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[ CAS No. 287493-15-6 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 287493-15-6
Chemical Structure| 287493-15-6
Chemical Structure| 287493-15-6
Structure of 287493-15-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 287493-15-6 ]

CAS No. :287493-15-6 MDL No. :MFCD09909863
Formula : C17H17Br Boiling Point : -
Linear Structure Formula :- InChI Key :HJXPGCTYMKCLTR-UHFFFAOYSA-N
M.W : 301.22 Pubchem ID :12123875
Synonyms :

Calculated chemistry of [ 287493-15-6 ]

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.29
Num. rotatable bonds : 2
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 81.7
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -3.74 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.36
Log Po/w (XLOGP3) : 6.2
Log Po/w (WLOGP) : 5.54
Log Po/w (MLOGP) : 5.39
Log Po/w (SILICOS-IT) : 5.89
Consensus Log Po/w : 5.27

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -5.97
Solubility : 0.000319 mg/ml ; 0.00000106 mol/l
Class : Moderately soluble
Log S (Ali) : -5.98
Solubility : 0.000312 mg/ml ; 0.00000104 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -7.6
Solubility : 0.00000758 mg/ml ; 0.0000000252 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.7

Safety of [ 287493-15-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 287493-15-6 ]

* 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.

  • Upstream synthesis route of [ 287493-15-6 ]
  • Downstream synthetic route of [ 287493-15-6 ]

