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CAS No. : | 16292-95-8 | MDL No. : | MFCD11840329 |
Formula : | C7H7NO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VDQSACYMBGQMFC-UHFFFAOYSA-N |
M.W : | 169.14 | Pubchem ID : | 12900532 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.14 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 43.78 |
TPSA : | 75.28 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) : | -6.74 cm/s |
Log Po/w (iLOGP) : | 1.06 |
Log Po/w (XLOGP3) : | 0.83 |
Log Po/w (WLOGP) : | 1.31 |
Log Po/w (MLOGP) : | 0.05 |
Log Po/w (SILICOS-IT) : | -0.8 |
Consensus Log Po/w : | 0.49 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.65 |
Solubility : | 3.79 mg/ml ; 0.0224 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.99 |
Solubility : | 1.72 mg/ml ; 0.0102 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.32 |
Solubility : | 8.0 mg/ml ; 0.0473 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.94 |
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 |
---|---|---|
95% | Stage #1: With water; sodium hydroxide In dimethyl sulfoxide at 80℃; for 20 h; Stage #2: With hydrogenchloride In water; dimethyl sulfoxide at 20℃; |
To a solution of 4-fluoro-2-methoxy-1-nitrobenzene (Combi-blocks, 3.4 g, 19.9 mmol) in DMSO (40 mL) was added an aqueous solution (1N) of NaOH (40 mL, 40 mmol). The reaction mixture was heated at 80° C. for 20 h. The mixture was cooled to room temperature, and the "pH” of the solution was adjusted to 5 by aqueous HCl solution. The mixture was extracted with ethyl acetate three times. The combined organic extract was washed with water, brine, dried over MgSO4, and concentrated to give 3-methoxy-4-nitrophenol as a light yellow solid (3.2 g, 95percent). |
95% | Stage #1: With sodium hydroxide In water; dimethyl sulfoxide at 80℃; for 20 h; Stage #2: With hydrogenchloride In water; dimethyl sulfoxide |
Step a: To a solution of 4-fluoro-2-methoxy-1-nitrobenzene (Combi-blocks, 3.4 g, 19.9 mmol) in DMSO (40 mL) was added an aqueous solution (1 N) of NaOH (40 mL, 40 mmol). The reaction mixture was heated at 80° C. for 20 h. The mixture was cooled to room temperature, and the "pH" of the solution was adjusted to 5 by aqueous HCl solution. The mixture was extracted with ethyl acetate three times. The combined organic extract was washed with water, brine, dried over MgSO4, and concentrated to give 3-methoxy-4-nitrophenol as a light yellow solid (3.2 g, 95percent). |
95% | Stage #1: With sodium hydroxide In dimethyl sulfoxide at 80℃; for 20 h; Stage #2: With hydrogenchloride In dimethyl sulfoxide |
Step a: To a solution of 4-fluoro-2-methoxy-1-nitrobenzene (Combi-blocks, 3.4 g, 19.9 mmol) in DMSO (40 mL) was added an aqueous solution (1 N) of NaOH (40 mL, 40 mmol). The reaction mixture was heated at 80° C. for 20 h. The mixture was cooled to room temperature, and the "pH” of the solution was adjusted to 5 by aqueous HCl solution. The mixture was extracted with ethyl acetate three times. The combined organic extract was washed with water, brine, dried over MgSO4, and concentrated to give 3-methoxy-4-nitrophenol as a light yellow solid (3.2 g, 95percent). |
95% | With sodium hydroxide In water; dimethyl sulfoxide at 80℃; for 20 h; | To a solution of 4-fluoro-2-methoxy-1-nitrobenzene (Combi-blocks) (3.4 g, 19.9 mmol) in DMSO (40 mL) was added an aqueous solution (1N) of NaOH (40 mL, 40 mmol). The reaction mixture was heated at 80° C. for 20 h. The mixture was cooled to room temperature, and the "pH" of the solution was adjusted to 5 by aqueous HCl solution. The mixture was extracted with ethyl acetate three times. The combined organic extract was washed with water, brine, dried over MgSO4, and concentrated to give 3-methoxy-4-nitrophenol as a light yellow solid (3.2 g, 95percent). |
95% | With sodium hydroxide In water; dimethyl sulfoxide at 80℃; for 20 h; | Step 1. To a solution of 4-fluoro-2-methoxy-1-nitrobenzene (Combi-blocks, 3.4 g, 19.9mmol) in DMSO (40 mL) was added an aqueous solution (1 N) of NaOH (40 mL, 40mmol). The reaction mixture was heated at 80 oC for 20 h. The mixture was cooled toroom temperature, and the “pH” of the solution was adjusted to 5 by aqueous HClsolution. The mixture was extracted with ethyl acetate three times. The combinedorganic extract was washed with water, brine, dried over MgSO4, and concentrated togive 3-methoxy-4-nitrophenol as a light yellow solid (3.2 g, 95percent). |
