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CAS No. : | 7463-51-6 | MDL No. : | MFCD00002315 |
Formula : | C8H9BrO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WMUWDPLTTLJNPE-UHFFFAOYSA-N |
M.W : | 201.06 | Pubchem ID : | 81970 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.25 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 46.1 |
TPSA : | 20.23 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) : | -5.16 cm/s |
Log Po/w (iLOGP) : | 2.04 |
Log Po/w (XLOGP3) : | 3.33 |
Log Po/w (WLOGP) : | 2.77 |
Log Po/w (MLOGP) : | 2.88 |
Log Po/w (SILICOS-IT) : | 2.94 |
Consensus Log Po/w : | 2.79 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.63 |
Solubility : | 0.0473 mg/ml ; 0.000235 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.43 |
Solubility : | 0.0744 mg/ml ; 0.00037 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.45 |
Solubility : | 0.0707 mg/ml ; 0.000352 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.09 |
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 |
---|---|---|
90% | With 1,2-ethanediylbis(triphenylphosphonium) ditribromide In methanol; dichloromethane at 20℃; for 0.0833333 h; | General procedure: To a mixture of anilines or phenols (0.7 mmol) the brominatingagent (1) (0.72 g, 0.7 mmol) in dichloromethane(30 ml)-methanol (15 ml) was added. The reactionmixture was stirred at room temperature until decolorizationof the orange solution took place. The progress of thereaction was monitored by TLC (eluent: n-hexane/ethylacetate, 7:3). After completion of the reaction, the solventwas evaporated and diethyl ether (10 ml) was added to theresidue. The supernatant was decanted and the insolubleresidue was washed by ether (3 × 10 ml). The combinedether extracts were dried on magnesium sulfate and also evaporated under vacuum to afford monobromo anilines ormonobromo phenols which was purified by flash columnchromatography over silica gel (n-hexane/ethyl acetate,7:3). |
83% | With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione In 1,2,5-thiadiazole at 20℃; | A 20.9 mg (0.171 mmol) of "compound 24" was dissolved in 210 μl of 1,2,5-thiadiazole, to which 29.3 mg (0.102 mmol) of 1,3-dibromo 5,5-dimethylhydantoin was added at room temperature under nitrogen atmosphere. On completion of reaction, 200 μl of water was added to the system, which was then subjected to separation operation. The system was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1), to give 28.5 mg (83percent yield) of "compound 25" in the form of a while solid. |
83% | With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione In dichloromethane at 20℃; | The same reaction as in Example 7 was elicited except that the solvent was changed to dichloromethane, and compound 25 was produced at an yield of 83percent. |
20% | With bromine In chloroform at 20℃; for 1 h; | 3,5-dimethylphenol (2.44g, 20.0mmol) was dissolved in 20mL of chloroform, bromine (1.0mL, 21.0mmol) was dissolved in 10mL of chloroform was slowly added dropwise to the solution at room temperature the reaction 1h. Washed with sodium thiosulfate solution, washed with water to separate the organic phase was chromatographed on silica gel, petroleum ether / ethyl acetate to give a white solid 800mg, yield 20.0percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With potassium carbonate In acetone for 12 h; Reflux | Starting fragments 1 and 2 were determined to be the key building blocks to introduce the required amino substitution in the final molecules. Fragment 1 was prepared from commercially available 4-bromo-3,5-dimethylphenol (6). The phenolic group of 6 was alkylated with iodomethane and the resulting methyl ether was then oxidized. Carboxylic acid 8 was converted to methyl ester 9. Reduction of 9 with LiBH4 (lithium borohydride), followed by treatment with NBS (/V-bromosuccinimide) and then NaCN (sodium cyanide) produced fragment 1 in good yield (Scheme 2). Reagents and conditions: (a) CH3I, K2C03, acetone, reflux, 12 h, quantitative; (b) KMn04, t- BuOH:H20, 100 °C, 18 h, 68percent; (c) MeOH, H2S04, room temp, 12 h, 85percent; (d) LiBH4, THF, room temp, 12 h, 95percent; (e) NBS, PPh3, THF, room temp, 12 h, 85percent; (f) NaCN, Kl, 18- crown-6 ether, CH3CN:H20, room temp, 24 h, 68percent. |
