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CAS No. : | 385-01-3 | MDL No. : | MFCD07368753 |
Formula : | C6H4FNO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GAWNBKUTBVLIPL-UHFFFAOYSA-N |
M.W : | 157.10 | Pubchem ID : | 2782777 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 37.25 |
TPSA : | 66.05 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.22 cm/s |
Log Po/w (iLOGP) : | 1.23 |
Log Po/w (XLOGP3) : | 1.46 |
Log Po/w (WLOGP) : | 1.86 |
Log Po/w (MLOGP) : | 0.7 |
Log Po/w (SILICOS-IT) : | -0.35 |
Consensus Log Po/w : | 0.98 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.07 |
Solubility : | 1.33 mg/ml ; 0.00848 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.45 |
Solubility : | 0.553 mg/ml ; 0.00352 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -1.47 |
Solubility : | 5.34 mg/ml ; 0.034 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.64 |
Signal Word: | Danger | Class: | 9 |
Precautionary Statements: | P261-P264-P270-P272-P273-P280-P301+P312+P330-P302+P352-P305+P351+P338+P310-P333+P313-P391-P501 | UN#: | 3077 |
Hazard Statements: | H302-H315-H317-H318-H410 | Packing Group: | Ⅲ |
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 |
---|---|---|
61% | With potassium <i>tert</i>-butylate In dimethyl sulfoxide at 20℃; for 18.5 h; | A solution of potassium TERT-BUTOXIDE (1.23 g, 11 mmol) in 25 mL of anhydrous DMSO was stirred at room temperature for 30 minutes and treated with 1, 3-difluoro-2-nitrobenzene (1.59 g, 10 mmol). After 18 hours, the mixture was diluted with 150 mL of 1 N aqueous sulfuric acid and extracted with three 50 mL portions of diethyl ether. The combined organic layers were washed with water, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was dissolved in 50 mL of trifluoroacetic acid. After 30 minutes at room temperature, the mixture was concentrated in vacuo, treated with 50 mL of 1 N aqueous sodium hydroxide, and extracted with three 30 mL portions of diethyl ether. The aqueous layer was acidified with 1 N aqueous sulfuric acid and extracted with two 50 mL portions of dichloromethane. The combined dichloromethane layers were washed with water, dried over sodium sulfate, filtered, and concentrated in vacuo to give 1.3 g of 3-fluoro-2-nitrophenol as orange oil (61percent yield). An solution of 3-fluoro-2-nitrophenol (1.13 g, 7.2 mmol) and pyridine (0.65 mL, 8 mmol) in 15 mL of anhydrous dichloromethane was cooled in an ice bath and treated with a solution of triflic anhydride (1.33 mL, 7.9 mmol) in 3 mL of anhydrous dichloromethane. After 4 hours, the reaction mixture was diluted with 100 mL of dichloromethane, washed with two 30 mL portions of saturated aqueous sodium bicarbonate, two 30 mL portions of 1 N aqueous sulfuric acid, and two 30 mL portions of water, dried over sodium sulfate, filtered, and concentrated in VACUA TAO give 2 g of the title product as a light brown oil (96percent yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
27% | at 15 - 26℃; for 1.5 - 2 h; | 3-Fluorophenol (5Og, 446mmol, lequiv) is dissolved glacial acetic acid (250 mL) and nitric acid 99percent (29.8g, 468mmol, 1.05equiv) is added slowly over approximately 1 h, maintaining the temperature at 20-250C. After complete addition, the reaction mixture is stirred for 30-60 min at ambient temperature and disappearance of 3-fluorophenol is confirmed by HPLC. The mixture is quenched by addition of water (500 mL). The resulting mixture is extracted with cyclohexane (4*67mL) to remove most of the regioisomers. The combined organic phases are extracted with water (167mL) to recover any desired regioisomer. The combined aqueous phases are extracted with TBME (3*167 mL) TBME to recover the desired product. The TBME phase, containing the desired regioisomer, is washed with a 10percent solution of sodium carbonate (4* 10OmL) to remove any acetic acid.TBME is replaced by toluene by distillation at atmospheric pressure, resulting in a solution of the product in approximately 100 mL of toluene. The solution is slowly cooled down to ambient temperature, which led to the precipitation of the desired product. The product was collected by filtration. The solid was dried in an oven overnight to give the title compound in 29percent yield and 97.9percent purity by HPLC. 1H-NMR (399.822 MHz, DMSO) δ 11.49 (s, IH), 8.07 (m, IH), 6.84-6.76 (m, 2H). 