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CAS No. : | 84832-01-9 | MDL No. : | MFCD07368850 |
Formula : | C8H5F2NO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | CIHHBTMZOLRCRL-UHFFFAOYSA-N |
M.W : | 217.13 | Pubchem ID : | 43449035 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.12 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 6.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 46.46 |
TPSA : | 72.12 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) : | -6.35 cm/s |
Log Po/w (iLOGP) : | 1.3 |
Log Po/w (XLOGP3) : | 1.8 |
Log Po/w (WLOGP) : | 2.5 |
Log Po/w (MLOGP) : | 1.69 |
Log Po/w (SILICOS-IT) : | 0.46 |
Consensus Log Po/w : | 1.55 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.42 |
Solubility : | 0.829 mg/ml ; 0.00382 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.93 |
Solubility : | 0.253 mg/ml ; 0.00117 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.42 |
Solubility : | 0.825 mg/ml ; 0.0038 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.96 |
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 |
---|---|---|
96% | Stage #1: With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; |
General procedure: Oxalyl chloride (1.1 eq.) was added to a suspension of carboxylic acid (1.0 eq.) in dry DCM (0.5 m). Some drops of DMF were added and the resulting mixture was stirred at room temperature until the gas formation was complete. An excess of MeOH was added to the solution and the solvent was evaporated under reduced pressure. The residual was dried in vacuo and the product was used without further purification. |
19 g | Reflux | Dissolve 2,6-difluoro-3-nitrobenzoic acid compound 2308 (20.0 g, 0.10 mol) in methanol (200 mL).Additional concentrated sulfuric acid (10 mL) was added and the mixture was heated at reflux overnight. After the reaction solution was rotovapped to remove methanol, water and ethyl acetate were added to the residue.The liquid was separated and the aqueous phase was extracted three times with ethyl acetate. The organic phases were combined, washed with saturated sodium bicarbonate, washed with water, saturated brine, and anhydrous sulfur.The sodium sulfate was dried and evaporated to dryness under reduced pressure to give the pale yellow solid compound 2309 (19.0 g, yield: 89percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | at 20℃; for 2 h; | Step 3: methyl 2,6-difluoro-3-nitrobenzoateTo a solution of methyl 2,6-difluorobenzoate (68.8 g, 0.4 mol) in con. H2SO4 (300 mL) was added potassium nitroperoxous acid (48.5 g, 0.48 mol) for three times and the resulting reaction mixture was stirred at room temperature for 2 hrs. The mixture was droped into ice-water (500 mL) and filtered. The solid was washed with water and dried to afford the desired product (89 g, 100percent).1H NMR (DMSC i): ? 8.49-8.43 (1H, m), 7.56-7.51 (1H, m), 3.95 (3H, s). |
100% | at 20℃; for 2 h; | The 2, 6 - difluoro-benzoic acid methyl ester (68.8g, 0.4 µM) dissolved in concentrated sulfuric acid (300 ml) in, addition of potassium nitrate (48.5g, 0 . 48 µM), continuing stirring at room temperature 2 hours. The resulting reaction solution is poured into crushed ice in slow, filtering, the resulting solid with a large number of washing and drying can be obtained as shown in the title compound (89g, 100percent) |
98% | at 0℃; for 1 h; | To a solution of compound 1 (21.0 g, 122.0 mmol) in concentrated sulfuric acid (50 mL) was added fuming nitric acid (8 mL) dropwise at 0 °C. After the reaction mixture was stirred at 0 °C for 1 h, it was poured into ice-water. The precipitate was collected by filtration and rinsed with water to give 2 (26.0 g, 98percent) as a white solid, mp 58–60 °C. 1H NMR (CDCl3): δ 8.25–8.22 (m, 1H), 7.15–7.11 (m, 1H), 4.01 (s, 3H). |
80.6% | at 0℃; for 0.5 h; | Fuming nitric acid (1 1 g, 174 mmol) was added to a solution of methyl 2,6- difluorobenzoate (25 g, 145 mmol) in concentrated sulfuric acid (50 ml_) at 0 °C, and the reaction was stirred for 30 min at 0°C. The reaction mixture was poured over ice-water. The precipitate was filtered to give the title compound 25.1 g (80.6 percent yield) 1H NMR (400 MHz, CDCI3) δ ppm 8.13-8.20 (m, 1 H), 7.02-7.10 (m, 1 H), 3.93 (s, 3H). |
