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CAS No. : | 33842-16-9 | MDL No. : | MFCD01546796 |
Formula : | C9H8O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KRPFJCUXHWEVMS-UHFFFAOYSA-N |
M.W : | 180.16 | Pubchem ID : | 287065 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.22 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 43.78 |
TPSA : | 44.76 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) : | -6.27 cm/s |
Log Po/w (iLOGP) : | 2.12 |
Log Po/w (XLOGP3) : | 1.59 |
Log Po/w (WLOGP) : | 1.2 |
Log Po/w (MLOGP) : | 1.07 |
Log Po/w (SILICOS-IT) : | 1.73 |
Consensus Log Po/w : | 1.54 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.17 |
Solubility : | 1.22 mg/ml ; 0.00679 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.14 |
Solubility : | 1.3 mg/ml ; 0.00723 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.23 |
Solubility : | 1.07 mg/ml ; 0.00596 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.26 |
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 |
---|---|---|
100% | Stage #1: With sodium tetrahydroborate In tetrahydrofuran at 65℃; for 0.5 h; Stage #2: With methanol In tetrahydrofuran for 4.5 h; Reflux |
6.7 g (0.037 mol) of III was dissolved in 50 ml of tetrahydrofuran, 8.6 g (0.223 mol) of sodium borohydride was added, the temperature was raised to 65 degrees Celsius, and the reaction was stirred for 30 minutes. The heating and stirring were stopped, and 8 ml of methanol was slowly added dropwise within 30 minutes. A large amount of bubbles appeared and the reaction was refluxed for 4 hours. The reaction was stopped, quenched with saturated ammonium chloride, filtered, and tetrahydrofuran was distilled off under reduced pressure. Ethyl acetate was added thereto, and the mixture was partitioned and washed with saturated brine, and dried over anhydrous sodium sulfate for 8 hours. The desiccant was removed by filtration and the solvent was evaporated under reduced pressure to give 5.6 g of white oil IV. TLC showed a single spot and was used directly in the lower reaction. The yield was close to 100percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With potassium hydroxide In methanol; water at 20℃; for 3 h; | A solution of methyl benzo[ ][1 ,3]dioxole-4-carboxylate (0.4 g, 2.22 mmol) in methanol (8.0 mL) was treated with 2.0 M aqueous KOH (2.2 mL) and the solution stirred at rt for 3 hours. The mixture was concentrated to ~3 mL volume, diluted with water (5 mL) and acidified to pH ~3 using 2.0 M HCI. The resulting precipitate was removed by filtration, washed with water then diethyl ether and dried in vacuo to give benzo[ ][1 ,3]dioxole-4-carboxylic acid as a beige solid (0.38 g, 97percent).1H NMR (400 MHz, DMSO-d6): δ = 7.28 (dd, J= 8.0, 1.2 Hz, 1H),6.97 (dd, J=8.0, 1.2 Hz, 1H),6.89 (t, J=8.0Hz, 1 H), 6.12 (s, 2H);13C NMR(100 Hz, DMSO-de) 165.5, 148.9, 148.5, 122.9, 121.6, 113.8, 112.5, 102.1. |
61% | at 50℃; for 5 h; | Compound P-2 (500 mg, 2.8 mmol) was weighed and suspended in 5 mL of water. Add 2N NaOH aqueous solution 10mL, Heat to 50°C for about 5 hours, The reaction solution is clear. Pour the reaction solution into ice water, Adjust pH to acidic with 2N dilute HCl There is a solid precipitated, Filtering, Dry powder 280mg, Yield 61percent. Used for the next reaction without purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81.2% | With caesium carbonate In N,N-dimethyl-formamide at 110℃; for 3 h; | 6.0 g (0.036 mol) of II and cesium carbonate (0.54 mol) are dissolved in 50 ml of DMF.Dibromomethane 11.5 ml (0.54 mol) was added dropwise at room temperature. After dripping, the temperature was raised to 110°C for 3 hours.The reaction was stopped after the reaction was cooled to room temperature and filtered. Add an equal volume of water and ethyl acetate to the filtrate to separate the solution.The aqueous phase is extracted twice with ethyl acetate, the organic phases are combined, washed with water, and washed with saturated brine.Anhydrous sodium sulfate was dried for 8 h. The desiccant was filtered off, the solvent was evaporated under reduced pressure, and the residue was separated by silica gel column chromatography.Elution with petroleum ether:ethyl acetate (6:1) to collect the desired components,Evaporation under reduced pressure gave a white solid of 5.2 g, yield 81.2percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | Stage #1: With potassium fluoride In N,N-dimethyl-formamide at 20℃; for 0.5 h; Stage #2: at 100℃; for 5 h; |
Methyl 2,3-dihydroxybenzoate (1.0 g, 5.95 mmol) in DMF (16 mL) was treated with KF (1 .79 g, 30.9 mmol) and stirred at ambient temperature for 30 minutes. Diiodomethane (1 .79 g, 6.7 mmol) was added and the reaction heated at 100 °C for 5 hours. The reaction mixture was cooled to rt, poured onto water (100 mL) and extracted using diethyl ether (2 x 50 mL). The combined organics were washed with water (50 mL), brine(50 mL), dried (MgS04) and concentrated in vacuo. The crude product was purified by column chromatography on silica gel using 10percent EtOAc-petroleum ether eluent to give methyl benzo[ ][1 ,3]dioxole-4- carboxylate as a white crystalline solid (0.56 g; 52percent);1H NMR (400 MHz, CDCI3): δ = 7.41 (dd, J= 8.0, 1.2 Hz, 1 H), 6.97 (dd, J= 8.0, 1 .2 Hz, 1 H), 6.86 (t, J = 8.0 Hz, 1 H), 6.1 (s, 2H), 3.93 (s, 3H). |
37% | Stage #1: With potassium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: at 60℃; for 6 h; |
Weigh compound D-1 (1 g, 6.0 mmol) in 10 mL DMF. Add anhydrous potassium carbonate (2.5 g, 17.8 mmol), The reaction was stirred at room temperature overnight. Slowly add CH2I2 (1.9 g, 7.1 mmol) after overnight Solution with 5mL DMF, After heating, the reaction is heated to about 60°C. TLC monitors the end of the reaction, After about 6 hours, the reaction is over. Pour into ice water, Extract with ethyl acetate (50 mL × 2) The organic phase was washed three times and dried over anhydrous Na2SO4. Filtering, Concentrated as a pale yellow oil, Separation with 300-400 mesh silica gel column chromatography, The eluent was n-hexane:ethyl acetate=3:1 (v/v) to obtain 396 mg of white crystals. Yield 37percent. |
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