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CAS No. : | 71590-08-4 | MDL No. : | MFCD03840746 |
Formula : | C10H10O5 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PMYOJVWSJTZGDJ-UHFFFAOYSA-N |
M.W : | 210.18 | Pubchem ID : | 11020136 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.2 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 51.17 |
TPSA : | 72.83 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.3 cm/s |
Log Po/w (iLOGP) : | 1.8 |
Log Po/w (XLOGP3) : | 1.8 |
Log Po/w (WLOGP) : | 1.18 |
Log Po/w (MLOGP) : | 1.26 |
Log Po/w (SILICOS-IT) : | 1.16 |
Consensus Log Po/w : | 1.44 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -2.31 |
Solubility : | 1.03 mg/ml ; 0.00491 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.95 |
Solubility : | 0.237 mg/ml ; 0.00113 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -1.98 |
Solubility : | 2.19 mg/ml ; 0.0104 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.85 |
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 |
---|---|---|
85% | Stage #1: With sodium hydroxide; water In methanol at 80℃; Stage #2: With hydrogenchloride In water |
5-Methoxy-isophthalic acid dimethyl ester (5g, 22.3 mmol) and NaOH (0.892 g, 22.3 mmol) is mixed in 50 ml methanol and refluxed at 80 0C overnight. The reaction mixture is cooled to room temperature and solvent is removed by rotary evaporation. The solid is treated with HCl and the solid is collected by filtration, washed with water and dried under vacuum to give 5-Methoxy-isophthalic acid monomethyl ester as white solid (4.0 g, 85percent). |
75% | Stage #1: With sodium hydroxide In methanol; water at 20℃; Stage #2: With hydrogenchloride In water |
A solution of [DIMETHYL-5-HYDROXYISOPHTHALATE] (6 g, 28. 6 mmol) and potassium carbonate (9 g, 65.4 mmol) in acetone (120 [ML)] was prepared. To this, methyl iodide (4 [ML,] 63.7 mmol) was added and the reaction was left stirring overnight at room temperature. The reaction mixture was filtered and then concentrated. The residue was dissolved in ethyl acetate and washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to yield 6.4 g (quantitative) of dimethyl-5-methoxy-isophthalate as an [OFF-WHITE SOLID. LH NMR (CDC13), 6 (PPM)] : 8. 28 (s, 1H), 7.75 (s, 2H), 3.95 (s, 6H), 3.90 (s, 3H). A suspension of dimethyl-5-methoxy-isophthalate (6.4 g, 28.5 mmol) in methanol (143 mL) was treated with 1 N sodium hydroxide (25.6 mL, 25.6 mmol). The reaction was left stirring overnight at room temperature. After the solution was concentrated, the residue was dissolved in water and transferred to a separatory funnel. The aqueous layer was washed with dichloromethane (3 times) and then acidified with 1 N [HC1] to pH 2. Ethyl acetate was used to extract the precipitate, which was then washed with brine and dried over anhydrous sodium sulfate. After removal of solvent in vacuo, 4.5 g (75percent) of 5- methoxyisophthalic acid monomethyl ester was isolated as a white [SOLID. 1H] NMR (DMSO), 8 (ppm): 8.17 (m, 1H), 7.60 (m, 2H), 3.80 (s, 3H), 3.76 (s, 3H). A suspension of 5-methoxyisophthalic acid monomethyl ester [(4. 5 MG,] 21.3 mmol) in thionyl chloride (25 mL) was heated at reflux for 3 h. The excess thionyl chloride was then removed in vacuo and the intermediate acid chloride dissolved in dichloromethane (20 mL). After cooling to [0 °C] the solution was treated with 0.5 M ammonia in 1,4-dioxane (102 mL) and then allowed to warm to room temperature. After 1.5 h of stirring the solvent was removed in vacuo and the residue was triturated with water. The precipitate was collected, washed with water and dried in vacuo to afford 4.0 g (90 percent) of 5-methoxy- isophthalamic acid methyl ester as an [OFF-WHITE SOLID. 1H] NMR [(CDC13),] [8] (ppm): 8.11 (s, 1H), 7.68 (m, 2H), 3.95 (s, 3H), 3.91 (s, 3H). A suspension of 5-methoxy-isophthalamic acid methyl ester (4.0 g, 19.1 mmol) in a dichloromethane (80 mL) at [0 °C] was treated with pyridine (6.3 mL, 77.0 mmol) and then trifluoroacetic anhydride drop-wise (6.5 mL, 46 mmol). The reaction was stirred at 0 [°C] for 20 min. and then stirred overnight at room temperature. The reaction mixture was washed with water, [1.] 0 N [HC1] and brine, dried over anhydrous sodium sulfate, filtered and concentrated to afford 3.6 g (98percent) [OF 3-CYANO-5-METHOXY-BENZOIC] acid methyl ester as a white solid. A solution of 3-cyano-5-methoxy-benzoic acid methyl ester (3.4 g, 18. 7 mmol) in THF (45 mL) was treated with 0.5 N lithium hydroxide (45 mL, 22.4 mmol). The reaction was stirred at [75°C] for 2 h and then the solvent was removed in vacuo. The residue was dissolved in a small amount of water and then acidified (pH 2) by the addition of 1 N [HC1.] Ethyl acetate was used to extract the precipitate, which was then washed with brine and dried over anhydrous sodium sulfate. After removal of solvent in vacuo, 2.5 g (77percent) of 3- [CYANO-5-METHOXYBENZOIC] acid was isolated as a white [SOLID. 1H] NMR (DMSO), [8] (ppm): 7. 86 (s, [1H),] 7.71 (m, 2H), 3. 87 (s, 3H). |
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