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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 : |
|
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 |
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 |
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 |
Lipinski : | 1.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
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 |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.7 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation 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). |
Yield | Reaction Conditions | Operation 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). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With sodium hydroxide;tetrabutylammomium bromide; In water; toluene; at 60℃; for 8h; | 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, 50% 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 82%. [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). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; under 760.051 Torr; for 8 - 10h;Heating / reflux; | A mixture [OF 2-BROMO-9, 9-DIETHYLFLUORENE] (2.44 g, 8.10 mmol), diphenylamine (1.43 g, 8.5 mmol), tris (dibenzylideneacetone) dipalladium (0.018 g, 0. 25 [MMOL%),] [RAC-BINAP] (0.037 g, 0.75 mmol%), and sodium t-butoxid (1.08 g, 11.34 mmol) in dry toluene (100 ml) was heated at the refluxing temperature of the solvent for [8-10] h under an atmospheric pressure of nitrogen. After cooling the reaction mixture to room temperature, it was diluted with diethylether (60 ml), washed with brine (40 [ML)] and water. Organic layer was dried over sodium sulfate and concentrated in vacuuo. The crude product was purified by column chromatography (silica gel, hexane-toluene/9: [1] as eluent, [RF =] 0.6 on thin layer chromatography using hexane-toluene/4: [1] as eluent) to give 9,9-diethyl-2-diphenylaminofluorene (3.1 g) as a white amorphous low melting solid in a yield of 98%. 1H [NMR (CDC13) 80.] 36 (t, J = 7.3 Hz, 6H), 1.99-1. 87 (m, [4H),] 7.06-6. 99 (m, 3H), 7.15- 7.12 (m, [5H),] 7.33-7. 23 [(M,] 7H), and 7.64-7. 57 (m, [2H).] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89.7% | EXAMPLE 16 2-Bromo-9,9-diethylfluorene To a solution of diethylfluorene (22.2 g., 0.1 mol.) in propylene carbonate (100 ml), N-bromosuccinimide (17.8 g., 0.1 mol.) was added at 57 C. in portions and the mixture was stirred for 30 minutes at 60 C. The mixture was diluted with 1200 ml of water and extracted with 500 ml of toluene. The toluene extract was washed 3 times with 300 ml portions of water, dried and concentrated. The crude product from 3 batches of the same size totaled 117 g. of oil. This was distilled at 2 mm. The first fraction, b.p. 90-93 C., 22.33 g. was found to be propylene carbonate. The second fraction, b. p. 155-165 C., 81.0 g. (89.7% yield) was the desired product. Mass Spec: (m/z): 300, 302 (M+). | |
89.7% | EXAMPLE XIII 2-Bromo-9,9-diethylfluorene To a solution of diethylfluorene (22.2 g., 0.1 mol.) in propylene carbonate (100 ml), N-bromosuccinimide (17.8 g., 0.1 mol.) was added at 57 C. in portions and the mixture was stirred for 30 minutes at 60 C. The mixture was diluted with 1200 ml of water and extracted with 500 ml of toluene. The toluene extract was washed 3 times with 300 ml portions of water, dried and concentrated. The crude product from 3 batches of the same size totaled 117 g. oil. This was distilled at 2 mm. The first fraction, b.p. 90-93 C., 22.33 g., was found to be propylene carbonate. The second fraction, b. p. 155-165 C., 81.0 g. (89.7% yield), was the desired compound. Mass Spec: m/z 300, 302 (M+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; n-butyllithium; In tetrahydrofuran; water; N,N-dimethyl-formamide; | EXAMPLE 17 2-(9,9-Diethyl-2-fluorenyl)-benzothiazole This compound has been prepared by three different methods: Method A: To a solution of 2-bromo-9,9-diethyl fluorene, (45.0 g., 0.15 mol), in THF (270 ml), cooled in a dry ice-acetone bath, a solution of n-butyl lithium in hexanes (105 ml, 1.6M, 0.168 mol) was added over 20 minutes and the red solution was treated with a solution of DMF (20 ml, 0.2865 mol) in THF (30 ml) after 30 minutes. The reaction mixture was removed from the cooling bath after 1.5 hours. When the temperature of the reaction mixture reached -5 C., it was treated with a mixture of conc. hydrochloric acid (15 ml) and water (60mi). The organic phase was washed with water, the aqueous phase was extracted with toluene, and the combined organic extracts were concentrated after drying to leave the crude aldehyde as a thick colorless oil, 41.95 g. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With tetrabutylammomium bromide; sodium hydroxide; In water; dimethyl sulfoxide; at 75℃; for 8h;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 93% yield. |