19F-NMR (376.209MHz, DMSO) δ - 114.28. m/z LCMS (ESI -ve) 156.00 (M-H); Method B: 3-Fluorophenol (1 mol equiv) is dissolved glacial acetic acid (2.5 rel vol) and nitric acid99percent (1.16 mol equiv) is added slowly over approximately 1 h, maintaining the temperature at 20-250C. After complete addition, the reaction mixture is stirred for Ih at ambient temperature and disappearance of 3-fluorophenol is confirmed by HPLC. The mixture is quenched by addition of water (2.5 rel vol). The resulting mixture is extracted 7 times with cyclohexane (1.675 rel vol) to remove most of the regioisomers. The combined organic phases are extracted with water (1 rel vol) to recover any desired regioisomer. The <n="21"/>combined aqueous phases are extracted twice with TBME (2.5 rel vol) to recover the desired product. The combined TBME phases, containing the desired regioisomer, are washed three times with a solution of 3percent aqueous potassium carbonate (1.25 rel vol) to remove any acetic acid. The TBME solution is concentrated at atmospheric pressure, then activated charcoal (0.017 rel weight) is added along with toluene (4.0 rel vol). The TBME is totally removed by atmospheric distillation. The warm solution at 50-800C is filtered over a filteraid to remove any insoluble particles. The toluene solution is then cooled to 0-50C which led to the precipitation of the desired product which was collected by filtration. The crude product was washed with toluene (0.17 rel vol) and petroleum ether (0.25 rel vol). The solid was dried in an oven overnight to give the title compound in 27percent yield and 97.4percent purity by HPLC.Crude 3-fluoro-4-nitrophenol (1 mol eq) is heated up to 110-115°C in toluene (3.24 rel vol) for 30 minutes. The mixture is cooled to 80-1000C and filtered over filteraid to remove any insoluble particles. The solution is further cooled to 0-50C which led to the precipitation of the desired product which was collected by filtration. The crude product was washed with toluene (0.17 rel vol). The solid was dried in an oven overnight to give the title compound in 77percent yield (recrystallisation only) and 99.2percent purity by HPLC. 1H-NMR (399.822 MHz, DMSO) δ 11.49 (s, IH), 8.07 (m, IH), 6.84-6.76 (m, 2H). 19F-NMR (376.209MHz, DMSO) δ -114.28. m/z LCMS (ESI -ve) 156.00 (M-H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
27% | at 15 - 26℃; for 1.5 - 2 h; | 3-Fluorophenol (5Og, 446mmol, lequiv) is dissolved glacial acetic acid (250 mL) and nitric acid 99percent (29.8g, 468mmol, 1.05equiv) is added slowly over approximately 1 h, maintaining the temperature at 20-250C. After complete addition, the reaction mixture is stirred for 30-60 min at ambient temperature and disappearance of 3-fluorophenol is confirmed by HPLC. The mixture is quenched by addition of water (500 mL). The resulting mixture is extracted with cyclohexane (4*67mL) to remove most of the regioisomers. The combined organic phases are extracted with water (167mL) to recover any desired regioisomer. The combined aqueous phases are extracted with TBME (3*167 mL) TBME to recover the desired product. The TBME phase, containing the desired regioisomer, is washed with a 10percent solution of sodium carbonate (4* 10OmL) to remove any acetic acid.TBME is replaced by toluene by distillation at atmospheric pressure, resulting in a solution of the product in approximately 100 mL of toluene. The solution is slowly cooled down to ambient temperature, which led to the precipitation of the desired product. The product was collected by filtration. The solid was dried in an oven overnight to give the title compound in 29percent yield and 97.9percent purity by HPLC. 1H-NMR (399.822 MHz, DMSO) δ 11.49 (s, IH), 8.07 (m, IH), 6.84-6.76 (m, 2H). 