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CAS No. : | 209256-42-8 | MDL No. : | MFCD03426203 |
Formula : | C9H8O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MKWRRGVTYBMERJ-UHFFFAOYSA-N |
M.W : | 148.16 | Pubchem ID : | 18787449 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.22 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 41.17 |
TPSA : | 26.3 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) : | -6.22 cm/s |
Log Po/w (iLOGP) : | 1.66 |
Log Po/w (XLOGP3) : | 1.39 |
Log Po/w (WLOGP) : | 1.43 |
Log Po/w (MLOGP) : | 1.05 |
Log Po/w (SILICOS-IT) : | 2.65 |
Consensus Log Po/w : | 1.64 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.97 |
Solubility : | 1.58 mg/ml ; 0.0107 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.55 |
Solubility : | 4.22 mg/ml ; 0.0285 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.62 |
Solubility : | 0.358 mg/ml ; 0.00242 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.76 |
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 |
---|---|---|
100% | With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -78℃; for 0.5 h; | C. 2,3-Dihydrobenzofuran-4-carboxaldehyde DMSO (8.10 mL, 114 mmol) was added at -78°C to a stirred solution of oxalyl chloride in CH2Cl2 (40 mL of a 2M solution). A solution of Part B 2,3-dihydrobenzofuran-4-methanol (8.53 g, 56.9 mmol) in CH2Cl2 (35 mL) was added dropwise, and the solution stirred at -78°C for 30 min. Triethylamine (33 mL, 228 mmol) was added cautiously to quench the reaction. The resulting suspension was stirred at room temperature for 30 min. and diluted with CH2Cl2 (100 mL). The organic layer was washed three times with water, and twice with brine, and then concentrated in vacuo to give 2,3-dihydrobenzofuran-4-carboxaldehyde as an oil (8.42 g, 100percent) that was used without purification. |
100% | Stage #1: With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -78℃; for 0.5 h; Stage #2: With triethylamine In dichloromethane at 20℃; for 0.5 h; |
DMSO (8.10 mL, 114 mmol) was added at -78°C to a stirred solution of oxalyl chloride in CH2Cl2 (40 mL of a 2M solution). A solution of (2,3-dihydrobenzofuran-4-yl)methanol (8.53 g, 56.9 mmol) in CH2Cl2 (35 mL) was added dropwise, and the solution stirred at -78°C for 30 min. Triethyl amine (33 mL, 228 mmol) was added cautiously to quench the reaction. The resulting suspension was stirred at room temperature for 30 min and diluted with CH2Cl2 (100 mL). The organic layer was washed three times with water, and twice with brine, and then concentrated in vacuo to an oil (8.42 g, 100percent) that was used without purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | Stage #1: With osmium(VIII) oxide In tetrahydrofuran; water at 20℃; for 0.5 h; Stage #2: With sodium periodate In tetrahydrofuran; water at 20℃; for 1 h; |
To a solution of 4-ethenyl-2,3 - dihydro-1-benzofuran (5 g, 34.20 mmol, 1.00 equiv) in tetrahydrofuran (100 mL) and water (50 mL) was added 0504 (440 mg, 1.73 mmol, 0.05 equiv). The resulting solution was stirred for 30 mm at 20 °C. Then Na104 (14.7 g, 68.69 mmol, 2.00 equiv) was added. The resulting solution was allowed to react, with stirring, for an additional 1 h at room temperature. The resulting solution was diluted with 100 mL of water. Then the resulting solution was extracted with ethyl acetate (2 x 50 mL) and the organic layers combined. The resulting mixture was washed with brine (2 x 50 mL), dried over anhydrous sodium sulfate and concentrated under vacuum to afford 5 g (99percent) of 2,3-dihydro-1-benzofuran-4-carbaldehyde as light brown oil. |
69% | Stage #1: With ozone In dichloromethane Stage #2: With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; |
Ozone was bubbled into a stirring cold solution of (3 g, 21 mmol, prepared as described in WO 9933460) in dichloromethane (50 mL). The reaction was monitored by TLC (20:1 hexane/ethyl acetate). Upon completion of the reaction the mixture was purged with nitrogen for a few minutes followed by the addition of Hunig's base (N,N-ethyldiisopropylamine, 5.44 g, 42 mmol). Stirring was continued while the reaction warmed to RT. The reaction was washed with 0.5 N HCl, water, and then brine. The organic layer was dried over MgSO4; filtered and concentrated in vacuo. The title compound (oil, 2.10 g, 69percent yield) was isolated via silica gel using 10percent ethyl acetate in hexanes. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With triethylamine In dichloromethane; dimethyl sulfoxide | C. 2,3-Dihydrobenzofuran-4-carboxaldehyde STR39 DMSO (8.10 mL, 114 mmol) was added at -78° C. to a stirred solution of oxalyl chloride in CH2 Cl2 (40 mL of a 2M solution). A solution of Part B 2,3-dihydrobenzofuran-4-methanol (8.53 g, 56.9 mmol) in CH2 Cl2 (35 mL) was added dropwise, and the solution stirred at -78° C. for 30 min. Triethylamine (33 mL, 228 mmol) was added cautiously to quench the reaction. The resulting suspension was stirred at room temperature for 30 min. and diluted with CH2 Cl2 (100 mL). The organic layer was washed three times with water, and twice with brine, and then concentrated in vacuo to give 2,3-dihydrobenzofuran-4-carboxaldehyde as an oil (8.42 g, 100percent) that was used without purification. |
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