barnett, Christopher D.; Cole, Marcus L.; Harper, Jason B. [Organic and Biomolecular Chemistry, 2019, vol. 18, # 1, p. 66 - 75]
[2]Cole, Marcus L.; Dunn, Michelle H.; Harper, Jason B.; Konstandaras, Nicholas; Luis, Ena T. [Organic and biomolecular chemistry, 2020, vol. 18, # 10, p. 1910 - 1917]
[3]Bowen, Martina E.; Reddy Aavula, Bhasker; Mash, Eugene A. [Journal of Organic Chemistry, 2002, vol. 67, # 25, p. 9087 - 9088]
[4]Current Patent Assignee: AARHUS UNIVERSITY - WO2012/79583, 2012, A1 Location in patent: Page/Page column 77
[5]Rakus, Klaus; Verevkin, Sergej P.; Schaetzer, Juergen; Beckhaus, Hans-Dieter; Ruechardt, Christoph [Chemische Berichte, 1994, vol. 127, # 6, p. 1095 - 1104]
[6]Ziemnicka, B.; Doane, J. W. [Molecular Crystals and Liquid Crystals (1969-1991), 1987, vol. 150, p. 361 - 374]
[7]Wanscheidt; Moldavski [Chemische Berichte, 1931, vol. 64, p. 917,925][Zhurnal Obshchei Khimii, 1931, vol. 1, p. 304,324][Chemisches Zentralblatt, 1931, vol. 102, # II, p. 3208]
[8]Badger [Journal of the Chemical Society, 1941, p. 535,537]
[9]Karaman; Kohlman; Fry [Tetrahedron Letters, 1990, vol. 31, # 43, p. 6155 - 6158]
[10]Browne,S.E.; Asher,S.E.; Cornwall,E.H. [Journal of the American Chemical Society, 1984, vol. 106, p. 1432]
[11]Meyers, Cal Y.; Lutfi, Hisham G.; Varol, Pninit; Hou, Yuqing; Robinson, Paul D. [Acta Crystallographica, Section C: Crystal Structure Communications, 2000, vol. 56, # 12, p. 1468 - 1470]
[12]Vougioukalakis, Georgios C.; Orfanopoulos, Michael [Tetrahedron Letters, 2003, vol. 44, # 48, p. 8649 - 8652]
[13]Wieland; Reindel; Ferrer [Chemische Berichte, 1922, vol. 55, p. 3315]
[14]Location in patent: experimental part Vougioukalakis, Georgios C.; Roubelakis, Manolis M.; Orfanopoulos, Michael [Journal of Organic Chemistry, 2010, vol. 75, # 12, p. 4124 - 4130]
[15]Hermange, Philippe; Lindhardt, Anders T.; Taaning, Rolf H.; Bjerglund, Klaus; Lupp, Daniel; Skrydstrup, Troels [Journal of the American Chemical Society, 2011, vol. 133, # 15, p. 6061 - 6071]
[16]Malliaros, Nikitas G.; Orfanopoulos, Michael [European Journal of Organic Chemistry, 2021, vol. 2021, # 34, p. 4846 - 4850]
  • 5
  • [ 881-04-9 ]
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  • 6
  • [ 20615-64-9 ]
  • [ 74-88-4 ]
  • [ 2523-37-7 ]
  • 7
  • [ 881-04-9 ]
  • [ 74-88-4 ]
  • [ 4569-45-3 ]
  • [ 2523-37-7 ]
  • 8
  • [ 67-56-1 ]
  • [ 6311-22-4 ]
  • [ 2523-37-7 ]
  • [ 39194-34-8 ]
  • [ 4425-82-5 ]
YieldReaction ConditionsOperation in experiment
1: 6% 2: 10% 3: 55% In water Irradiation;
1: 55% 2: 6% 3: 10% In water Irradiation;
  • 9
  • [ 86-73-7 ]
  • [ 74-88-4 ]
  • [ 4569-45-3 ]
  • [ 2523-37-7 ]
  • 10
  • [ 86-73-7 ]
  • [ 74-88-4 ]
  • [ 2523-37-7 ]
YieldReaction ConditionsOperation in experiment
100% Stage #1: 9H-fluorene With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 1.5h; Stage #2: methyl iodide In tetrahydrofuran; hexane at 20℃; for 2h; Further stages.;
99% With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;
91.9% Stage #1: 9H-fluorene With lithium diisopropyl amide In tetrahydrofuran at -10℃; for 1h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran at 20℃; Inert atmosphere; 9-Methylfluorene. To fluorene (13.5 g, 81.3mmol) dissolved in THF (75 ml), the lithium diisopropylamide (LDA) (41 ml) was dropwise added at -10 oC under N2, and the mixture wasstirred for 1 h. Then, iodomethane (5 ml) was added into the reaction in oneportion. The solution was then stirred overnight at room temperature. Then, thereaction mixture was poured into water and acidified to pH = 2-3 with 1 Mhydrochloric acid. The resulting mixture was extracted with ethyl acetate. Thecombined organic phase was washed with brine and dried over anhydrous MgSO4.After filtering, the solvent was removed in vacuum and the resulting crudeproduct was purified by column chromatography (silica, hexane) to yield a whitesolid (13.45 g, 91.9 %).
