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CAS No. : | 56874-97-6 | MDL No. : | MFCD12913381 |
Formula : | C7H6FNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OBFYYFBQCWHDRP-UHFFFAOYSA-N |
M.W : | 155.13 g/mol | Pubchem ID : | 13726282 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 36.52 |
TPSA : | 63.32 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) : | -6.15 cm/s |
Log Po/w (iLOGP) : | 1.32 |
Log Po/w (XLOGP3) : | 1.55 |
Log Po/w (WLOGP) : | 1.05 |
Log Po/w (MLOGP) : | 1.02 |
Log Po/w (SILICOS-IT) : | 0.92 |
Consensus Log Po/w : | 1.17 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.12 |
Solubility : | 1.19 mg/ml ; 0.00766 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.49 |
Solubility : | 0.503 mg/ml ; 0.00324 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -1.68 |
Solubility : | 3.27 mg/ml ; 0.0211 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.01 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
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* 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 |
---|---|---|
93% | With potassium carbonate; In N,N-dimethyl-formamide; at 90℃; for 2.0h; | To a solution of 5-fluoro-2-hydroxy-benzamide (13)(1.16g, 7.5mmol) in DMF (3OmL) was added potassium carbonate (2.2g, 16.0mmol) followed by methyl (4-bomomethyl) benzoate (1.82g, δ.Ommol), The mixture was heated for 2 hours at 900C. The reaction was then cooled to ambient temperature, a fine white suspension resulted. The reaction was concentrated in vacuo and the resultant cream precipitate was washed with water (2x 30ml) and then plug washed with diethyl ether (2x 25ml) and dried to afford a white solid. Single peak in LC-MS analysis, (2.2Og, 93% yield) requiring no further purification; m/z (LC-MS, ESP), RT=3.56min, (M+H)=304.0. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With ammonia; In methanol; at 50℃; for 10h;Autoclave; | A mixture of <strong>[391-92-4]methyl 5-fluoro-2-hydroxybenzoate</strong> (22 g, 129 mmol) and methanolic ammonia (250 mL) was heated at 50 °C in an autoclave for 1 0 h. The reaction mixture was concentrated under reduced pressure, the resulting crude was codistilled with toluene and dried to give 5-fluoro-2- hydroxybenzamide as a brown solid (18.5 g, 92percent). LS-MS m/z: 1 54.0 (M-H). 1 H NMR (400 MHz, DMSO-d6): delta ppm 1 2.74 (s, 1 H), 8.40 (s, 1 H), 8.03 (s, 1 H), 7.73-7.71 (m, 1 H), 7.31 -7.29 (m, 1 H), 6.91 -6.90 (m, 1 H). |
92% | With ammonia; In methanol; at 50℃; for 10h;Autoclave; | A mixture of <strong>[391-92-4]methyl 5-fluoro-2-hydroxybenzoate</strong> (22 g, 129 mmol)and methanolic ammonia (250 mL)was heated at 50°C in an autoclave for 10 h. The reaction mixture was concentrated under reducedpressure, the resulting crude was codistilled with toluene and dried to give 5-fluoro-2-hydroxybenzamide as a brown solid (1 8.5 g, 92percent yleld). LC-MS m/z 154.0 (M-H). 1H NMR (400 MHz, DMSO-d6) 6 ppm 12.74 (5, 1H), 8.40 (5, 1H), 8.03 (5, 1H), 7.73-7.71 (m, 1H), 7.31-7.29 (m, 1H), 6.91-6.90 (m, 1H). |
With ammonia; In methanol; at 60℃; | (a) 5-Fluoro-2-hydroxy-benzamide (193) To a screw tight 50 mL pressure vessel was added <strong>[391-92-4]methyl 5-fluoro-2-hydroxybenzoate</strong> (1.0 g, 5.88 mmol) and (7N) ammonia in methanol (15 ml). The pressure vessel was sealed and contents stirred over night at 60° C. The reaction was cooled to room temperature and the solution evapourated to dryness to afford white crystalline solid. Single peak in LC-MS (0.91 g, 100percent purity); m/z (LC-MS, ESP), RT=2.94 mins, (M+H) 156. |
With ammonia; In water; at 50℃; for 60h; | 5-Fluoro-2-hydroxybenzamide; Methyl 5-fluoro-2-hydroxybenzoate was dissolved in 37percent NH3/aq ( 2OmL) and stirred at 50°C for 60 hours. The solution was concentrated, diluted with ethylacetate (2OmL) and washed with brine. The product was used in the next step without any further purification. APCI-MS m/z: 156.0 [MH+]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With potassium carbonate; In N,N-dimethyl-formamide; at 90℃; for 1.0h; | (d) 4-[5-(2-Carbamoyl-4-fluoro-phenoxymethyl)-2-fluoro-benzoyl]-piperazine-1-carboxylic acid tert-butyl ester (196) To a solution of 4-(2-fluoro-5-methanesulfonyloxymethyl-benzoyl)-piperazine-1-carboxylic acid tedt-butyl ester (195)(0.832 g, 2.0 mmol) in DMF (3mL) under a nitrogen blanket was added 5-fluoro-2-hydroxy-benzamide (193)(0.31 g, 2.0 mmol), followed by potassium carbonate (0.552 g, 4.0 mmol). The mixture was then heated to 90 C. After 1 hour of heating the reaction was cooled to 45 C. water (4 mL) was added. The reaction was then cooled to 0 C. with stirring. A fine white suspension resulted. The solid was filtered, washed with cold water (2*10 mL), hexane (2*10 mL) and TBME (2*10 ml). The dried solid provided single peak in LC-MS (0.548 g, 57% yield) and taken through to next step without need for any purification; m/z (LC-MS, ESP), RT=3.18 mins, (M+H) 476. