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CAS No. : | 123297-88-1 | MDL No. : | MFCD09038098 |
Formula : | C9H6O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HLSNQZQSNWFXET-UHFFFAOYSA-N |
M.W : | 146.14 | Pubchem ID : | 14354086 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 41.6 |
TPSA : | 30.21 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) : | -5.92 cm/s |
Log Po/w (iLOGP) : | 1.61 |
Log Po/w (XLOGP3) : | 1.79 |
Log Po/w (WLOGP) : | 2.25 |
Log Po/w (MLOGP) : | 0.88 |
Log Po/w (SILICOS-IT) : | 2.56 |
Consensus Log Po/w : | 1.82 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.41 |
Solubility : | 0.564 mg/ml ; 0.00386 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.04 |
Solubility : | 1.32 mg/ml ; 0.00906 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.21 |
Solubility : | 0.0895 mg/ml ; 0.000612 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.02 |
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 |
---|---|---|
80% | A solution of 6-bromo-l-benzofuran (50 g) in tetrahydrofuran (150 ml) was slowly added to isopropylmagnesium bromide (15% in THF, 38 g) at -25 C. After complete of addition the reaction mixture was stirred for 30 min at -25 C. Dimethylformamide (21 g) was added drop wise by maintaining temperature -25C. Reaction mass was slowly warmed at room temperature. Reaction was monitored by TLC. After completion of reaction, reaction mass was quenched by solution of ammonium chloride. Reaction mass was then extracted in toluene. Separated the toluene layer and concentrated to give l-benzofuran-6- carbaldehyde compound (30 g) in 80% yield. | |
54% | H).tBuLi(0.652 mL, 1.59 M in pentane, 1.00 mmol) was added to a solutionof 176 (99.0 mg, 0.502 mmol) in Et2O (2.5 mL) at 78 C under Ar.After 5 min of stirring, DMF (0.117 mL, 1.51 mmol) was added tothe reaction. The mixture was warmed to 0 C and then stirredfor 30 min. The mixture was diluted with Et2O, washed withH2O, 1 M HCl and brine, dried over Na2SO4, filtered and concentratedin vacuo. The crude product was purified by silica gel CC(EtOAc/hexane, 5:95) to give benzofuran-6-carbaldehyde (109)(51.0 mg, 0.271 mmol, 54%) as a colorless oil: 1H-NMR (CDCl3,400 MHz) d: 6.87 (d, J = 2.2 Hz, 1H, furan-H), 7.73 (d, J = 7.6 Hz,1H, Ar-H), 7.80 (dd, J = 1.6, 7.6 Hz, 1H, Ar-H), 7.83 (d, J = 2.2 Hz,1H, furan-H), 8.02 (s, 1H, Ar-H), 10.08 (s, 1H, -CHO); spectroscopicdata were consiste |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
34% | Stage #1: 2-(3-bromophenoxy)acetaldehyde diethyl acetal In toluene for 3h; Reflux; Stage #2: N,N-dimethyl-formamide With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; | 92B; 93B Example 92B - 6-bromobenzofuran (B-192); Benzofuran-6-carbaIdehvde (B-194) To a solution of compound B-191 (50 g, 0.18 mol) in toluene (500 mL) was added polyphosphoric acid (20 g) at room temperature. The mixture was heated to reflux for 3 hours. On completion, the reaction mixture was diluted with hot water (200 mL) and extracted with dichloromethane (3 x 500 mL). The combined organic layers were washed with brine (2 x 500 mL), dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was purified by silica gel column chromatography [petroleum ether: ethyl acetate = 20: 1 ] to give a mixture of compound B-192 and compound B-193 (1 1 g, 29% yield) as yellow oil; To a mixture of compound B-192 and compound B-193 (10 g, 50 mmol) in anhydrous tetrahydrofuran (100 mL) was added n-BuLi (20 mL, 50 mmol, 2.5 M in hexhane) dropwise at -78 °C. Anhydrous N,N-dimethylformamide (8.8 g, 0.10 mol) was added slowly at - 78 °C. The mixture was stirred at -78 °C for 2 hours. On completion, the reaction was quenched with water (100 mL) at -78 °C. The reaction was filtered, and the resulting filtrate was extracted with dichloromethane (3 x 200 mL), washed with brine (2 χ 200 mL), dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography [petroleum ether: ethyl acetate = 100: 1] to give compound B-194 (2.5 g, 34% yield) as a yellow oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With dihydrogen peroxide; sodium hydroxide; In water; at 75 - 90℃; | 20 g of l-benzofuran-6-carbaldehyde was charged in solution of 16.5g of NaO in 200 ml of water. Temperature was raised to 75-90C and treated drop wise with aq. (30%, 18 g) within 2-3 hr. Reaction mass was stirred and monitored till completion of reaction. Reaction mass was acidified and filtered to get l-benzofuran-6-carboxylic acid in 70% yield. |