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CAS No. : | 60547-92-4 | MDL No. : | MFCD04114356 |
Formula : | C15H13NO6 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VTHHRADLOLKTLD-UHFFFAOYSA-N |
M.W : | 303.27 | Pubchem ID : | 10859633 |
Synonyms : |
|
Num. heavy atoms : | 22 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.13 |
Num. rotatable bonds : | 6 |
Num. H-bond acceptors : | 6.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 79.69 |
TPSA : | 101.58 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -6.23 cm/s |
Log Po/w (iLOGP) : | 1.9 |
Log Po/w (XLOGP3) : | 2.71 |
Log Po/w (WLOGP) : | 2.73 |
Log Po/w (MLOGP) : | 1.51 |
Log Po/w (SILICOS-IT) : | 0.67 |
Consensus Log Po/w : | 1.9 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -3.44 |
Solubility : | 0.111 mg/ml ; 0.000367 mol/l |
Class : | Soluble |
Log S (Ali) : | -4.5 |
Solubility : | 0.00967 mg/ml ; 0.0000319 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -3.93 |
Solubility : | 0.0357 mg/ml ; 0.000118 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.71 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
88% | With potassium permanganate In acetone at 30 - 50℃; for 2 h; | The compound (20g, 69.62 mmol) obtained in <Step 1> was dissolved in acetone (200 mL), and a hot 10percent potassium permanganate solution was slowly added thereto at 30°C. The mixture was stirred at 50°C for 2 hours, and cooled to room temperature. Subsequently, the mixture was filtered through a Celite pad, and washed with acetone and a small amount of hot water. The filtrate was concentrated under reduced pressure and cooled to 0°C. Then, the concentrate was acidified into pH 4 using hydrochloric acid, and the resulting mixture was stirred for 30 min and filtered to the title compound as a solid (18.5g, 88percent). NMR(300 MHz, DMSO-d6):<5 13.58(brs, 1H), 7.70(s, 1H), 7.46-7.40(m, 6H), 7.39(s, 1H), 5.25(s, 2H), 3.92(s, 3H).MS(ESI+, m/z): 304 [M+H]+ |
79% | With potassium permanganate In water; acetone at 70℃; for 4 h; | A solution of 4-(benzyloxy)-5-methoxy-2-nitrobenzaldehyde (32) (8.0 g, 28 mmol) in acetone (300 mL) was quickly charged with a hot (70 °C) solution of potassium permanganate (16.5 g, 104 mmol) in water (150 ml). The mixture was then stirred at 70 °C for 4 h. The reaction mixture was then allowed to cool to room temperature and passed through a pad of celite, which was then washed with hot water (120 mL). A solution of sodium bisulfite in hydrochloric acid (1 M, 120 mL) was added to the filtrate, which was then extracted with dichloromethane (2 x 200 mL). The combined organic extracts were subsequently dried over sodium sulfate, filtered and concentrated to give the title compound (6.7 g, 79percent) as a yellow solid, which was used in the subsequent step without further purification. (1547) NMR (400 MHz, CDCI3) £7-55 (s, lH), 7-49"7-37 (m, 6H), 5.17 (s, 2H), 4-99 (br s, lH), 3-93 (s, 3H); C NMR (100 MHz, MeOD) £168.6, 154.1, 151.0, 142.9, 137-3, 129-7, 129.4, 129.0, 123.2, 112.5, 110.0, 72.3, 57.1; MS (ES+): m/z = 302 (M+H)+, MS (ES-): m/z = 302 (M-l)-; LCMS (Method B): tR = 3.62 min, LCMS (Method A): tR= 7.02 min |