90.1% | at 80℃; for 20 h; | A solution of sodium hydroxide (39 mL, 117 mmol, 3M)Was added to a solution of 4-fluoro-2-methoxy-1-nitrobenzene (10.0 g, 58.4 mmol)Of thionyl chloride(100 mL)Followed by reaction at 80 ° C for 20 hours in an oil bath.After the reaction, pH = 5 was adjusted with concentrated hydrochloric acid,Then extracted with ethyl acetate (100 mL x 3)The organic phases were combined, concentrated under reduced pressure,The residue was purified by silica gel column chromatography (petroleum ether: ethyl acetate = 10: 1) to give the title compound (9.0 g, yield 90.1percent). |
74.4% | With sodium hydroxide In dimethyl sulfoxide at 50℃; for 3 h; | (0915) 2-Methoxy-4-fluoronitrobenzene (3.4 g, 19.88 mmol) was dissolved in dimethyl sulfoxide (30 mL), and NaOH solution (1 N, 40 mL, 40 mmol) was added. The mixture was heated to 50° C., and reacted for 3 h. After the reaction, water (100 mL) was added. The mixture was extracted with ethyl acetate (50 mL×3). The organic phases were combined, and concentrated. The residue was purified by silica gel column chromatography (petroleum ether:ethyl acetate=5:1) to get the title compound (2.5 g, yield: 74.4percent). |
60% | With sodium hydroxide In dimethyl sulfoxide at 20℃; for 21 h; | To a stirred solution of 24 (0.63 g, 3.7 mmol) in DMSO (5.3 mL) was added 30percent NaOH (2.5 mL, 18.0 mmol) solution. The mixture was stirred for 21 h at room temperature, cooled to 0 °C and acidified with 6 N HCl. The mixture was pour into 5percent HCl and extracted with ether several times. The combined organic layers were washed with 5percent HCl three times, then with brine, and dried over Na2SO4. The suspension was filtered and the filtrate was concentrated in vacuo. The residue was purified by column chromatography to afford 25 as a white solid (0.37 g, 60percent). |
28% | Stage #1: With sodium hydroxide In water; dimethyl sulfoxide at 90℃; for 15 h; Stage #2: With hydrogenchloride In water; dimethyl sulfoxide at 0℃; |
To a solution of 5-fluoro-2-nitroanisole (11.0 g, 64.3 mmol) in dimethylsulfoxide (30 mL) /water (5 mL) was added sodium hydroxide (5.36 g, 129 mmol), and the mixture was stirred at 9O0C for 15 hr. The reaction solution was cooled to 00C, 6N hydrochloric acid was added to adjust to pH 7. The precipitated solid was filtered off. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90_>50/50) and recrystallized from ethyl acetate-hexane to give the title compound (3.05 g, 28percent) as a white solid.1H-NMR (DMSOd6, 300 MHz) δ 3.88 (3H, s) , 6.47 (IH, dd, J = 9.1, 2.7 Hz), 6.61 (IH, d, J = 2.7 Hz), 7.89 (IH, d, J = 9.1 Hz) , 10.90 (IH, s) . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With copper(II) nitrate trihydrate In tetrahydrofuran at 50℃; for 1 h; | General procedure: A suspension of 2-methylphenol(18.5 mmol, 1.0 eq) and Cu(NO3)2.3H2O (27.7 mmol, 1.5 eq) in THF was stirred magnetically at 60°C or reflux for several hours. Then after the solvent was removed under vacuum, the mixture was extracted with EtOAc (3×30 mL). The combined organic layers were washed with brine (5mL), dried over anhydrous MgSO4 and concentrated under vacuum. The crude residue was purified by column chromatography to afford the product (67-90percent). |
35.23% | at 0℃; for 3 h; | Concentrated nitric acid (55.83 mg, 886.09 mmol) was added to a solution of trimethoxyphenol (100 mg, 805.54mmol) in acetic acid (2 mL) and stirred at 0 °C for 3 hours. The aqueous phase was extracted with ethyl acetate (20 mL* 2). The combined organic layers were washed with NaCl solution (20 mL * 2), and then dried over sodium sulfate,filtered and evaporated, and the residue was purified by column chromatography to give compound 72A (48 mg, 35.23percent).1H NMR (400MHz, METHANOL-d4) = 10.914 (s, 1H), 7.901 - 7.887(d, 1H), 6.614-6.609 (d, 1H), 6.50- 6.48 (m, 1H),3.875 (s, 3H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | Stage #1: at 50℃; Stage #2: With hydrogenchloride In methanol; water |