91% Stage #1: 9H-fluorene With n-butyllithium In tetrahydrofuran; hexane at -60 - 20℃; for 1.75h; Inert atmosphere; Schlenk technique; Stage #2: methyl iodide In tetrahydrofuran; hexane at -60 - 20℃; for 2.33333h; Inert atmosphere; Schlenk technique;
88% With n-butyllithium In tetrahydrofuran
75% Stage #1: 9H-fluorene With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; Stage #2: methyl iodide In tetrahydrofuran; hexane at -78 - 20℃;
50% Stage #1: 9H-fluorene With n-butyllithium In tetrahydrofuran; hexane at -78℃; Stage #2: methyl iodide In tetrahydrofuran; hexane at -78 - 20℃;
With n-butyllithium 1.) hexane, THF, -78 deg C, 30 min, 2.) hexane, THF, a) -78 deg C, 30 min, b) RT, overnight; Yield given. Multistep reaction;
With n-butyllithium 1.) THF, -78 deg C, 45 min.; up to room temp., 1 h., 2.) -78 deg C, 45 min., THF,; up to room temp., 12 h.; Yield given. Multistep reaction;
Stage #1: 9H-fluorene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.166667h; Stage #2: methyl iodide In tetrahydrofuran; hexane at -78℃; for 0.25h; Further stages.;
With n-butyllithium; sodium chloride In tetrahydrofuran; hexane; ethyl acetate 5 2-(Bromoacetyl)-9-methylfluorene PREPARATION 5 2-(Bromoacetyl)-9-methylfluorene To a solution of 30 g. of fluorene in 500 ml. of anhydrous tetrahydrofuran cooled to -78° C. by means of an external dry ice/acetone bath were added 120.5 ml. of a 1.6 M solution of n-butyl lithium in hexane. After stirring for 30 minutes, the reaction mixture was added to a -78° C. solution of 56.2 ml. of methyl iodide in 60 ml. of anhydrous tetrahydrofuran. The reaction was stirred for 30 minutes at -78° C. and then overnight at room temperature. The tetrahydrofuran was removed by evaporation and the residue was dissolved in ethyl acetate. The ethyl acetate was washed with water followed by a saturated sodium chloride solution, dried over magnesium sulfate, filtered and evaporated to dryness. Recrystallization from methanol provided 26.5 g. of 9-methylfluorene, m.p. 44°-45° C.
85 %Chromat. With lithium diisopropyl amide In tetrahydrofuran at -10℃;

Reference: [1]Fleckenstein, Christoph A.; Plenio, Herbert [Chemistry - A European Journal, 2007, vol. 13, # 9, p. 2701 - 2716]
[2]Süveges, Bastian D.; Podlech, Joachim [European Journal of Organic Chemistry, 2015, vol. 2015, # 5, p. 987 - 994]
[3]Tang, Xiaoyan; Zhong, Qixuan; Xu, Ji; Li, Haiqing; Xu, Sinong; Cui, Xueyuan; Wei, Bo; Ma, Yunsheng; Yuan, Rongxin [Inorganica Chimica Acta, 2016, vol. 442, p. 195 - 199]
[4]Löffler, Julian; Gauld, Richard M.; Feichtner, Kai-Stephan; Rodstein, Ilja; Zur, Jana-Alina; Handelmann, Jens; Schwarz, Christopher; Gessner, Viktoria H. [Organometallics, 2021, vol. 40, # 16, p. 2888 - 2900]
[5]Abzhanova, Ainur; Ivanova, Lena V.; Wang, Denan; Navale, Tushar S.; Abdelwahed, Sameh H.; Ivanov, Maxim V.; Lindeman, Sergey; Rathore, Rajendra; Reid, Scott A. [Journal of Photochemistry and Photobiology A: Chemistry, 2019, vol. 374, p. 125 - 130]
[6]Zhang, Dingjun; Chen, Lei; Chen, Jianmin; Liang, Yongming; Zhou, Huidi [Synthetic Communications, 2005, vol. 35, # 20, p. 2609 - 2613]
[7]Jung, Sebastian T.; Podlech, Joachim [Journal of Organic Chemistry, 2020, vol. 85, # 16, p. 10951 - 10957]
[8]Robertson; Krushinski; Beedle; Leander; Wong; Rathbun [Journal of Medicinal Chemistry, 1986, vol. 29, # 9, p. 1577 - 1586]
[9]Brisse, Francois; Durocher, Gilles; Gauthier, Sylvain; Gravel, Denis; Marques, Rolande; et al. [Journal of the American Chemical Society, 1986, vol. 108, # 21, p. 6579 - 6586]
