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CAS No. : | 2327-45-9 | MDL No. : | MFCD00662902 |
Formula : | C9H9NO5 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | UAPJKEJWOPOJJY-UHFFFAOYSA-N |
M.W : | 211.17 | Pubchem ID : | 12719167 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.22 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 53.04 |
TPSA : | 81.35 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) : | -6.18 cm/s |
Log Po/w (iLOGP) : | 1.74 |
Log Po/w (XLOGP3) : | 1.98 |
Log Po/w (WLOGP) : | 1.39 |
Log Po/w (MLOGP) : | 0.61 |
Log Po/w (SILICOS-IT) : | -0.41 |
Consensus Log Po/w : | 1.06 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.43 |
Solubility : | 0.787 mg/ml ; 0.00373 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.31 |
Solubility : | 0.102 mg/ml ; 0.000485 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -1.99 |
Solubility : | 2.17 mg/ml ; 0.0103 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.15 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
87% | at 85℃; for 96 h; Inert atmosphere; Sealed tube | A pressure flask was charged with 2-nitro-4-methoxybenzoic acid (3.98 g, 0.020 mol) and methanol(10 mL). Concentrated H2SO4 (150 μl) was added dropwise. The flask was sealed and stirred at85 °C for 4 days. The mixture was cooled and concentrated to approximately half of its originalvolume. Ethyl acetate (25 mL) was added, and the mixture was washed with water (25 mL),saturated aqueous NaHCO3 solution (2 × 25 mL), brine (2 × 25 mL) and water (2 × 25 mL). Theorganic layer was dried over MgSO4, filtered, and concentrated in vacuo to give the title compoundas a yellow oil (3.57 g, 87percent); 1H NMR (300 MHz, CDCl3) δ 8.04 (d, J = 8.8 Hz, 1H, H6), 7.04 (d,J = 2.3 Hz, 1H, H3), 7.00 (dd, J = 8.8, 2.8 Hz, 1H, H4), 3.93 (s, 3H, OMe), 3.91 (s, 3H, OMe);13C {1H} NMR (75 MHz, CDCl3) δ 166.7, 163.5, 140.2, 131.4, 126.8, 115.9, 114.2, 56.4, 53.5; datain accordance with literature values.5 |
77% | With hydrogenchloride In water at 0 - 20℃; for 22 h; Heating / reflux | Fuming hydrochloric acid was passed through an ice-cooled solution of 5-methoxy-2-nitrobenzoic acid (10g, 50.7mmol) in methanol (70mL) until saturated. The reaction mixture was warmed to room temperature for 18 hours and was then heated under reflux for 4 hours. The solvent was then evaporated under reduced pressure and the residue was partitioned between ethyl acetate and sodium hydrogen carbonate solution. The organic layer was separated and washed with sodium hydrogen carbonate solution and brine, dried over magnesium sulfate, and concentrated in vacuo to give the title compound as a brown oil in 77percent yield, 8.23g. 1H NMR(CDCI3, 400MHz) No.: 3.90-3.95 (m, 6.98-7.05 (m, 8.00-8.05(m, 1 H). MS APCI+ m/z 212 [MH]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With potassium carbonate In N,N-dimethyl-formamide at 20℃; | 5-Methoxy-2-nitro-benzoic acid (3.2 g) was dissolved in N,N-dimethylformamide (60 ml). Potassium carbonate (5.61 g) and methyl iodide (5.05 ml) were added to the solution, and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the organic layer was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography with an acetone-hexane system to give methyl 5-methoxy-2-nitro-benzoate (3.38 g, yield 99percent). Methyl 5-methoxy-2-nitro-benzoate (3.38 g) was dissolved in N,N-dimethylformamide (34 ml). Triethylamine(7 ml) and 20percent palladium hydroxide (340 mg) were added to the solution, and the mixture was stirred under a hydrogen gas atmosphere at room temperature overnight. The reaction mixture was filtered and was washed with chloroform. The solvent was removed by distillation under the reduced pressure, water was added to the residue, and the organic layer was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and saturated brine, was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography with an acetone-hexane system to give methyl 2-amino-5-methoxy-benzoate (2.87 g, yield 99percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3 h; | Methyl 5-hydroxy-2-nitrobenzoate (26.45 g, 0.134 mol) was dissolved in DMF in a 1000 ml one-Methyl iodide (20.95 g, 0.148 mol) andK2CO3 (37.08 g, 0.268 mol),Reaction at room temperature 3h.The reaction was completed, the reaction solutionPour into the water that is solid precipitation, suction filtration,The filter cake was collected to obtain 28.05 g of methyl 2-nitro-5- (methoxy) benzoate in a yield of 99percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With thionyl chloride In methanol for 20 h; Reflux | 5-methoxy-2-nitrobenzoic acid (2 g, 10.14 mmol) was dissolved in MeOH (50.7mL). 