99% | Stage #1: With sodium hydride In tetrahydrofuran at 0 - 20℃; for 0.5 h; Stage #2: at 60℃; for 3 h; |
weighed 4-bromo-3,5-dimethylbenzene acid (1.05g, 5mmol) was dissolved in 25ml tetrahydrofuran in an ice water bath and cool to 0° C, the reaction system was added in divided portions NaH (240mg, 6mmol), naturally to room temperature, stirring was continued for 0.5 hours, then was added methyl iodide (0. 4mL, 6mmol), the reaction was stirred at 60 ° C in an oil bath for 3 hours, until the starting material the reaction was complete. 50mL50mL3 1 percent/4a (1.06g) 99percent 50mL water was added carefully to quench the reaction, 50mL per total extracted three times with ethyl acetate, the combined organic phase was washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to give the crude product was purified by flash chromatography (1percent acetic acid acetate / petroleum ether) to give the product 4a (1.06g), yield 99percent. |
97% | With potassium carbonate In DMF (N,N-dimethyl-formamide) at 20℃; for 2 h; | A mixture of commercially available 4-bromo-3,5-dimethylphenol (a compound of Formula 4) (25.0 g, 124.3 mmol), methyl iodide (35.3 g, 248.6 mmol), and potassium carbonate (34.4 g, 248.6 mmol) in 62.5 mL of DMF was stirred for 2 hours at room temperature. The reaction mixture was diluted with 300 mL of ether and washed with 250 mL of water and 5x100 mL of brine. The organic portion was dried (MgSO4), filtered, and evaporated to give an oil, which was purified by flash column chromatography (silica gel, 90:10 hexane/ethylacetate) to give 4-bromo-3,5-dimethylanisole (a compound of Formula 5) (26 g, 120.8 mmol, 97percent);1HNMR (CDCl3) δ 2.39 (s, 6H), 3.76 (s, 3H), 6.67 (s, 2H). |
94% | Stage #1: at 40℃; for 3 h; |
A solution of 4-bromo-3,5-dimethylphenol (1.00 g, 4.97 mmol) in acetone (40 mL) was treated with solid CsCO3 (1.17 g, 4.97 mmol) and methyl iodide (0. 310 mL, 4.97 mmol) and heated to 40 oC for 3 h. Additional methyl iodide (0.310 mL, 4.97 mmol) was added over the course of the reaction to replace that lost to evaporation. The acetone was removed in vacuo. The resulting white solid residue was partitioned between water and CH2CL2. The layers were separated and the aqueous layer was further extracted with CH2C12 (2 x 25 mL). The combined organic layers were washed with water (1 x 25 mL) and dried over MGS04. The solvent was removed in vacuo to afford the product 2-bromo-5-methoxy-1, 3-dimethyl-benzene (1.01 g, 94percent) as a colorless oil, which slowly solidified upon STANDING. 1H NMR (CDC13) : δ 6.644 (s, 2H), 3.762 (s, 3H), 2. 382 (s, 6H). |
65% | With potassium carbonate In N,N-dimethyl-formamide | Example 1.3.1 A mixture of 4-bromo-3,5-dimethylphenol (4.0 g, 19.9 mmol) and K2CO3 (4.14 g, 30.0 mmol) was stirred in DMF (15 mL) for 10 minutes. Iodomethane (5.76 g, 40.0 mmol) was added and the reaction mixture was heated at 35° C. for 23 hours under argon. After cooling, mixture was poured into DCM (150 mL); white solids were filtered off. The filtrate was purified by flash column (silica; 100percent hexane) to give 2.79 g of product 9 (65percent yield). |
99% | With potassium carbonate In acetone | Example 1 Synthesis of 2-bromo-5-methoxy-1,3-dimethyl-benzene. To a mixture of 4-bromo-3,5-dimethyl-phenol (40.2 g, 0.200 mol) and potassium carbonate (55.2 g, 0.400 mol) in acetone (200 mL) was added methyl iodide (24.9 mL, 0.600 mol) at room temperature under N2. The reaction mixture was then refluxed at 65° C. for 8 h. After cooling to room temperature, the mixture was filtered, and the filtrate was concentrated in vacuo. The resulting clear liquid was distilled under reduced pressure (70° C./0.1 Torr) to give 42.4 g (99percent) of title compound as a colorless liquid. 1H NMR (400 MHz, CDCl3): δ 6.663 (s, 2H), 3.778 (s, 3H), 2.402 (s, 6H); 13C NMR (100 MHz, CDCl3): δ 158.165, 139.203, 118.357, 113.953, 55.520, 24.319. MS (EI): m/z 214 [M+, 79Br 100], 216 [M+, 79Br, 96]. |
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