[10]Chebny, Vincent J.; Rathore, Rajendra [Journal of the American Chemical Society, 2007, vol. 129, # 27, p. 8458 - 8465]
[11]Current Patent Assignee: ELI LILLY & CO - US4533670, 1985, A
[12]Casarini, Daniele; Lunazzi, Lodovico; Mazzanti, Andrea [Organic and Biomolecular Chemistry, 2009, vol. 7, # 8, p. 1619 - 1626]
  • 11
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  • [ 60930-47-4 ]
  • 12
  • [ 74-83-9 ]
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  • 14
  • [ 260-94-6 ]
  • [ 6284-80-6 ]
  • [ 2523-37-7 ]
  • 9-(9H-Fluoren-9-ylmethyl)-acridine [ No CAS ]
  • 9-(9H-Fluoren-9-ylmethyl)-9,10-dihydro-acridine [ No CAS ]
  • [ 4838-42-0 ]
YieldReaction ConditionsOperation in experiment
1: 3% 2: 8% 3: 13% 4: 10% In acetonitrile for 14h; Ambient temperature; Irradiation;
  • 15
  • [ 6284-80-6 ]
  • [ 2523-37-7 ]
  • 9-(9H-Fluoren-9-ylmethyl)-acridine [ No CAS ]
  • 9-(9H-Fluoren-9-ylmethyl)-9,10-dihydro-acridine [ No CAS ]
  • [ 4838-42-0 ]
YieldReaction ConditionsOperation in experiment
1: 8% 2: 19% 3: 13% 4: 3% With acridine In acetonitrile for 14h; Ambient temperature; Irradiation;
  • 16
  • [ 219661-48-0 ]
  • [ 1127-76-0 ]
  • [ 2523-37-7 ]
  • [ 573-98-8 ]
  • [ 91-57-6 ]
  • 17
  • [ 1812-51-7 ]
  • [ 86-73-7 ]
  • [ 85-01-8 ]
  • [ 2523-37-7 ]
YieldReaction ConditionsOperation in experiment
at 475 - 480℃;
  • 18
  • [ 20615-64-9 ]
  • [ 74-88-4 ]
  • aqueous KOH [ No CAS ]
  • [ 2523-37-7 ]
  • 19
  • [ 2523-37-7 ]
  • [ 486-25-9 ]
  • [ 6311-22-4 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 9-methylfluorene With triethylsilane; [Bu4N]4W10O32; oxygen In acetonitrile at 5 - 10℃; for 1h; Irradiation; Stage #2: With triphenylphosphine Further stages.;
  • 20
  • [ 1989-32-8 ]
  • [ 2523-37-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 1.) Mg / 1.) Et2O, 2.) Et2O 2: 1.) NaH / 1.) THF, 2.) THF, 0 deg C to 25 deg C 3: 10 percent / C6H5SH / various solvent(s) / 1 h / 180 °C
  • 21
  • [ 1450-14-2 ]
  • [ 6311-22-4 ]
  • [ 2523-37-7 ]
  • [ 1403992-17-5 ]
YieldReaction ConditionsOperation in experiment
With 1% Au/TiO2 In ethyl acetate at 55℃; for 1h; Overall yield = 96 %;
  • 23
  • [ 5324-30-1 ]
  • [ 2523-37-7 ]
  • diethyl (2-(9-methyl-9H-fluoren-9-yl)ethyl)phosphonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With sodium hydride In dimethyl sulfoxide at 60℃; for 6h; Inert atmosphere; To 9-methylfluorene (3.6 g, 20 mmol) in dry DMSO (40 mL), NaH (60%, 0.48 g, 20 mmol) wasadded slowly in a N2 atmosphere. Then, diethyl (2-bromoethyl)phosphonate(5.0 g, 20.4 mmol) was addedinto the reaction, and then mixture was heated at 60 oC for 6 h. Theresulted mixture was poured into water (50 mL), which was extracted with ethylacetate (3×40 mL). The organic phase was washed with brine, and dried withmagnesium sulfate and the solvent was removed under vacuum. The residue wasdissolved in a minimum amount of ethyl acetate and chromatographic separationon silica was achieved by eluting with pet. ether:ethyl acetate (2:1). Thesolvent was removed under reduced pressure to give(2-(9-methyl-9H-fluoren-9-yl)ethyl)phosphonate as pale yellow liquid (5 g, 75%).
  • 24
  • [ 2523-37-7 ]
  • [ 6311-22-4 ]
  • [ 15300-82-0 ]
YieldReaction ConditionsOperation in experiment
1: 56% 2: 47% With lithium aluminium tetrahydride In tetrahydrofuran at 4℃; for 3h; Reflux;
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