A solution of 3-fluoro-4-nitrophenol (0.5 g, 3.2 mmol) in 0.5M sodium methoxide in methanol (7 mL, 3.5 mmol) was stirred at 500C for 12 h. Additional 0.5M sodium methoxide in methanol (7 mL, 3.5 mmol) was added and the reaction mixture was stirred at 500C until the reaction was complete. The reaction mixture was diluted with water (50 mL), neutralised with 2M hydrochloric acid and was extracted with ethyl acetate (3 x 50 mL). The combined organic layers were washed with brine (50 mL), dried (MgSO4) and concentrated to afford J- methoxy-4-nitrophenol as a yellow solid (0.5 g, 100percent). 1H NMR (d6-DMSO) δ 10.92 (br s, IH), 7.88 (d, IH), 6.60 (d, IH), 6.46 (dd, IH), 3.86 (s, 3H); LCMS method A, (ES+) 170, RT = 1.87 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | for 72 h; Reflux | Step 1:To a solution of 3-fluoro-4-nitrophenol (5.00 g, 31.8 mmol) in anhydrous MeOH (100 mL) was added NaOMe (10.2 g, 192 mmol). The reaction mixture was heated atreflux for 72 h, adjusted to pH 6 with 2 M citric acid, and extracted with EtOAc (2 × 500 mL). The organic layers were combined, washed with brine (50 mL), dried over MgSO4, concentrated under reduced pressure and recrystallised with EtOAc to give3-methoxy-4-nitrophenolas a brown powder (4.80 g, 88percent).1H-NMR(DMSO-d6):δ3.86 (s, 3H, CH3), 6.46 (dd, 1H,J= 9.0 & 2.2 Hz, Ph-H), 6.59 (d, 1H,J= 2.3 Hz, Ph-H), 7.89 (d, 1H,J= 9.0 Hz, Ph-H), 10.98 (s, 1H, OH). |
2.7 g | for 60 h; Reflux | To a solution of 3-fluoro-4-nitrophenol (3.0 g, 19.0 mmol) in methanol (50 mL) was addedNaOMe (3.09 g, 57.32 mmol). The reaction mass was heated at reflux for 60 h. After thereaction completion, the reaction mass was concentrated, diluted with water, acidified with dil. HC1 and extracted with DCM. The organic portion was dried over Na2504 and concentrated to afford 2.7 g of the title product.’H NMR (300 MHz, DMSO-d6): 10.90 (s, 1H), 7.89-7.86 (d, J = 9.3 Hz, 1H), 6.59 (s, 1H), 6.48-6.45 (d, J = 9.3 Hz, 1H), 3.86 (s, 3H); MS [M-Hj:168.07 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29% | With bismuth (III) nitrate pentahydrate In acetone at 0℃; for 20 h; | General procedure: To a solid mixture of phenol (1–3 equiv) and Bi(NO3)35H2O (1 equiv) or Fe(NO3)39H2O (1 equiv) was added acetone (10 ml/mmol). The resulting mixture was stirred at room temperature under air or at reflux for 2–24 hours, Tables 1 and 2. When the reaction was completed the insoluble materials were filtered off using a pad of Celite and the residue was washed by acetone (ca. 5 ml/mmol). The filtrate was treated by NaHCO3 (0.1 g/mmol) until evolution of CO2 stopped. Insoluble material was filtered off again, and the solvent was removed under vacuum in a water bath 25–35°C. The nitrated products were separated or purified using silica gel chromatography, to give pure phenolic compounds. All products were characterized by 1H NMR,13C NMR and IR and were identified by comparison of the spectral data and melting points with those reported in literature and characterized. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29% | With bismuth (III) nitrate pentahydrate In acetone at 0℃; for 20 h; | General procedure: To a solid mixture of phenol (1–3 equiv) and Bi(NO3)35H2O (1 equiv) or Fe(NO3)39H2O (1 equiv) was added acetone (10 ml/mmol). The resulting mixture was stirred at room temperature under air or at reflux for 2–24 hours, Tables 1 and 2. When the reaction was completed the insoluble materials were filtered off using a pad of Celite and the residue was washed by acetone (ca. 5 ml/mmol). The filtrate was treated by NaHCO3 (0.1 g/mmol) until evolution of CO2 stopped. Insoluble material was filtered off again, and the solvent was removed under vacuum in a water bath 25–35°C. The nitrated products were separated or purified using silica gel chromatography, to give pure phenolic compounds. All products were characterized by 1H NMR,13C NMR and IR and were identified by comparison of the spectral data and melting points with those reported in literature and characterized. |