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CAS No. : | 27060-75-9 | MDL No. : | MFCD00060687 |
Formula : | C8H9BrO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BLZNSXFQRKVFRP-UHFFFAOYSA-N |
M.W : | 201.06 | Pubchem ID : | 117915 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.25 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 45.6 |
TPSA : | 9.23 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.27 cm/s |
Log Po/w (iLOGP) : | 2.47 |
Log Po/w (XLOGP3) : | 3.18 |
Log Po/w (WLOGP) : | 2.77 |
Log Po/w (MLOGP) : | 2.88 |
Log Po/w (SILICOS-IT) : | 2.96 |
Consensus Log Po/w : | 2.85 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.47 |
Solubility : | 0.0684 mg/ml ; 0.00034 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.04 |
Solubility : | 0.181 mg/ml ; 0.000902 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.77 |
Solubility : | 0.0342 mg/ml ; 0.00017 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.18 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | 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 |
---|---|---|
78% | With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 80℃; for 18 h; | To a CCl4 solution (125 mL) of 2-bromo-5-methoxytoluene (0.050 mol) and NBS (0.055 mol) was added AIBN (0.001 mol), and the mixture was stirred at 80 °C for 18 h. The mixture was diluted with hexane before filtration through a Celite pad. Evaporation of the solvent followed by washing of the residue with ethyl acetate gave 4-bromo-3-(bromomethyl)anisole. |
72% | With N-Bromosuccinimide; dibenzoyl peroxide In dichloromethane | a 4-Bromo-3-bromomethylanisole To a stirred solution of 4-bromo-3-methylanisole (100 g, 497 mmol) in dry dichloromethane (500 mL) was added N-bromosuccinimide (97 g, 545 mmol) followed by benzoyl peroxide (6 g, 25 mmol). The reaction was gently refluxed with a 150 watt flood lamp with reflector placed approximately 12 inches from the reaction flask. After 24 h the reaction was concentrated by rotary evaporation to half its volume and allowed to sit for 4 h. The white precipitate which formed was filtered off and rinsed with a small volume of dichloromethane. The filtrate was concentrated to dryness and the remaining solid was triturated with hexanes and filtered. Drying under vacuum gave the title compound (100.25 g, 72percent) as white needles: GC tR=6.56 min (HP 530 Jm*20 m methylsilicone column, He carrier flow 20 mL/min, 100° C. initial temp., 1 min initial time, 10° C./min rate, 200° C. final temp., 1 min final time); 1H NMR (400 MHz, CDCl3) δ 7.44 (d, J=10 Hz, 1H), 6.99 (d, J=3 Hz, 1H), 6.73 (dd, 1H), 4.55 (s, 2H), 3.80 (s, 3H). |
72% | With N-Bromosuccinimide; dibenzoyl peroxide In dichloromethane | a 4-Bromo-3-bromomethylanisole To a stirred solution of 4-bromo-3-methylanisole (100 g, 497 mmol) in dry dichloromethane (500 mL) was added N-bromosuccinimide (97 g, 545 mmol) followed by benzoyl peroxide (6 g, 25 mmol). The reaction was gently refluxed with a 150 watt flood lamp with reflector placed approximately 12 inches from the reaction flask. After 24 h the reaction was concentrated by rotary evaporation to half its volume and allowed to sit for 4 h. The white precipitate which formed was filtered off and rinsed with a small volume of dichloromethane. The filtrate was concentrated to dryness and the remaining solid was triturated with hexanes and filtered. Drying under vacuum gave the title compound (100.25 g, 72percent) as white needles: GC tR=6.56 min (HP 530 μm*20 m methylsilicone column, He carrier flow 20 mL/min, 100° C. initial temp., 1 min initial time, 10° C./min rate, 200° C. final temp., 1 min final time); 1H NMR (400 MHz, CDCl3) δ 7.44 (d, J=10 Hz, 1H), 6.99 (d, J=3 Hz, 1H), 6.73 (dd, 1H), 4.55 (s, 2H), 3.80 (s, 3H). |
72% | With N-Bromosuccinimide; dibenzoyl peroxide In dichloromethane | a 4-Bromo-3-bromomethylanisole To a stirred solution of 4-bromo-3-methylanisole (100 g, 497 mmol) in dry dichloromethane (500 mL) was added N-bromosuccinimide (97 g, 545 mmol) followed by benzoyl peroxide (6 g, 25 mmol). The reaction was gently refluxed with a 150 watt flood lamp with reflector placed approximately 12 inches from the reaction flask. After 24 h the reaction was concentrated by rotary evaporation to half its volume and allowed to sit for 4 h. The white precipitate which formed was filtered off and rinsed with a small volume of dichloromethane. The filtrate was concentrated to dryness and the remaining solid was triturated with hexanes and filtered. Drying under vacuum gave the title compound (100.25 g, 72percent) as white needles: GC tR=6.56 min (HP 530 μm*20 m metbylsilicone column, He carrier flow 20 mL/min, 100° C. initial temp., 1 min initial time, 10° C./min rate, 200° C. final temp., 1 min final time); 1 H NMR (400 MHz, CDCl3) δ7.44 (d, J=10 Hz, 1 H), 6.99 (d, J=3 Hz, 1 H), 6.73 (dd, 1 H), 4.55 (s, 2 H), 3.80 (s, 3 H). |