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; thionyl chloride; In 5,5-dimethyl-1,3-cyclohexadiene; ethanol; | a) 6-Fluoro-2-(5-fluoro-2-hydroxyphenyl)benz[e][1,3]oxazin4-one: 4.3 g of 5-fluoro-salicylamide and 4.7 g of 5-fluorosalicylic acid are boiled under reflux in 50 ml of xylene after addition of 0.3 ml of pyridine. 4.4 ml of thionyl chloride are added in the course of 2 h, the mixture is stirred for a further 1 h and the solvent is then distilled off under reduced pressure. The residue is suspended in 30 ml of ethanol, filtered off and washed with ethanol. After drying, 6-fluoro-2-(5-fluoro-2-hydroxyphenyl)benz[e][1,3]oxazin-4-one is obtained as slightly yellow crystals of m.p. 250-252 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Aryl ether formation: 5-Fluoro-2-({(2S)-2-[(mesitylsulfonyl)aminoJpropyl}oxy)benzamide; (2S)-2-[(Mesitylsulfonyl)amino]propyl 2,4,6-trimethylbenzenesulfonate (263mg, 0.6mmole) was added to a slurry containing Cs2CO3 (487mg, 1.5mmole) and 5-fluoro-2- hydroxybenzamide (app. lmmole) in 2.5mL DMF. The reaction mixture was stirred overnight in room teperature before it was diluted with ethylacetate (2OmL) and washed with IM HCl/aq. The organic layer was dried, concentrated and purified on HPLC-C18.1H NMR (299.946 MHz5 DMSO) δ 7.79 (d, J= 8.4 Hz, IH), 7.63 (s, 2H), 7.50 (dd, J= 9.5, 3.3 Hz, IH), 7.20 (ddd, J= 9.1, 7.7, 3.4 Hz, IH), 6.99 - 6.88 (m, 3H), 3.87 (d, J= 5.9 Hz, 2H), 3.56 - 3.45 (m, IH), 2.50 (s, 6H), 2.18 (s, 3H), 0.93 (d, J= 6.8 Hz, 3H) APCI-MS m/z: 395.2 [MH+]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With potassium carbonate; In N,N-dimethyl-formamide; at 90℃; for 3.0h; | (e) 4-{5-[1-(2-Carbamoyl-4-fluoro-phenoxy)-ethyl]-2-fluorobenzoyl}-piperazine-1-carboxylic acid Tert-Butyl Ester8; To a solution of 4-[5-(1-chloro-ethyl)-2-fluoro-benzoyl]-piperazine-1-carboxylic acid tert-butyl ester (6) (0.36 g, 0.84 mmol) in DMF (10 ml) was added 5-fluoro-2-hydroxy-benzamide (7) (0.18 mg, 1.16 mmol) and potassium carbonate (0.32 g, 2.3 mmol). The mixture was then heated to 90 C. for 3 hours and then cooled to ambient temperature. The reaction was then diluted with water (15 ml) and extracted with ethyl acetate (2×10 ml). The combined organics were dried over magnesium sulfate, filtered and then concentrated in vacuo to afford a pale yellow solid. The material was subjected to flash chromatography (eluent: hexane/ethyl acetate, 1:2, Rf 0.3). A white solid (8) was isolated. Single peak in LC-MS analysis. (250 mg, 53% yield); m/z (LC-MS, ESP), RT=4.44 mins, (M+1) 490.0. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | In tetrahydrofuran; at 0 - 20℃; for 14.0h; | To a stirred solution of <strong>[56874-97-6]5-fluoro-2-hydroxybenzamide</strong> (8.0 g, 51 .6 mmol)in dry THF (80 mL), 1,1’-carbonyldiimidazole (10.9 g, 67.09 mmol)was added at 000. The mixture was stirred at room temperaturefor 14 h then was concentrated under reduced pressure. The resulting crude was treated with MeOH and washed with diethyl ether. The resulting white solid was dried and used in the next step without further purification (5.1 g, 55% yleld, white solid). LC-MS mlz 180.0 (M-H). 1H NMR (400 MHz, DMSO-d6) 6 ppm 12.19 (5, 1H), 7.68-7.67 (m, 2H),7.50-7.48 (m, 1H). |
In tetrahydrofuran; at 0 - 20℃; for 14.0h; | To a stirred solution of <strong>[56874-97-6]5-fluoro-2-hydroxybenzamide</strong> (8.0 g, 51 .6 mmol) in dry THF (80 mL), 1 ,1 '-carbonyldiimidazole (10.9 g, 67.09 mmol) was added at 0C. The mixture was stirred at room temperature for 14 h then was concentrated under reduced pressure. The resulting crude was treated with MeOH and washed with diethyl ether. The resulting white solid was dried and used in the next step without further purification (5.1 g, 55% white solid). LS- MS m/z: 180.0 (M-H): 1 H NMR (400 MHz, DMSO-d6): δ ppm 1 2.19 (s, 1 H), 7.68-7.67 (m, 2H), 7.50-7.48 (m, 1 H). |
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