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CAS No. : | 63878-73-9 | MDL No. : | MFCD02683502 |
Formula : | C7H6FNO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | IFIOUOYJVOSTFH-UHFFFAOYSA-N |
M.W : | 171.13 | Pubchem ID : | 4437169 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.14 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 41.35 |
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) : | -6.66 cm/s |
Log Po/w (iLOGP) : | 1.27 |
Log Po/w (XLOGP3) : | 0.97 |
Log Po/w (WLOGP) : | 1.49 |
Log Po/w (MLOGP) : | 0.78 |
Log Po/w (SILICOS-IT) : | -0.05 |
Consensus Log Po/w : | 0.89 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.75 |
Solubility : | 3.04 mg/ml ; 0.0178 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.94 |
Solubility : | 1.94 mg/ml ; 0.0114 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.88 |
Solubility : | 2.25 mg/ml ; 0.0131 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.71 |
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 |
---|---|---|
99% | at 0℃; for 3 h; | Example 29 - Preparation of 7-chloro-A/-(3-((diethylamino)methyl)-4- fluorophenyl)quinolin-4-amine (compound 84); Step A: (2-Fluoro-5-nitro-phenyl)-methanol; To a solution of 2-fluoro-5-nitro-benzaldehyde (1000mg, 5.91 mmoles) in MeOH (10mL) was added NaBH4 (182mg, 4.82mmoles). The reaction mixture was stirred for 3h at 0°C. The reaction mixture was acidified with HCI 1 M until pH4, concentrated. 50mL of water was added and the compound was extracted with Et20. The organic layer was dried over MgS04, filtered, evaporated. Expected compound was obtained as a pale yellow solid (1007 mg, 99percent yield), mp = 62-64 <C. H NMR (300 MHz, CDCI3) δ 8.43 (dd, 6-CH, J= 6.2Hz and 2.9Hz, 1 H), 8.19 (ddd, J= 9Hz, 4.5Hz and 2.9Hz, 1 H), 7.20 (dd, J= 9.0Hz and 9.0Hz, 1 H), 4.85 (d, J = 3.6Hz, 2H), 2.12 (s large, 1 H). 3C NMR (75 MHz, CDCI3) δ 125.0 (CH, d, J = 10.0Hz), 124.7 (CH, d, J= 6.9Hz), 1 16.2 (CH, d, J= 23.6Hz), 58.2 (CH2). |
99.8% | at 0 - 20℃; for 1 h; | Step 1 (2-Fluoro-5-nitrophenyl)methanol To a stirred solution of 2-fluoro-5-nitrobenzaldehyde (30 g, 177.5 mmol) in methanol (350 mL) NaBH4 (8.1 g, 213.01 mmol) was added portion wise at 0° C. The reaction mixture was allowed warm to room temperature and stirred for 1 h. After completion of the reaction as indicated by TLC, the solvents were removed by rotary evaporation. The residue was diluted with ice-cold water (100 mL) and the aqueous layer was extracted with EtOAc (3*150 mL), washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford (2-fluoro-5-nitrophenyl)methanol (30.3 g, yield: 99.8percent, LC-MS: 96.7percent) as an off-white solid. ES+, m/z 172.3 [M+1]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
4.5 g | With diethylamino-sulfur trifluoride In dichloromethane at -78℃; Inert atmosphere | To a solution of Compound 2 (6.2 g, 36.3 mmol) in anhydrous DCM (80 mL) was added DAST (11.7 g, 34.3 mmol) drop-wise at -78 °C under N2. The reaction mixture was stirred at rt for 2 h, and poured into a beaker containing 30 g of ice, decomposing any unreacted DAST. Mixture was extracted twice with 45 mL portions of DCM. The combined organic layer was washed with 50 mL of water, and dried over anhydrous magnesium sulfate. Evaporation to dryness under reduced pressure gives crude product which was purified by silica gel chromatography (eluted with PE: EA=froml00: 1 to 50: 1) to afford Compound 3. (4.5 g, yield: 71percent) |
3.9 g | With diethylamino-sulfur trifluoride In dichloromethane at -30 - 10℃; | Compound 127 (2-fluoro-5-nitro-phenyl)methanol (4.3 g, 25.1 mmol) was dissolved in dichloro- methane (50 mL). Diethylaminosulfur trifluoride (4.5 g, 27.9 mmol) was added drop wise to the mixture at -30°C. The mixture was stirred at 10° C for 4 hours. Methanol (10 mL) was added to the mixture and the mixture was further stirred at 10°C for 30 minutes. The mixture was washed with brine (30mL) and the aqueous layer was extracted with CH2C12 (2 x 30 mL). The combined organic layers were dried over Na2S04 and concentrated in vacuo, resulting in l-fluoro-2-(fluoromethyl)-4-nitro- benzene (3.9 g). A mixture of l-fluoro-2-(fluoromethyl)-4-nitro-benzene (3.1 g, 17.9 mmol), iron (4.0 g, 71.6 mmol) and methanol (30 mL) was stirred at 65° for 8 hours. The mixture was filtrated and the filtrate was concentrated in vacuo, resulting in 4-fluoro-3-(fluoromethyl)aniline (1.5 g). 3-(chlorosulfonyl)benzoyl chloride (300 mg, 1.2 mmol) and triethylamine (150 mg, 1.5 mmol) were dissolved in dichloromethane (20 mL). 