65% | With N-Bromosuccinimide; 4-(benzoyloxy)benzoic acid In tetrachloromethane at 20℃; for 16 h; Reflux | l-Bromo-2-(bromomethyl)-4-methoxybenzeneTo a solution of 173 g (0.86 mol) of l-bromo-4-methoxy-2-methylbenzene in 850 ml of CCI4 153 g (0.86 mol) of NBS and 1.0 g of (PhCOO)2 were added at room temperature. This mixture was refluxed for 16 h, cooled to room temperature, and then filtered through glass frit (G2). The precipitate was additionally washed by 2 x 150 ml of CC14. The combined filtrate was evaporated to dryness, and the residue was triturated with 600 ml of n-hexane. The precipitate was filtered off (G3 glass frit), washed by 50 ml of n-hexane, and dried in vacuum. This procedure gave 121 g of the title product. Additional amount of the product was obtained by evaporation of a mother liquor followed by crystallization of the residue from 200 ml of n- hexane at -25°C. In total, 157 g (65percent; or 56percent overall yield for two stages) of 1- bromo-2-(bromomethyl)-4-methoxybenzene has been isolated.Anal. calc. for C8H8Br20: C, 34.32; H, 2.88. Found: C, 34.44; H, 2.95. |
56% | With N-Bromosuccinimide In tetrachloromethane; hexane | 1-Bromo-2-(bromomethyl)-4-methoxybenzene To a solution of 173 g (0.86 mol) of 1-bromo-4-methoxy-2-methylbenzene in 850 ml of CCl4 153 g (0.86 mol) of NBS and 1.0 g of (PhCOO)2 were added at room temperature. This mixture was refluxed for 16 h, cooled to room temperature, and then filtered through glass frit (G2). The precipitate was additionally washed by 2 x 150 ml of CCl4. The combined filtrate was evaporated to dryness, and the residue was triturated with 600 ml of n-hexane. The precipitate was filtered off (G3 glass frit), washed by 50 ml of n-hexane, and dried in vacuum. This procedure gave 121 g of the title product. Additional amount of the product was obtained by evaporation of a mother liquor followed by crystallization of the residue from 200 ml of n-hexane at -25°C. In total, 157 g (65percent; or 56percent overall yield for two stages) of 1-bromo-2-(bromomethyl)-4-methoxybenzene has been isolated. Anal. calc. for C8H8Br2O : C, 34.32; H, 2.88. Found: C, 34.44; H, 2.95. |
56% | With N-Bromosuccinimide In hexane | 1-Bromo-2-(bromomethyl)-4-methoxybenzene To a solution of 173 g (0.86 mol) of 1-bromo-4-methoxy-2-methylbenzene in 850 ml of CCl4 153 g (0.86 mol) of NBS and 1.0 g of (PhCOO)2 were added at room temperature. This mixture was refluxed for 16 h, cooled to room temperature, and then filtered through glass frit (G2). The precipitate was additionally washed by 2*150 ml of CCl4. The combined filtrate was evaporated to dryness, and the residue was triturated with 600 ml of n-hexane. The precipitate was filtered off (G3 glass frit), washed by 50 ml of n-hexane, and dried in vacuum. This procedure gave 121 g of the title product. Additional amount of the product was obtained by evaporation of a mother liquor followed by crystallization of the residue from 200 ml of n-hexane at -25° C. In total, 157 g (65percent; or 56percent overall yield for two stages) of 1-bromo-2-(bromomethyl)-4-methoxybenzene has been isolated. Anal. calc. for C8H8Br2O: C, 34.32; H, 2.88. Found: C, 34.44; H, 2.95. |
50% | With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 18 h; Inert atmosphere; Reflux | A dry, stir bar-equipped, 3-neck 250 mL round bottom flask was fitted with a reflux condenser and put under nitrogen. 77 1-bromo-4-methoxy-2-methylbenzene (1.39 mL, 2.011 g, 10.0 mmol, 1.00 eq), 121 CCl4 (20.0 mL, 0.50 Molar, not degassed), 122 N-bromosuccinimide (recrystallized, 2.67 g, 15.0 mmol, 1.50 eq), and 123 benzoyl peroxide (0.121 g, 0.50 mmol, 5 mol percent) were added by briefly removing a septum while under positive nitrogen pressure. The reaction was heated to reflux for 18 hours. (0187) The next day, the reaction was filtered through a silica gel plug, rinsing with 10/1 Hex/Et2O. The crude product was purified by normal phase column chromatography (5 cm diameter, 300 mL silica gel, isocratic 4/1 Hex/DCM), giving SI-3 as a fluffy, slightly off-white powder (1.404 g, 5.015 mmol, 50percent yield). (0188) 1H NMR (500 MHz, CDCl3) δ 7.45 (d, J=8.8 Hz, 1H), 6.99 (d, J=3.0 Hz, 1H), 6.74 (dd, J=8.8, 3.0 Hz, 1H), 4.56 (s, 2H), 3.80 (s, 3H). 13C NMR (126 MHz, CDCl3) δ 159.28, 137.90, 134.06, 116.67, 116.27, 114.85, 55.71, 33.61. HRMS (EI+) Calculated for C8H8OBr2: 277.89422; Found: 277.89402. |