19F-NMR (376.209MHz, DMSO) δ - 114.28. m/z LCMS (ESI -ve) 156.00 (M-H); Method B: 3-Fluorophenol (1 mol equiv) is dissolved glacial acetic acid (2.5 rel vol) and nitric acid99percent (1.16 mol equiv) is added slowly over approximately 1 h, maintaining the temperature at 20-250C. After complete addition, the reaction mixture is stirred for Ih at ambient temperature and disappearance of 3-fluorophenol is confirmed by HPLC. The mixture is quenched by addition of water (2.5 rel vol). The resulting mixture is extracted 7 times with cyclohexane (1.675 rel vol) to remove most of the regioisomers. The combined organic phases are extracted with water (1 rel vol) to recover any desired regioisomer. The <n="21"/>combined aqueous phases are extracted twice with TBME (2.5 rel vol) to recover the desired product. The combined TBME phases, containing the desired regioisomer, are washed three times with a solution of 3percent aqueous potassium carbonate (1.25 rel vol) to remove any acetic acid. The TBME solution is concentrated at atmospheric pressure, then activated charcoal (0.017 rel weight) is added along with toluene (4.0 rel vol). The TBME is totally removed by atmospheric distillation. The warm solution at 50-800C is filtered over a filteraid to remove any insoluble particles. The toluene solution is then cooled to 0-50C which led to the precipitation of the desired product which was collected by filtration. The crude product was washed with toluene (0.17 rel vol) and petroleum ether (0.25 rel vol). The solid was dried in an oven overnight to give the title compound in 27percent yield and 97.4percent purity by HPLC.Crude 3-fluoro-4-nitrophenol (1 mol eq) is heated up to 110-115°C in toluene (3.24 rel vol) for 30 minutes. The mixture is cooled to 80-1000C and filtered over filteraid to remove any insoluble particles. The solution is further cooled to 0-50C which led to the precipitation of the desired product which was collected by filtration. The crude product was washed with toluene (0.17 rel vol). The solid was dried in an oven overnight to give the title compound in 77percent yield (recrystallisation only) and 99.2percent purity by HPLC. 1H-NMR (399.822 MHz, DMSO) δ 11.49 (s, IH), 8.07 (m, IH), 6.84-6.76 (m, 2H). 19F-NMR (376.209MHz, DMSO) δ -114.28. m/z LCMS (ESI -ve) 156.00 (M-H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | Stage #1: With tin(II) chloride dihdyrate; water In tetrahydrofuran at 80℃; for 0.666667 h; Stage #2: With sodium hydrogencarbonate In tetrahydrofuran; water; ethyl acetate |
Step 1. 2-amino-3-fluorophenolStannous chloride, dihydrate (0.724 g, 3.18 mmol) was added to a solution of 3-fluoro-2-nitrophenol (0.100 g, 0.636 mmol, SynQuest) in THF (5.0 mL), and water (5.0 mL) and the mixture was heated to 80° C. for 40 min. Upon cooling to RT, the reaction was diluted with ethyl acetate and saturated sodium bicarbonate solution. The mixture was then filtered to remove the insoluble material and the layers were separated. The aqueous layer was extracted with ethyl acetate three times. The extracts were washed with brine, dried over sodium sulfate, decanted and concentrated to afford product which was used without further purification (65 mg, 80percent). LCMS (M+H)+: 128.0. |
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