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CAS No. : | 51446-30-1 | MDL No. : | MFCD01862084 |
Formula : | C7H5FO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | CZNFABVUVHWEJF-UHFFFAOYSA-N |
M.W : | 156.11 | Pubchem ID : | 2774480 |
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 : | 2.0 |
Molar Refractivity : | 35.38 |
TPSA : | 57.53 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) : | -6.09 cm/s |
Log Po/w (iLOGP) : | 0.76 |
Log Po/w (XLOGP3) : | 1.64 |
Log Po/w (WLOGP) : | 1.65 |
Log Po/w (MLOGP) : | 1.42 |
Log Po/w (SILICOS-IT) : | 1.16 |
Consensus Log Po/w : | 1.33 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -2.18 |
Solubility : | 1.03 mg/ml ; 0.00663 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.46 |
Solubility : | 0.54 mg/ml ; 0.00346 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -1.46 |
Solubility : | 5.4 mg/ml ; 0.0346 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.16 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338-P310 | 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 |
---|---|---|
91% | With lithium hydroxide monohydrate In tetrahydrofuran; water at 20℃; for 16 h; | STEP 1 : 2-FLUORO-5-HYDROXYBENZOIC ACID [00248] To a solution of methyl 2-fluoro-5-hydroxybenzoate (30.0 g, 176.47 mmol, 1.0 equiv, F-chemicals) in THF:H20 (3: 1, 350 mL) was added LiOH.H20 (22.2 g, 529.41 mmol, 3.0 equiv) at room temperature. The reaction mixture was stirred for 16 h at room temperature. The THF was removed from the reaction mixture, diluted with cold water; pH was adjusted to about 3 with 1.5 N aqueous HC1, extracted with EtOAc (3 x 250 mL). The combined extracts were washed with brine (150 mL), dried over anhydrous Na2S04, filtered and evaporated to afford 2-fluoro-5-hydroxybenzoic acid as an off white solid (25.1 g, 91 percent> yield). MS m/z: [M- 1]"= 155.4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | Stage #1: for 1 h; Reflux Stage #2: Reflux |
Na2CO3 (1 eq.) was added to a degassed souUon of water (0.35 M) and the appropriatebromobenzoc acid (1 eq.) and was refluxed for 30 minutes. A further portion of Na2CO3 (1.5eq.) was added to the reaction and refluxed for a further 30 mnutes. Separat&y CuBr2 (0.1 eq.) and trans-N, W-dmethycycohexane-1 ,2-damne (0.2 eq.) were added to degassed water (0.04 M) and an ntense bue coour was observed. This mixture was added to the refluxng aqueous souton and aflowed to sUr at this temperature overnight. The resuWngsouton was aflowed to coo to room temperature and was acid Wed with conc. HC and extracted nto EtOAc. The organcs were dried with MgSO4, ffltered, and the sovent removed in vacuo to give the desired product.The foHowng compounds were made by the Uflmann transformaUon method A Al)H5bromo-2- fluorobenzoc acid (3.5g, 15.98 mmo)Off whte sohd (2.16g, 87percent yed). 1H NMR(400 MHz, DM80) 6 7.18 (dd, J = 6.0, 3.2Hz, 1H), 7,09 (dd, J= 10.5, 8.9 Hz, 1H), 6.98 6.93 (m, 1H). LCM8 B rt 3.19 mn, m/z157.1 [M + H]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | Reflux | A solution of 2-fluoro-5-hydroxybenzoic acid (1.5 g, 9.6 mmol) and conc. H2SO4 (0.050 mL, 0.92 mmol) in MeOH (10 mL) was stirred at reflux ON. After evaporation of the solvent, the residue was dissolved in 1N NaOH and extracted 3x with EtOAc. The combined extracts were dried over Na2SO4, filtered and evaporated to give 24B (1.47 g, 90percent yield) as a colorless solid which was used without further purification in the following reaction.1H NMR (500MHz, CDCl3) δ 7.39 (dd, J=5.5, 3.3 Hz, 1H), 7.08 - 7.03 (m, 1H), 7.03 - 6.98 (m, 1H), 3.95 (s, 3H). |
833 mg | at 0℃; for 2 h; Inert atmosphere; Reflux | The obtained 2-fluoro-5-hydroxybenzoic acid (3e) (780 mg, 5 mmol) was dissolved in 100 mL methanol. 1. Thionyl chloride (0.8 mL, 10 mmol) was added dropwise under the condition of ice bath (0°C) and stirring, and then refluxed for two hours. The reaction solution was concentrated, and then column chromatography (petroleum ether : ethyl acetate = 2:1) was performed to isolate methyl 2-fluoro-5-hydroxybenzoate (3f), 833 mg white solid (yield 98percent). 1H NMR (600 MHz, DMSO-d6) δ 9.73 (s, 1H), 7.20-7.18 (m, 1H), 7.13-7.09 (m, 1H), 6.99- 6.97 (m, 1H), 3.80 (s, 3H); ESI-MS m/z: calculated for 170.04, found 171.25 [M+H]+. |
833 mg | at 0℃; for 2 h; Reflux | The obtained 2-fluoro-5-hydroxybenzoic acid (3e) (780 mg, 5 mmol) was dissolved in 100 mL methanol. Thionyl chloride (0.8 mL, 10 mmol) was added dropwise under the condition of ice bath (0° C.) and stirring, and then refluxed for two hours. The reaction solution was concentrated, and then column chromatography (petroleum ether:ethyl acetate=2:1) was performed to isolate methyl 2-fluoro-5-hydroxybenzoate (3f), 833 mg white solid (yield 98percent). 1H NMR (600 MHz, DMSO-d6) δ 9.73 (s, 1H), 7.20-7.18 (m, 1H), 7.13-7.09 (m, 1H), 6.99-6.97 (m, 1H), 3.80 (s, 3H); ESI-MS m/z: calculated for 170.04. found 171.25 [M+H]+. |
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