4-fluoro-3-(fluoromethyl)aniline (175 mg, 1.22 mmol) was added to the mixture at 0° C. The mixture was stirred at 10°C for 30 minutes. The mixture was used to the next step without further purification.Triethylamine (152 mg, 1.5 mmol) and 3-methyl-3-oxetanamine (131 mg. 1.5 mmol) were added to the above obtained reaction mixture at 0° C. The mixture was stirred at 20° C for 1 hour. The solvent was removed in vacuo and the obtained residue was purified by reversed phase high performance liquid chromatography (Column: Gemini 250*20mm*5um.. A: H2O+0.1percentTFA B: MeCN. 27percent to 57percent B in A). The product fractions were collected and the organic solvent was removed in vacuo. The fraction was neutralized by saturated NaHC03. The mixture was extracted with dichloromethane (3 x 20 mL) and the combined organic layer was dried over Na2S04 and concentrated in vacuo, resulting in compound 127 (91.1 mg). Method A; Rt: 4.95 min. m/z : 397.3 (M+H)+ Exact mass: 396.1. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.41 (s, 3 H) 4.14 (d, J=6.3 Hz, 2 H) 4.56 (d, J=6.3 Hz, 2 H) 5.52 (d, J=48 Hz, 2 H) 7.31 (t, J=9.4 Hz, 1 H) 7.72 - 7.89 (m, 2 H) 7.92-7.97 (m, 1 H) 8.03 (d, J=8.0 Hz, 1 H) 8.23 (d, J=7.8 Hz, 1 H) 8.39 (s, 1 H) 8.55 (s, 1 H) 10.67 (s, 1 H). |
3.9 g | With diethylamino-sulfur trifluoride In dichloromethane at -30 - 10℃; for 4 h; | Compound 127 (2-fluoro-5-nitro-phenyl)methanol (4.3 g, 25.1 mmol) was dissolved in dichloro- methane (50 mL). Diethylaminosulfur trifluoride (4.5 g, 27.9 mmol) was added drop wise to the mixture at -30°C. The mixture was stirred at 10° C for 4 hours. Methanol (10 mL) was added to the mixture and the mixture was further stirred at 10°C for 30 minutes. The mixture was washed with brine (30mL) and the aqueous layer was extracted with CH2C12 (2 x 30 mL). The combined organic layers were dried over Na2S04 and concentrated in vacuo, resulting in l-fluoro-2-(fluoromethyl)-4-nitro- benzene (3.9 g). A mixture of l-fluoro-2-(fluoromethyl)-4-nitro-benzene (3.1 g, 17.9 mmol), iron (4.0 g, 71.6 mmol) and methanol (30 mL) was stirred at 65° for 8 hours. The mixture was filtrated and the filtrate was concentrated in vacuo, resulting in 4-fluoro-3-(fluoromethyl)aniline (1.5 g). 3-(chlorosulfonyl)benzoyl chloride (300 mg, 1.2 mmol) and triethylamine (150 mg, 1.5 mmol) were dissolved in dichloromethane (20 mL). 4-fluoro-3-(fluoromethyl)aniline (175 mg, 1.22 mmol) was added to the mixture at 0° C. The mixture was stirred at 10°C for 30 minutes. The mixture was used to the next step without further purification.Triethylamine (152 mg, 1.5 mmol) and 3-methyl-3-oxetanamine (131 mg. 1.5 mmol) were added to the above obtained reaction mixture at 0° C. The mixture was stirred at 20° C for 1 hour. The solvent was removed in vacuo and the obtained residue was purified by reversed phase high performance liquid chromatography (Column: Gemini 250*20mm*5um.. A: H2O+0.1percentTFA B: MeCN. 27percent to 57percent B in A). The product fractions were collected and the organic solvent was removed in vacuo. The fraction was neutralized by saturated NaHC03. The mixture was extracted with dichloromethane (3 x 20 mL) and the combined organic layer was dried over Na2S04 and concentrated in vacuo, resulting in compound 127 (91.1 mg). Method A; Rt: 4.95 min. m/z : 397.3 (M+H)+ Exact mass: 396.1. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.41 (s, 3 H) 4.14 (d, J=6.3 Hz, 2 H) 4.56 (d, J=6.3 Hz, 2 H) 5.52 (d, J=48 Hz, 2 H) 7.31 (t, J=9.4 Hz, 1 H) 7.72 - 7.89 (m, 2 H) 7.92-7.97 (m, 1 H) 8.03 (d, J=8.0 Hz, 1 H) 8.23 (d, J=7.8 Hz, 1 H) 8.39 (s, 1 H) 8.55 (s, 1 H) 10.67 (s, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | for 2 h; Reflux | A mixture of 2-fluoro-5-nitrobenzyl alcohol 1 (2.00 g, 11.9 mmol), iron powder (3.72 g, 66.8 mmol) and hydrochloric acid (265.84 mg, 7.28 mmol) was heated under reflux for 2 h. The hot mixture was filtered in Celite and allowed to reach room temperature. This aqueous phase was then basified with a saturated solution of sodium bicarbonate and extracted with CH2Cl2. The organic layer was separated, dried (Na2SO4), filtered, and concentrated by rotary evaporation to obtain the crude product as brown solid (1.51 g, 10.7 mmol, 90percent yield). IR (KBr): 3568, 3410, 2930, 1628, 1512, 1439, 1358, 1036, 874, 818, 737 cm−1; 1H-NMR (CDCl3) δ: 7.26 (br s, 2H), 6.84 (t, J=9.2 Hz, 1H), 6.75–6.69 (m, 1H), 6.61–6.50 (m, 1H) 4.67 (s, 2H). |
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