91% | 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 91%). | |
81% | To a stirred solution of compound 2 (4.90 g, 20.00 mmol) in DMSO (50 mL), NaOH aqueous solution (2 mL, 50% 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 81% 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). |
With sodium hydroxide; In dimethyl sulfoxide; at 20℃; | 2-Bromo-9,9-diethylfluorene was firstly prepared by the reaction of 2-bromofluorene (2.0 g, 8.160 mmol) and bromoethane(2.4 ml, 0.033 mol) in dimethyl sulfoxide solution at room temperature. After treatment with n-butyllithium (2.4 M,7.180 mmol) and trimethyl borate (2.2 ml, 0.020 mol), the brominated compound (1.97 g, 6.528 mmol) was changed into its boronic acid derivative. A mixture of 2-bromothiazole (0.58 g,3.513 mmol), the respective boronic acid (1.33 g, 5.018 mmol) and Pd(PPh3)4 (184 mg, 0.159 mmol) was refluxed in THF solution(40 ml) and 2M Na2CO3. The ligand 2-(9,9-diethyl-9H-fluoren-2-yl)thiazole L1 was obtained as a white solid (68%). Spectral data: MS (MALDI-TOF): m/z 305.44 (M+). 1H NMR (CDCl3): delta (ppm) 8.00 (s, 1H, Ar), 7.93-7.91 (m, 1H, Ar), 7.89 (d, J=4.0 Hz,1H, Ar), 7.77-7.73 (m, 2H, Ar), 7.36-7.35 (m, 3H, Ar), 7.33 (d,J=4.0 Hz, 1H, Ar), 2.16-2.04 (m, 4H, CH2), 0.33 (t, J=7.4 Hz, 6H,CH3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With nitric acid; acetic acid; for 4h;Cooling; | 3.5g of ethyl 2-bromo-9,9-fluorene was dissolved in 30mL of glacial acetic acid was slowly added dropwise 2.8mL of fuming nitric acid, cold water bath under the reaction conditions for 4 hours.After the reaction, sodium carbonate was added so that the final solution was made basic, then extracted with ethyl acetate, separated, the organic phase was washed with water three times, dried over anhydrous magnesium sulfate, filtered and the organic phase, after the spin dry using dichloromethane / petroleum ether as eluent to silica gel column chromatography, and dried to give a pale yellow solid 3.2g, 80% yield. |
67% | With nitric acid; In dichloromethane; at 20℃; for 0.166667h; | General procedure: 2-Bromo-9,9-dialkylfluorene (10.0 mmol, 1a, 1b or 1c) was dissolved in CH2Cl2 (60 mL), in the presence of a supported catalystof SiO2/H2SO4 (4.60 g) prepared according to the literature procedure.31 HNO3 (417 mL, 10.0 mmol) was added, and the heterogeneous mixture was stirred at room temperature for 10 min. The solution was then filtered, and the filtrate was washed with aqueous saturated NaHCO3 solution (10 mL) and water (10 mL). The organic layer was dried over anhydrous MgSO4 and the solvent was evaporated under reduced pressure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With 1,1'-bis-(diphenylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate; In toluene; at 80℃; for 48h;Inert atmosphere; | General procedure: A mixture of <strong>[287493-15-6]2-bromo-9,9-diethyl-9H-fluorene</strong> (3.29g, 10mmol), aniline (1.12g, 12mmol), Pd(dba)2 (0.05g, 0.20mmol), dppf (0.06g, 0.20mmol), sodium tert-butoxide (2.40g, 25mmol), and toluene (25mL) was taken in a pressure tube and heated at 80C for 48h under N2 atmosphere. After completion of the reaction, the volatiles were removed under vacuum, and the resulting solution extracted with dichloromethane (3×60mL). The combined organic extract was washed with brine solution, dried over Na2SO4, and concentrated to leave a yellow solid. Further, the crude product was purified by column chromatography on silica gel by using hexane/dichloromethane mixture (2:1 v/v) as an eluant. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In tetrahydrofuran; toluene; at 90℃;Inert atmosphere; | Compound 4-formyl phenylboronic acid (149.94 mg, 1mmol), 2-bromo -9,9 the base fluorene-diethyl [...] (276.4 mg, 0 . 91mmol), double (triphenylporphyrin phosphorus) palladium dichloride Pd (PPh3)2Cl2(31.94 mg, 0 . 046mmol), dissolved in 20 ml tetrahydrofuran mixed solvent of toluene and (Vtoluene: VTHF= 1:1) in, under the protection of nitrogen 90 C reflux reaction, thin-layer chromatography tracking to the reaction is complete. The solution obtained after the organic solvent, a revolving off, the extraction 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 using petroleum ether and ethyl acetate mixed solvent (30:1) column, to obtain 4 - (9,9 the [...] -diethyl -9H-fluoren-2-yl) benzaldehyde (strawcoloured powder, 264.4 mg, yield 89%). |
Tags: 287493-15-6 synthesis path| 287493-15-6 SDS| 287493-15-6 COA| 287493-15-6 purity| 287493-15-6 application| 287493-15-6 NMR| 287493-15-6 COA| 287493-15-6 structure
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P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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