21% | With N-Bromosuccinimide In tetrachloromethane for 7 h; Reflux | Into a 1000-mL round-bottom flask, was placed a solution of l-bromo-4-methoxy- 2-methylbenzene (20 g, 100.00 mmol, 1.00 equiv) in CCI4 (200 mL). Then NBS (19.58 g, 110.00 mmol, 1.10 equiv) and BPO (1.21 g, 5.00 mmol, 0.05 equiv) were added. The resulting solution was heated to reflux for 7 hs in an oil bath. The resulting solids were filtered out. The filtrate was concentrated under vacuum and applied onto a silica gel column with ethyl acetate/petroleum ether (1:500). This resulted in 5.9 g (21percent) of l-bromo-2-(bromomethyl)-4-methoxybenzene as a light yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61.1% | With 2,2'-azobis(isobutyronitrile) In chlorobenzene at 70℃; for 3 h; | 1-2) 2-Bromo-5-methoxybenzyl bromide azobisisobutyronitrile (0.60 g) was added to a mixture of 2-bromo-5-methoxytoluene (77.38 g, 384 mmol), 5,5-dimethy-1,3-dibromohydantoin (57.5 g, 200 mmol) and chlorobenzene (1500 ML), followed by stirring at 70°C for 2 hours.. azobisisobutyronitrile (0.60 g) was added thereto again and stirred for another 1 hour.. A 10percent aqueous sodium thiosulfate solution (500 ML) was added to the reaction mixture, and the organic layer was washed with a saturated aqueous sodium chloride solution.. The organic layer washed was dried over anhydrous magnesium sulfate and then concentrated to dryness to obtain a crude product of 2-bromo-5-methoxybenzyl bromide.. Thereto was added 100 ML of ice-cooled hexane to obtain a homogeneous slurry, which was filtered.. The residue was washed with 100 ML of ice-cooled hexane and then dried under reduced pressure to obtain 65.75 g (235 mmol, 61.1percent) of 2-bromo-5-methoxybenzyl bromide. NMR (CDCl3) δ 3.79 (s, 3H), 4.55 (s, 2H), 6.73 (dd, 1H, J = 3.0, 8.9 Hz), 6.99 (d, 1H, J = 3.0 Hz), 7.40 (d, 1H, J = 8.9 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | With bismuth (III) nitrate pentahydrate In 1,2-dichloro-ethane at 80℃; | To a suspension 151 (2.5 g, 12.5 mmoi) in DCE (20 mL) is added bismuth nitrate pentahydrate (7.28 g, 15 mmol) at room temperature. After stirring at 80 °C overnight, the mixture is cooled to room temperature, filtered, concentrated, and purified by silica gelcolumn chromatography (EA:PE 1:10) to give 152 as a light yellow solid (119 g, 39percent yield). (MS: [M+Hi 2460) |
27% | With nitric acid; acetic acid; trifluoroacetic acid In acetic acid at -5℃; for 2 h; | 136.2 1-Bromo-4-methoxy-2-methyl-5-nitro-benzene 1-Bromo-4-methoxy-2-methylbenzene obtained in step 136.1 (60 g, 298 mmol) was dissolved in acetic acid (150 ml) and TFA (150 ml). The mixture was cooled to -5° C. in an ice bath. Fuming nitric acid (14.56 ml, 328 mmol) was added slowly to the reaction. The resulting mixture was stirred at -5° C. for about 2 h. The reaction mixture was diluted with water (100 ml). The aqueous layer was extracted with ethyl acetate (3*100 mL) and washed with sat. NaCl (100 mL), sat. NaHCO3 (100 mL) and sat. NaCl (100 mL). The organic layer was dried with Na2SO4, filtered and concentrated. The resulting solid was purified with silica gel column chromatography (hexane/EtOAc=50:1). The proper fractions were collected and concentrated to give the title compound (20 g, 27percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With n-butyllithium In hexane | 4-Methoxy-2-methylphenylboronic Acid The title compound was prepared by reacting 4-bromo-3-methylanisole (10 g, 0.050 mol) with n-butyl lithium (24 mL of 2.5 M solution in hexane, 0.055 mol) followed by triisopropyl borate (57.7 mL, 47.02 g, 0.25 mol) according to method F to yield 5.7 g (69percent) of a white solid: MS (ESI) m/z 313 (2M-H2O-H)-. |
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