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CAS No. : | 2675-79-8 | MDL No. : | MFCD00017169 |
Formula : | C9H11BrO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XAOOZMATJDXDQJ-UHFFFAOYSA-N |
M.W : | 247.09 | Pubchem ID : | 75885 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.33 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 53.62 |
TPSA : | 27.69 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) : | -5.95 cm/s |
Log Po/w (iLOGP) : | 2.68 |
Log Po/w (XLOGP3) : | 2.62 |
Log Po/w (WLOGP) : | 2.47 |
Log Po/w (MLOGP) : | 1.9 |
Log Po/w (SILICOS-IT) : | 2.51 |
Consensus Log Po/w : | 2.44 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.17 |
Solubility : | 0.169 mg/ml ; 0.000682 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.85 |
Solubility : | 0.348 mg/ml ; 0.00141 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.64 |
Solubility : | 0.0569 mg/ml ; 0.00023 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.05 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280 | UN#: | N/A |
Hazard Statements: | H317 | 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 |
---|---|---|
60% | With ammonium hydroxide; ethylenediaminediacetic acid; copper(II) oxide; potassium hydroxide In water at 130℃; for 12 h; Sealed tube | 261mg (1mmol) of 3,4,5-trimethoxybromobenzene, 0.35mL aqueous ammonia (25-28percent, 4.655mmol), 8mg (0.1mmol) CuO, 70mg (0.4mmol) ethylenediamine-N,N'-diacetic acid, 112mg (2mmol) KOH, 1mL H2O was added 10mL reaction tube, sealed, under the reaction conditions of 130°C for 12h. After the reaction was stopped, extraction with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was evaporated under reduced pressure, purified by silica gel column chromatography purification, 3,4,5-trimethoxy aniline 110 mg of, yield 60percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With potassium phosphate In 1,4-dioxane at 110℃; for 18 h; | A Schlenk tube was charged with aryl halide (0.67 mmol, 1.0 equiv), aryl boronate ester (0.81 mmol, 1.2 equiv), potassium phosphate or CsF (3.0 equiv), Pd catalyst (0.1 equiv), 2-(dicyclohexylphosphino)biphenyl (0.2 equiv) (co-ligand was used in the presence of Pd(OAc)2 as catalyst and CsF as base (see Table 8, entries 13-15); reaction was performed at rt) and a Teflon coated stirbar. The reaction mixture was evacuated three times for ten minutes under high vacuum and backfilled with N2. Dry dioxane was added via the T-neck and the reaction mixture was heated to 110 0C for 18 h. The reaction mixture was cooled to room <n="24"/>temperature and diluted with DCM (10 rnL). The solution was filtered and the filtrated washed with DCM (100 mL). The filtrate was concentrated and purified by silica gel chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With sodium hydroxide; dimethyl sulfate In water | Synthesis of 3,4,5-trimethoxybromobenzene 18 A mixture of 74 g (0.32 mol) of 4-bromo-2,6-dimethoxy-phenol 17 and 32 g (0.8 mol) of NaOH in 850 ml of H2O was cooled to 10° C. and 45 ml (0.48 mmol) of dimethyl sulfate was added. The mixture was refluxed for 3 h and an equal amount of dimethyl sulfate (total 0.96 mol) was then added. The mixture was refluxed for another 3 h. Upon cooling overnight, the gray product solidified and was filtered off and dissolved in 1.2 l of ether. The ether solution was filtered to remove insoluble impurity and washed sequentially with 5percent NaOH solution (200 ml), water (2*200 mL), and brine (200 mL). The ether phase was dried over Na2SO4 to give a off-white solid, which was recrystallized in hexane (300 ml) to give 62.3 g (79percent) of 18. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With boron tribromide In dichloromethane at -78℃; for 1 h; | 7.44 g (30.24 mmol) of 3,4,5-trimethoxy-1-bromobenzene and 70 mL of dry dichloromethane were placed in a four-necked flask and cooled to -78 ° C. Next, 325.0 g (99.8 mmol) of BBr was gradually added dropwise, and then the mixture was stirred for 1 hour. Further, after raising the temperature to room temperature, it was added to 200 mL of ice water to precipitate a precipitate. Next, the precipitate was filtered to obtain 6.8 g (yield quant.) Of 3,4,5-hydroxy-1-bromobenzene as a white powder. 3,4,5-Hydroxy-1-bromobenzene had an m/z of 206.01 ([M+H]+) |
97% | With boron tribromide In dichloromethane at 0 - 20℃; for 16 h; | Reagents and conditions: i. BBr3 (1.0 M in CH2C12, 10 eq.), CH2C12, 0 0C to rt, 16 hrs (97percent); |
96.4% | With boron tribromide In dichloromethane at -78 - 20℃; | The mixture of 5-bromo-1,2,3-trimethoxybenzene (XXIV) (50 g, 0.2 mol) in anhydrous DCM (500 mL) was added BBr3 (167.3 g, 0.66 mol) at −78° C. dropwise while stirring. The black reaction mixture was allowed warm to room temperature and stir overnight. The reaction mixture was poured into ice water (1000 mL), and extracted with EtOAc (2×1000 mL) The EtOAc layers were dried over anhydrous Na2SO4, and concentrated to give 5-bromobenzene-1,2,3-triol (XXV) as a pale solid. (40 g, 0.195 mol, 96.4percent yield)1H NMR (DMSO-d6, 400 MHz): δ ppm 6.40 (s, 1H), 9.28 (brs, 3H); ESIMS found C6H5BrO3 m/z 205.0 (M+H). |
54% | With boron tribromide In dichloromethane at -75 - 25℃; | To a CH2CI2 solution (40 mL) of 5-bromo-l,2,3-trimethoxybenzene (4.94 g, 20 mmol) was slowly added, at -75°C under nitrogen, a CH2CI2 solution of ΒΒ (1 M, 60 mL), and the mixture was allowed to warm to 25 °C. After overnight stirring, the reaction mixture was poured into ice/water (200 mL) and extracted with ethyl acetate. The combined organic extract was washed with water, dried over anhydrous Na2S04, and filtered off from an insoluble fraction. The filtrate was evaporated to dryness under a reduced pressure and purified using column chromatography (ethyl acetate/CH2Cl2 mixture 1:9 v/v). Yield = 2.21 g (54percent). |
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