64% | at 20℃; for 1 h; Cooling with ice | Sulfuric acid (37 mL) was slowly added to nitric acid (20 mL) under ice-cooling, and added methyl 2,6-difluorobenzoate (25.7 g,149 mmol), The reaction was gradually warmed to room temperature and stirring was continued for 1 hour. The reaction system was poured into ice-water and filtered to obtain a white solid compound P'(20.7 g, yield 64percent). |
64% | at 20℃; for 1 h; Cooling with ice | Sulfuric acid (37 mL) was slowly added to nitric acid (20 mL) under ice-cooling, and methyl 2,6-difluorobenzoate (25.7 g, 149 mmol) and the reaction was gradually allowed to warm to room temperature. Stirring was continued for 1 hour, The reaction system was poured into ice-water and filtered to give a white solid compound d (20.7g, yield 64percent) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With methanol In hexanes for 2 h; Cooling with water | [00175] Step A: A 1 L flask was charged with 2,6-difluoro-3-nitrobenzoic acid (17.0 g,83.7 mmol) and MeOH (170 mL, 0.5M). The flask was placed in a cold water bath, and an addition funnel charged with a 2M solution of trimethylsilyl ("TMS") diazomethane in hexanes (209 mL, 419 mmol) was attached to the flask. The TMS diazomethane solution was added slowly to the reaction flask over the course of 2 hours. A large excess of reagent was required in order for the reaction to reach completion as determined by the ceased evolution of N2 upon further addition of reagent. The volatiles were removed in vacuo to afford methyl 2,6-difluoro- 3-nitrobenzoate as a solid (18.2 g, 99percent). The material was taken directly onto Step B. |
99% | for 2 h; Cooling with cold water | A 1 L flask was charged with 2,6-difluoro-3-nitrobenzoic acid (17.0 g, 83.7 mmol) and MeOH (170 mL, 0.5M). The flask was placed in a cold water bath, and an addition funnel charged with a 2M solution of trimethylsilyl ("TMS") diazomethane in hexanes (209 mL, 419 mmol) was attached to the flask. The TMS diazomethane solution was added slowly to the reaction flask over the course of 2 hours. A large excess of reagent was required in order for the reaction to reach completion as determined by the ceased evolution of N2 upon further addition of reagent. The volatiles were removed in vacuo to afford methyl 2,6-difluoro-3-nitrobenzoate as a solid (18.2 g, 99percent). The material was taken directly onto Step B. |
99% | for 2 h; | Step A: A 1 L flask was charged with 2,6-difluoro-3-nitrobenzoic acid (17.0 g, 83.7 mmol) and MeOH (170 mL, 0.5M). The flask was placed in a cold water bath, and an <n="39"/>addition funnel charged with a 2M solution of trimethylsilyl ("TMS") diazomethane in hexanes (209 mL, 419 mmol) was attached to the flask. The TMS diazomethane solution was added slowly to the reaction flask over the course of 2 hours. A large excess of reagent was required in order for the reaction to reach completion as determined by the ceased evolution of N2 upon further addition of reagent. The volatiles were removed in vacuo to afford methyl 2,6-difluoro-3-nitrobenzoate as a solid (18.2 g, 99percent). The material was taken directly onto Step B. |
99% | for 2 h; Cooling with cold water | A 1 L flask was charged with 2,6-difluoro-3-nitrobenzoic acid (17.0 g, 83.7 mmol) and MeOH (170 mL, 0.5M). The flask was placed in a cold water bath, and an addition funnel charged with a 2M solution of trimethylsilyl ("TMS") diazomethane in hexanes (209 mL, 419 mmol) was attached to the flask. The TMS diazomethane solution was added slowly to the reaction flask over the course of 2 hours. A large excess of reagent was required in order for the reaction to reach completion as determined by the ceased evolution of N2 upon further addition of reagent. The volatiles were removed in vacuo to afford methyl 2,6-difluoro-3-nitrobenzoate as a solid (18.2 g, 99percent). The material was taken directly onto Step B. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With ammonium hydroxide In ethanol at 20℃; | Aqueous ammonia (13mL) was added a solution of the compound p '(32.55g, 150mmol) in ethanol (300mL) solution, stirred at room temperature overnight, and filtered to give a yellow solid compound q' (18.31g, yield 57percent). |
57% | With ammonium hydroxide In ethanol at 20℃; | Aqueous ammonia (13 mL) Was added to a solution of the compound d (32.55 g, 150 mmol) in ethanol (300 mL) Stirring at room temperature overnight, filtered to obtain yellow solid compound e (18.31 g, yield 57percent) |
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