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CAS No. : | 1583-58-0 | MDL No. : | MFCD00011670 |
Formula : | C7H4F2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NJYBIFYEWYWYAN-UHFFFAOYSA-N |
M.W : | 158.10 | Pubchem ID : | 74102 |
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 : | 33.32 |
TPSA : | 37.3 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) : | -5.79 cm/s |
Log Po/w (iLOGP) : | 1.21 |
Log Po/w (XLOGP3) : | 2.07 |
Log Po/w (WLOGP) : | 2.5 |
Log Po/w (MLOGP) : | 2.47 |
Log Po/w (SILICOS-IT) : | 2.06 |
Consensus Log Po/w : | 2.06 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.85 |
Log S (ESOL) : | -2.46 |
Solubility : | 0.546 mg/ml ; 0.00345 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.48 |
Solubility : | 0.52 mg/ml ; 0.00329 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.32 |
Solubility : | 0.764 mg/ml ; 0.00483 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.2 |
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 |
---|---|---|
90% | With sodium hydroxide In dimethyl sulfoxide at 130℃; for 8 h; | Dimethyl sulfoxide (DMSO, 4 L) was added to a dry 10 L four-necked flask,2,4-Difluorobenzoic acid (500 g, 3.16 mol)And NaOH (253 g, 6.32 mol),And warmed to 130 , the reaction for about 8h,TLC detection,Until the reaction is complete, the reaction system was reduced to room temperature,The reaction solution was slowly poured into 40L ice water,With concentrated hydrochloric acid to adjust the pH to 2 ~ 3 (adjust the temperature of the process is not higher than 20 )A large number of solid precipitation, continue stirring 2h suction filtration, the filter cake was washed with an appropriate amount of water,Obtained as a white solid, dried at 60 ° C for 12h under reduced pressure to give 4-fluorosalicylic acid 450g, yield 90percent.mp 184.9 ~ 185.2 ° C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | at 80℃; for 24.25 h; | A. 2,4-Difluoro-benzoic acid ethyl ester. Into a solution of 2,4-difluorobenzoic acid (36.0 g, 228 mmol) in EtOH (250 mL) was bubbled HCl(g) for 15 min. The solution was heated to 80° C. and stirred for 24 h. The solution was partially concentrated and diluted with H2O (300 mL). The aqueous layer was extracted with EtOAc (3*300 mL). The combined organic layers were dried (MgSO4), filtered and concentrated to provide 27.2 g (76percent) of the title compound as a clear oil. MS (ESI): exact mass calculated for C9H8F2O2, 186.05; m/z not found. 1H NMR (400 MHz, CDCl3): 8.01-7.95 (m, 1H), 6.95-6.85 (m, 2H), 4.39 (q, J=7.1, 2H), 1.39 (t, J=7.1, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With thionyl chloride In methanol | 1 methyl 2,4-difluorobenzoate A solution of 2,4-difluorobenzoic acid (1.5808 g, 10.00 mmol) in methanol (15 ml) was cooled to 0° C. in ice-water bath. To the mixture was added dropwise a solution of thionyl chloride (1.46 ml, 20.02 mmol) in methanol (10 ml). The mixture was gradually warmed to room temperature and stirred for 24 hours. The mixture was added to sat. NaHCO3 aqueous solution, extracted three times with ether and dried over MgSO4. The mixture was concentrated and purified by silica gel chromatography (hexane/ether=5/1) to give the title compound (1.6743 g; 97percent). 1H-NMR(CDCl3) 7.99 (td, 1H, J=8.2, 6.6 Hz), 6.98-6.84 (m, 2H), 3.93 (s, 3H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88 g | at 60℃; for 8 h; | Sulphuric acid (97.4g) was added to a mixture of 2,4-diflourobenzoic acid (100 g) and methanol (1 L) at ambient temperature. The reaction mixture was heated to 60°C and maintained at that temperature for 8 hours. After cooling to room temperature, water (500 mL) was added. The reaction mixture was slowly added to chilled water (500 mL). The organic layer was separated and the aqueous layer was thrice extracted with dichloromethane (500 mL x 3). The combined dichloromethane layers were washed with 10percent sodium bicarbonate solution (200 mL) then concentrated under vacuum at temperature of not more than (NMT) 50-55°C to give methyl 2,4-difluorobenzo ate (88 g, Yield: 0.8w/w). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | at 0 - 20℃; for 16.5 h; | Step A To a suspension of 2,4-difluorobenzoic acid (9.985 g, 63.2 mmol) in concentrated sulfuric acid (30 mL) at 0° C. was added fuming nitric acid (30 mL) over 30 min. The mixture was allowed to warm to RT and stirred for an additional 16 h. The homogeneous mixture was poured onto ice and extracted with ethyl acetate. The organic extract was washed with water, dried and concentrated in vacuo to afford 2,4-difluoro-5-nitrobenzoic acid (12.56 gm, 98percent) as pale yellow solid. |
