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CAS No. : | 128851-73-0 | MDL No. : | MFCD08669477 |
Formula : | C8H5BrO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BBXQYOQXGGJUFK-UHFFFAOYSA-N |
M.W : | 197.03 | Pubchem ID : | 15158722 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 43.91 |
TPSA : | 13.14 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) : | -5.36 cm/s |
Log Po/w (iLOGP) : | 2.27 |
Log Po/w (XLOGP3) : | 3.02 |
Log Po/w (WLOGP) : | 3.2 |
Log Po/w (MLOGP) : | 2.31 |
Log Po/w (SILICOS-IT) : | 3.12 |
Consensus Log Po/w : | 2.78 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.63 |
Solubility : | 0.0462 mg/ml ; 0.000234 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.96 |
Solubility : | 0.216 mg/ml ; 0.00109 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.14 |
Solubility : | 0.0142 mg/ml ; 0.0000719 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.58 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
91.2% | Stage #1: With n-butyllithium In tetrahydrofuran at -65 - -60℃; for 4 h; Stage #2: at -65℃; for 5 h; |
5.28 g (0.0268 mol) of 6-bromobenzofuran was added to a 250 mL three-necked flask, 80 ml of dry tetrahydrofuran was added, stirred and dissolved, then placed in a freezer to cool to -65 ° C, n-butyllithium was added dropwise (2M) 14.74mL, maintained the temperature at -60 °C during the addition process, and dropwise addition completion in 1h. After the reaction was continued for 3 hours, 2.89 g (0.0321 mol) of dimethyl carbonate was added dropwise under this reaction conditions, and the dropwise addition was completed in 1 hour, and the reaction temperature was controlled to -65 ° C. After the reaction for 4 hours, the reaction was completed. and the reaction was quenched by dropwise addition of a saturated ammonium chloride solution under a low temperature condition. The reaction was quenched by dropwise addition of a saturated ammonium chloride solution under a low temperature condition, after the solvent was evaporated under reduced pressure, residue was stirred by adding 100ml of water and 100 ml of dichloromethane , and then the layers were separated. The organic layer was washed twice with saturated brine, 100 mL each time, and the dichloromethane layer was dried over anhydrous magnesium sulfate and filtered, dichloromethane was evaporated under reduced pressure to obtain 6-methyl formate benzofuran 4.3g. yield 91.2percent and HPLC purity 97.2percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | With polyphosphoric acid (PPA) In toluene at 20℃; for 4 h; Inert atmosphere; Reflux | Polyphosphoric acid (PPA) (0.743 g, 6.83 mmol) was added to asolution of 175 (0.656 g, 2.28 mmol) in toluene (4.6 mL) at roomtemperature under Ar. The mixture was headed until reflux began,this being maintained for 4 h, then cooled to room temperature,quenched with cooled H2O and extracted with EtOAc. The organiclayers were washed with brine, dried (MgSO4), filtered and concentratedin vacuo. The crude product was purified by silica gel CC(EtOAc/hexane, 2:98) to give 6-bromobenzofuran (176) (major,0.206 g, 1.05 mmol, 46percent) and 4-bromobenzofuran (177) (minor,0.183 g, 0.935 mmol, 41percent) as colorless oils: 176: 1H-NMR (CDCl3,400 MHz) d: 1H-NMR (CDCl3, 400 MHz) d: 6.75 (d, J = 1.6 Hz, 1H,furan-H), 7.36 (dd, J = 1.2, 8.4 Hz, 1H, Ar–H), 7.46 (d, J = 8.4 Hz,1H, Ar–H), 7.60 (d, J = 1.6 Hz, 1H, furan-H), 7.69 (s, 1H, Ar–H);177: 1H-NMR (CDCl3, 400 MHz) d: 6.82 (d, J = 2.4 Hz, 1H, furan-H), 7.17 (dd, J = 7.6, 8.4 Hz, Ar–H), 7.40 (d, J = 7.6 Hz, 1H, Ar–H),7.45 (d, J = 8.4 Hz, 1H, Ar–H), 7.66 (d, J = 2.4 Hz, 1H, furan-H). |
15% | With polyphosphoric acid In chlorobenzene at 80℃; for 2 h; | A mixture of 17 gm (57.8 mMol) 2-(3-bromophenoxy)acetaldehyde diethyl acetal and 17.5 gm polyphosphoric acid in 400 mL chlorobenzene was heated to 80° C. for 2 hours. The reaction mixture was cooled to room temperature and the chlorobenzene was decanted from the polyphosphoric acid. The polyphosphoric acid was washed with two 150 mL portions of diethyl ether. All or the organic phases were combined and concentrated under reduced pressure. The residue was redissolved in diethyl ether and the organic phases were washed with saturated aqueous sodium bicarbonate, water, and saturated aqueous sodium chloride, dried over magnesium sulfate and concentrated under reduced pressure. The residual oil was subjected to silica gel chromatography, eluting with hexane.Fractions containing the faster eluting isomer were combined and concentrated under reduced pressure to provide 1.7 gm (15percent) 4-bromobenzofuran.EA: Calculated for C8H5BrO: Theory: C, 48.77; H, 2.56. Found: C, 48.89; H, 2.72.Fractions containing the slower eluting isomer were combined and concentrated under reduced pressure to provide 2.5 gm (22percent) 6-bromobenzofuran.EA: Calculated for C8H5BrO: Theory: C, 48.77; H, 2.56. Found: C, 48.89; H, 2.67. |
15% | With PPA In chlorobenzene at 80℃; for 2 h; | A mixture of 17 gm (57.8 mMol) 2-(3-bromophenoxy)acetaldehyde diethyl acetal and 17.5 gm polyphosphoric acid in 400 mL chlorobenzene was heated to 80°C for 2 hours. The reaction mixture was cooled to room temperature and the chlorobenzene was decanted from the polyphosphoric acid. The polyphosphoric acid was washed with two 150 mL portions of diethyl ether. All or the organic phases were combined and concentrated under reduced pressure. The residue was redissolved in diethyl ether and the organic phases were washed with saturated aqueous sodium bicarbonate, water, and saturated aqueous sodium chloride, dried over magnesium sulfate and concentrated under reduced pressure. The residual oil was subjected to silica gel chromatography, eluting with hexane. Fractions containing the faster eluting isomer were combined and concentrated under reduced pressure to provide 1.7 gm (15percent) 4-bromobenzofuran. EA: Calculated for C8H5BrO: Theory: C, 48.77; H, 2.56. Found: C, 48.89; H, 2.72. Fractions containing the slower eluting isomer were combined and concentrated under reduced pressure to provide 2.5 gm (22percent) 6-bromobenzofuran. EA: Calculated for C8H5BrO: Theory: C, 48.77; H, 2.56. Found: C, 48.89; H, 2.67. |