[ 287493-15-6 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 1133-80-8 ]
  • [ 75-03-6 ]
  • [ 287493-15-6 ]
YieldReaction ConditionsOperation in experiment
82% With sodium hydroxide In water; toluene at 60℃; for 8 h; To a solution of 2-bromofluorene (2.5 g, 10 mmol) in toluene (40 ml) was added tetrabutylammonium bromide (0. [8] g, 2.48 mmol) as a phase transfer catalyst. A freshly prepared solution of aqueous sodium hydroxide (25 ml, 50percent w/w) was added at once to the solution. The mixture turned orange and became viscous. To this solution, [IODOETL1ANE] (2.4 ml, 30 mmol) was added. The mixture was stirred at [60 °C] for a period of 8 h. It was diluted with ethyl acetate (25 ml) and washed several portions of water. Organic layer was dried over magnesium sulfate and concentrated in vacuuo to afford the crude product liquid. The products were purified by column chromatography (silica gel, hexane as eluent, [RF=] 0.8 on thin layer chromatography) giving colorless oil [OF 2-BROMO-9,] 9-diethylfluorene (2.5 g) in a yield of 82percent. [IH] NMR [(CDCL3)] [S0.] 24 (t, J = 8 Hz, 6H), 1.94-1. 91 (m, 4H), 7.25-7. 23 (m, 3H), 7.38-7. 36 (m, 2H), 7.49-7. 46 (m, 1H), and 7.61-7. 59 (m, 1H).
Reference: [1] Journal of Organic Chemistry, 2004, vol. 69, # 3, p. 987 - 990
[2] Patent: WO2004/7426, 2004, A1, . Location in patent: Page 9
[3] Journal of Materials Chemistry, 2006, vol. 16, # 14, p. 1366 - 1378
[4] Journal of Organic Chemistry, 2008, vol. 73, # 15, p. 5683 - 5692
[5] Chemical Communications, 2002, # 17, p. 1854 - 1855
  • 2
  • [ 74-96-4 ]
  • [ 1133-80-8 ]
  • [ 287493-15-6 ]
YieldReaction ConditionsOperation in experiment
93% With tetrabutylammomium bromide; sodium hydroxide In water; dimethyl sulfoxide at 75℃; for 8 h; Inert atmosphere Under an argon atmosphere, the 5.0g2- bromofluorene was dissolved in 10mL dimethylsulfoxide (DMSO), and then was added 0.26g of tetrabutylammonium bromide (TBABr), was added 10mL freshly prepared solution of sodium hydroxide (hydrogen sodium oxide to water mass ratio of 1: 1), after mixing, was added 4.8mL dibromoethane, for 8 hours at 75 .After completion of the reaction, cooled to room temperature, extracted with ethyl acetate, separated, the organic phase was washed three times with plenty, dried over anhydrous magnesium sulfate, the organic phase was filtered, spin dry by silica gel column chromatography with petroleum ether as eluant separation, and dried to give 5.7 g of a solid, in 93percent yield.
91%
Stage #1: With potassium hydroxide In dimethyl sulfoxide at 20℃; for 0.5 h;
Stage #2: at 20℃;
The 2-bromofluorenone (300 mg, 1 . 22mmol) dissolved in 20 ml in dimethyl sulfoxide solution, then adding potassium hydroxide, rapid stirring 30 min, a solution of red ink, slowly adding after bromo-ethane, solution gradually became purple-red, thin-layer chromatography tracking to the reaction is complete. The solution obtained is extracted with ethyl acetate, the organic layer three times washing with water, saturated NaCl solution to a washing, drying by anhydrous sodium sulfate, reducing pressure and evaporating the solvent. The crude product with pure petroleum ether column, to obtain 2-bromo -9,9 the base fluorene-diethyl [...] (colorless oily, 335.5 mg, yield 91percent).
81%
Stage #1: With sodium hydroxide In water; dimethyl sulfoxide for 0.0833333 h;
Stage #2: at 20℃; for 10 h;
To a stirred solution of compound 2 (4.90 g, 20.00 mmol) in DMSO (50 mL), NaOH aqueous solution (2 mL, 50percent u/u) was added. After 5 min of stirring, bromoethane (4.80 g, 44.00 mmol) was added slowly. The reaction mixture was stirred continuously for 10 h at room temperature. Then, 100 mL ethyl acetate was added into the mixture, washed with water to remove DMSO, dried over MgSO4, filtered and the solvent was removed. The residue was purified with chromatography on silica gel (eluting with petroleum ether) to get 3 (4.86 g, 16.20 mmol) as a white solid with 81percent yield. M.p. 52-53 C; 1 H NMR (CDCl3, 400 MHz), d (ppm): 0.31 (t, 6H, J 8.0 Hz), 1.99e2.04 (m, 4H), 7.33 (s, 3H), 7.46 (d, 2H, J 4.8 Hz), 7.57 (d, 1H, J 8.0 Hz), 7.66e7.68 (m, 1H).
Reference: [1] Chemistry - An Asian Journal, 2011, vol. 6, # 7, p. 1766 - 1777
[2] Patent: CN105481901, 2016, A, . Location in patent: Paragraph 0145; 0146; 0147
[3] Bulletin of the Korean Chemical Society, 2010, vol. 31, # 7, p. 1951 - 1955
[4] Patent: CN105418515, 2016, A, . Location in patent: Paragraph 0141; 0142; 0143
[5] Journal of Materials Chemistry C, 2018, vol. 6, # 35, p. 9453 - 9464
[6] Tetrahedron, 2016, vol. 72, # 51, p. 8479 - 8485
[7] Journal of Materials Chemistry, 2008, vol. 18, # 35, p. 4183 - 4188
[8] Journal of Materials Chemistry, 2009, vol. 19, # 13, p. 1872 - 1883
[9] Journal of Organometallic Chemistry, 2016, vol. 812, p. 280 - 286
[10] Journal of Organometallic Chemistry, 2017, vol. 829, p. 92 - 100
  • 3
  • [ 2294-79-3 ]
  • [ 287493-15-6 ]
Reference: [1] Dyes and Pigments, 2010, vol. 85, # 3, p. 86 - 92
[2] Bulletin of the Korean Chemical Society, 2010, vol. 31, # 5, p. 1371 - 1374
[3] Journal of Organic Chemistry, 2013, vol. 78, # 3, p. 1014 - 1025
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