50% | With potassium permanganate In ethyl acetate; acetone | PREPARATION 80 5-Methoxy-2-nitro-4-(phenylmethyloxy)benzoic acid A solution of 5-methoxy-2-nitro-4-(phenylmethyloxy) benzaldehyde (45.11 g, 0.157 mole) in 600 ml of acetone was prepared. To this solution was added 400 ml of 10percent potassium permanganate solution over 1 hr. The resultant mixture was stirred for 1 hr at room temperature. The reaction mixture was cooled to room temperature and filtered with Celite.(R)., acetone was removed. The resulting material was made acidic with concentrated hydrochloric acid. A yellow solid formed and was separated from aqueous solution, and air dried. The yellow solid was dissolved in ethyl acetate, and filtered through sodium sulfate to remove traces of manganese dioxide, after which 25.84 g of yellow solid was obtained. A 2 g sample was recrystallized from isopropyl alcohol. The yellow solid isolated was dried in vacuo overnight at 80° C., to give 1.85 g (50percent yield) of yellow solid, mp 188° C. (with decomposition). Analysis: Calculated for C15 H13 NO6: C, 59.41; H, 4.32; N, 4.62. Found: C, 59.27; H, 4.40; N, 4.46. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With water; triethylamine; sodium hydroxide In tetrahydrofuran at 50℃; for 5 h; | To a solution of methyl 4-(benzyloxy)-5-methoxy-2- nitrobenzoate (Harve Chem, 15 g, 47.3 mmol) in tetrahydrofuran (THF, 350 mL) was added a solution of aq. NaOH (56.7 mL, 142 mmol, 2.5M). The reaction was stirred at 50 °C for 5 h. The reaction was cooled to room temperature (RT) and then concentrated in vacuo to remove the THF. The remaining aqueous layer was acidified with aq. HC1 (6 N) to pH 2. The resulting yellow precipitate was filtered, washed with water, and dried under vacuum to give 4- (benzyloxy)-5-methoxy-2-nitrobenzoic acid (14.32 g, 100percent yield). LCMS (M+H) = 304.08; NMR (400MHz, METHANOL-d4) δ 7.60 (s, 1H), 7.53 - 7.45 (m, 2H), 7.45 - 7.31 (m, 3H), 7.29 (s, 1H), 5.23 (s, 2H), 3.98 (s, 3H). |
100% | With water; sodium hydroxide In tetrahydrofuran at 50℃; for 5 h; | To a rt solution of methyl 4-(benzyloxy)-5-methoxy-2-nitrobenzoate (15 g, 47 mmol) inTHF (350 mL) was added 2.5 M aq. NaOH (56.7 mL, 142 mmol). The reaction was stirred at 50°C for 5 h. The reaction was cooled to rt and then concentrated in vacuo to remove the THF. Theremaining aqueous layer was acidified with 6 N aq. HCl to pH 2. The resulting yellow precipitatewas filtered, washed with water, and dried under vacuum to provide S1 (14.32 g, quant.). |
92% | at 50℃; for 1 h; | 4-Benzyloxy-5-methoxy-benzoic acid methyl ester (9.1 g, 29 mmol) was dissolved in methanol (145 mL) and sodium hydroxide (6 M solution, 24 mL) was added at once. Reaction mixture was stirred for 1 h at 50 degrees and methanol was evaporated. Concentrated hydrochloric acid (12 mL) was added slowly to the residue with stirring. Formed precipitate was filtered off, washed with water and dried to afford 8.1 g of 3 (92percent yield).1H NMR (500 MHz, DMSO-d6) : 7.69 (s, 1H), 7.36-7.47 (m, 5H),7.31 (s, 1H), 5.24 (s, 2H), 3.91 (s, 3H). |
92% | at 50℃; for 1 h; | 4-benzyloxy-5-methoxy-2-nitro-benzoic acid methyl ester (9.1 g, 29 mmol) was dissolved in methanol (145 mL) and sodium hydroxide (6 M solution, 24 mL) was added at once. Reaction mixture was stirred for 1 h at 50 degrees and methanol was evaporated.Concentrated hydrochloric acid (12 mL) was added slowly to the residue with stirring.Formed precipitate was filtered off, washed with water and dried to afford 8.1 g of 3 (92percent yield). 1H NMR (500 MHz, DMSO-d6) δ: 7,69 (s, 1H), 7,36-7,47 (m, 5H),7,31 (s, 1H), 5.24 (s, 21-1), 3.91 (s, 3H). |