98% | With sulfuric acid; nitric acid In water at 20 - 50℃; for 3.5 h; | Nitric Acid (120 mL) was added slowly to a cold solution of sulfuric acid (200 mL) 2,4- difluorobenzoic acid (65 g, 0 41 mol, 1 equiv) was added portionwise over 1 5 h and the reaction allowed to warm to RT The reaction mixture was heated to 50 0C for 2h and then poured slowly onto ice The product was extracted into ethyl acetate, dried over Na2SO4, filtered and concentrated to give intermediate 17 (82 g, 98percent yield) as a yellow solid 1H NMR (400 MHz, DMSO-cfe) δ ppm 8 56 (t, J=I 87 Hz, 1 H), 7 82 (t, J=10 71 Hz, 1 H) |
98% | at 0 - 20℃; for 16.5 h; | A) To a suspension of 2,4-difluorobenzoic acid (9. 985 g, 63.2 mmol) in concentrated sulfuric acid (30 [ML)] at [0 °C] was added fuming nitric acid (30 [ML)] over 30 min. The mixture was allowed to warm to RT and stirred for additional 16 h. The homogeneous mixture was poured over ice and extracted with ethyl acetate. The organic extract was washed with water, dried and concentrated in vacuo to afford 2,4- difluoro-5-nitrobenzoic acid (12.56 gm, 98percent) as pale yellow solid. |
98% | at 20 - 50℃; for 3.5 h; | The synthesis of intermediate 22; <n="23"/>Intermediate 16; 2,4-difluoro-5-nitrobenzoic acid; F O; Nitric Acid (120 ml.) was added slowly to a cold solution of sulfuric acid (200 mL). 2,4-difluorobenzoic acid (65 g, 0.41 mol, 1 equiv) was added portioπwise over 1.5 h and the reaction allowed to warm to RT. The reaction mixture-was heated to 50 0C for 2h and then poured slowly onto ice. The product was extracted into ethyl acetate, dried over Na2SO4, filtered and concentrated to give intermediate 16 (82 g, 98percent yield) as a yellow solid.1H NMR (400 MHz, DMSO-CZ6) δ ppm 8.56 (t, J=I, .87 Hz, 1 H), 7.82 (t, ./=10.71 Hz, 1 H). |
98% | at 20 - 50℃; for 3.5 h; | Intermediate 1; 2,4-difluoro-5-nitrobeπzoic acid; Nitric Acid (120 mL) was added slowly to a cold solution of sulfuric acid (200 mL). 2,4- difluorobenzoic acid (65 g, 0.41 mol, 1 equiv) was added portionwise over 1.5 h and the reaction allowed to warm to RT. The reaction mixture was heated to 50 0C for 2h and then poured slowly onto ice. The product was extracted into ethyl acetate, dried overNa2SO4, filtered and concentrated to give intermediate 1 (82 g, 98percent yield) as a yellow solid.1H NMR (400 MHz, DMSO-dβ) δ ppm 8.56 (t, J=7.87 Hz, 1 H), 7.82 (t, J=10.71 Hz, 1 H). |
61% | With nitric acid In sulfuric acid | 2,4-Difluoro-5-nitrobenzoic acid 2,4-Difluorobenzoic acid (5 g, 0.031 M) was dissolved in concentrated sulfuric acid (30 ml), and cooled to 0°. The mixture was stirred, and fuming nitric acid (d 1.567 g/ml, 1.91 ml, 0.047 M) added dropwise, keeping the temperature below 5°. After stirring for 3 hours, the mix was poured onto ice, and organics extracted into dichloromethane (2*75 ml). The combined organic layers were washed with water, dried (MgSO4), and evaporated to give 2,4-difluoro-5-nitrobenzoic acid (3.9 g, 61percent). Nmr (DMSO-d6): δ7.18 (t, 1H); 8.88 (t, 1H); 9.93 (br, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | Stage #1: With n-butyllithium; diisopropylamine In tetrahydrofuran at -78℃; Stage #2: at -78 - 25℃; Stage #3: With water; ammonium chloride In tetrahydrofuran |
To a stirred solution of diisopropylamine (1.7 g, 16.4 mmol) in THF 2.6 M solution of n-BuLi (1.1 g, 16.4 mmol) was added at -30°C and the mixture was stirred for an hour at the same temperature. To this mixture a solution of 2,4-difluorobenzoic acid (1.0 g, 6.3 mmol) in THF was added slowly at -78°C, followed by methyl iodide (2.2 g, 15.7 mmol) and it was stirred for another 2 h at the same temperature and allowed to attain the room temperature. The reaction mixture was treated with saturated aqueous NH4Cl solution and the aqueous layer extracted with ethylacetate (3 x 25 mL). The organic phases were combined and dried over anhydrous sodium sulfate. After removal of solvent, the residue was purified over a silica gel flash column using a gradient of ethyl acetate in pet. ether to give product as a white solid. Yield: 0.77 g (70percent) MS (ES) MH+: 172 for C8H6F2O2 1H NMR (400 MHz, CDCl3) δ: 2.2 (s, 3H), 7.0 (m, 1H), 7.9 (m, 1H). |
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