50C12 (2.96 mL, 40.6 mmol) was added and the reaction mixture was heated to reflux for 20 hours. The reaction mixture was concentrated in vacuo. The cmde material was dissolved in EtOAc and washed with 1 N NaOH, then water, then brine, dried (Na2504), filtered, and concentrated in vacuo to give Intermediate 159A (1.7786 g, 8.42 mmol, 83percent) as a brown oil: ‘H NMR (400MHz, CHLOROFORM-d) 8.04 (d, J=9.0 Hz,1H), 7.07-6.99 (m, 2H), 3.94 (s, 3H), 3.92 (s, 3H); LC-MS: Method H, The compound did not ionize. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With hydrogen; triethylamine In N,N-dimethyl-formamide at 20℃; | 5-Methoxy-2-nitro-benzoic acid (3.2 g) was dissolved in N,N-dimethylformamide (60 ml). Potassium carbonate (5.61 g) and methyl iodide (5.05 ml) were added to the solution, and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the organic layer was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography with an acetone-hexane system to give methyl 5-methoxy-2-nitro-benzoate (3.38 g, yield 99percent). Methyl 5-methoxy-2-nitro-benzoate (3.38 g) was dissolved in N,N-dimethylformamide (34 ml). Triethylamine(7 ml) and 20percent palladium hydroxide (340 mg) were added to the solution, and the mixture was stirred under a hydrogen gas atmosphere at room temperature overnight. The reaction mixture was filtered and was washed with chloroform. The solvent was removed by distillation under the reduced pressure, water was added to the residue, and the organic layer was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and saturated brine, was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography with an acetone-hexane system to give methyl 2-amino-5-methoxy-benzoate (2.87 g, yield 99percent). |
99% | With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 3 h; Inert atmosphere | A mixture of compound 21 (1.01 g, 4.77 mmol), Pd/C (10percent, 50.9 mg) and methanol (15 mL) wasstirred at room temperature under an atmosphere of hydrogen for 3 h. The mixture was filteredthrough Celite® and concentrated in vacuo to give the title compound as a yellow oil (0.860 g,99percent); 1H NMR (300 MHz, CDCl3) δ 7.34 (d, J = 3.0 Hz, 1H, H3), 6.94 (dd, J = 8.9 Hz, 3.0 Hz,1H, H4), 6.63 (d, J = 8.9 Hz, 1H, H6), 5.13 (br s, 2H, NH2), 3.87 (s, 3H, OMe), 3.76 (s, 3H, OMe);13C {1H} NMR (75 MHz, CDCl3) δ 168.4, 150.7, 145.1, 123.4, 118.4, 113.2, 110.9, 56.0, 51.7; |
94% | With hydrogen In water; ethyl acetate at 20 - 25℃; for 3 h; | To an ethyl acetate (14mL) solution of methyl 5-methoxy-2-nitrobenzoate (1.60g, 7.58 mmol), 10percent palladium-carbon (containing 50percent water) (320mg) was added and stirred under a hydrogen atmosphere of 0.25MPa at 20-25°C for 3 hours. After the reaction, palladium-carbon was filtered off and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel chromatography (hexane/ethyl acetate = 10/1 - 5/1) to give methyl 2-amino-5-methoxybenzoate (1.29g, 94percent) 1H-NMR (CDCl3) δ :3.76(3H,s), 3.88(3H,s), 5.37(2H,br), 6.63(1H,d,J=8.8Hz), 6.95(1H,dd,J=8.8, 3.1Hz), 7.35(1H,d,J=3.1Hz) |
85.3% | With iron; ammonium chloride In ethanol; water for 13 h; Reflux | Methyl 2-nitro-5- (methyloxy) benzoate (27.21 g, 0.129 mol) was added to a 1000 ml single-Soluble ethanol solution (absolute ethanol: water = 1: 1),Reducing iron powder (14.40 g, 0.258 mol) andAmmonium chloride (20.68 g, 0.387 mol),Reflux 13h.The reaction was complete, suction filtration, the filtrate was extracted with ethyl acetate, combined ethyl acetate layer, with anhydrousDried over sodium sulfate,The solvent was distilled off under reduced pressure to give 19.92 g of methyl 2-amino-5- (methoxy) benzoate, yield 85.3percent. |
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