91% | With lithium hydroxide In methanol; water at 20℃; for 2 h; | A solution of 40 (2.3 g, 7.25 mmol) in MeOH (20 mL) was added a solution of LiOH (2.25 mL, 36.24 mmol) in water (5 mL). The reaction mixture was stirred at 20° C. for 2 h. The mixture was poured into water (50 mL), and washed with EtOAc (50 mL). The water phase was adjust pH to 3-4 with 2M HCl, and extracted with EtOAc (50 mL*3). It was washed with NaCl (25 mL), dried over Na2SO4 and concentrated in vacuo to give crude 4-(benzyloxy)-5-methoxy-2-nitrobenzoic acid 41 (2.0 g, 6.59 mmol, 91percent yield) as white solid. |
1.5 kg | With lithium hydroxide monohydrate; water In tetrahydrofuran at 20℃; for 16 h; Large scale | To a solution of compound 3 (2.50 kg, 7.93 mol) in THF (20 L) and H20 (20 L) was added LiOH H20 (332.68 g, 7.93 mol) in one portion at 20 °C to give a suspension, the reaction was stirred at this temperature for 16 h. TLC (petroleum ether: ethyl acetate = 2: 1) showed that the reaction was completed. The solvent was evaporated under vacuum to remove THF. The residue was acidified with 2N HC1 until pH = 2 to give a yellow |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With nitric acid; acetic acid In dichloromethane for 6 h; | 4-(Benzyloxy)-3-methoxybenzoic acid (63.5 g, 246.0 mmol) in the mixture of CH2CI2 (400 ml) and I lOAc (100 ml) was added HNO3 (fuming, 25.0 ml, 528.5 mmol). The mixture was stirred for 6 h, concentrated, crystallized with EtOH, dried over the oven at 40 °C with vacuum to afford the title compound (63.3 g, 85percent yield). ESI MS m/z+ 326.1 (M + Na). |
85% | With nitric acid; acetic acid In dichloromethane for 6 h; | Example 9. 4-(benzyloxy)-5-methoxy-2-nitrobenzoic acid 4-(Benzyloxy)-3-methoxybenzoic acid (63.5 g, 246.0 mmol) in the mixture of CH2C12(400 ml) and FIOAc (100 ml) was added HNO3 (fuming, 25.0 ml, 528.5 mmoi). The mixture was stirred for 6 h, concentrated, crystallized with EtOH, dried over the oven at 40 °Cwith vacuum to afford the title compound (63.3 g, 85percent yield). ESI MS mlz+ 326.1 (M +Na). |
85% | With nitric acid; acetic acid In dichloromethane for 6 h; | To a solution of compound 238 (63.5 g, 246.0 mmol) in CH2Cl2 (400 ml) and HOAc (100 ml) was added HNO3 (fuming, 25.0 ml, 528.5 mmol). The mixture was stirred for 6 h, concentrated, crystallized with EtOH, dried at 40 °C under vacuum to afford the title compound (63.3 g, 85percent yield). ESI MS m/z 326.1 ([M+Na]+). |
59% | With nitric acid In dichloromethane; acetic acid at 0 - 20℃; for 3 h; | Compound 33a (20 g, 77 mmol) was added as a thick suspension in anhydrous dichloromethane (100 mL) and was cooled to 0° C. Acetic acid (191 mL) was added, resulting in a clear solution which stirred at 0° C. until cool. Nitric acid (26 mL, 581 mmol) was added slowly dropwise through an addition funnel. The ice bath was removed and the solution continued to stir at room temperature. After 3 hours, the reaction was diluted with deionized water and extracted with dichloromethane. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and the filtrate concentrated in vacuo. The crude residue was recrystallized using ethyl acetate and hexanes. The solid was filtered and washed with hexanes to give compound 33b as a yellow fluffy solid (13.8 g, y=59percent). 1H NMR (400 Hz, CDCl3): δ 7.48-7.43 (m, 6H), 7.25 (s, 1H), 5.25 (s, 2H), 4.02 (s, 3H), MS (m/z): 326.1 (M+Na)+. See FIG. 45. |
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