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CAS No. : | 517920-69-3 | MDL No. : | MFCD03094270 |
Formula : | C6H6BrFN2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OZKZRRLKJAXHQA-UHFFFAOYSA-N |
M.W : | 205.03 | Pubchem ID : | 2773279 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 42.91 |
TPSA : | 52.04 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) : | -6.59 cm/s |
Log Po/w (iLOGP) : | 1.27 |
Log Po/w (XLOGP3) : | 1.35 |
Log Po/w (WLOGP) : | 2.19 |
Log Po/w (MLOGP) : | 2.02 |
Log Po/w (SILICOS-IT) : | 1.52 |
Consensus Log Po/w : | 1.67 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.41 |
Solubility : | 0.806 mg/ml ; 0.00393 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.04 |
Solubility : | 1.85 mg/ml ; 0.00902 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.82 |
Solubility : | 0.312 mg/ml ; 0.00152 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.7 |
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 |
---|---|---|
99% | With iron; ammonium chloride In tetrahydrofuran; water at 95℃; for 22 h; | Intermediate 14; 5 -bromo-3 -fluorobenzene- 1 ,2 -diamine; To a solution of 4-bromo-2-fluoro-6-nitroaniline (0.5 g, 2.1 mmol) in THF (4.6 mL), EtOH (4.6 mL) and H20 (1.5 mL) was added iron powder (0.6 g, 10.6 mmol) and ammonium chloride (0.17 g, 3.2 mmol). The resulting mixture was stirred at 95 °C for 22 hours. The mixture was cooled to room temperature and filtered through diatomaceous earth. The solid was washed with EtOH until no further color came through the filter. The filtrate was concentrated and the residue was dissolved in EtOAc, washed with H20 and brine, dried over Na2S04, filtered and concentrated to give the title compound (0.43 g, 99percent) as a brown, waxy solid. |
92% | With tin(ll) chloride In ethanol at 70℃; | 5.00 g (21.275 mmol) of 4-bromo-2fluoro-6-nitroaniline was dissolved in 190 ml ethanol, 19.20 g (85.100 mmol) of tin(II) chloride dihydrate was added and it was stirred overnight at 700C. After cooling, the mixture was concentrated in a rotary evaporator, water was added and it was made weakly alkaline with saturated aqueous sodium hydrogen carbonate solution. The mixture was extracted three times with ethyl acetate, the combined organic phases were dried over sodium sulfate and concentrated in a rotary evaporator. The residue was dried under high vacuum. We obtained 4.18 g (92percent of theor.) of the target compound, which was reacted further without further purification.LC-MS (method 3): R, = 1.29 min; MS (EIpos): m/z = 205 [M+H]+. 1H-NMR (400 MHz, DMSO-D6): δ [ppm] = 4.52 (sbr, 2H), 5.10 (sbr, 2H), 6.49-6.52 (m, 2H). |
1.69 g | With iron; ammonium chloride In tetrahydrofuran; ethanol; water at 90℃; for 2 h; | The 4 - bromo -2 - fluoro -6 - nitroaniline (1.5 g, 6.3 mmol), iron powder (1.8 g, 31.8 mmol) and ammonium chloride (5.1 g, 96.0 mmol) dissolved in ethanol (15 ml), tetrahydrofuran (15 ml) and water (5 ml) in the, and heated to 90 °C stirring 2 h. The reaction cooled to room temperature, filtered, the filtrate is concentrated, the crude product of the title compound obtained (1.69 g), without purification directly used for the next step reaction. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | at 20℃; for 28 h; | 4.00 g (19.509 mmol) of the compound from example 89A was dissolved in 100 ml ethanol and 2.42 g (19.509 mmol) of 2,3-dihydroxy-l,4-dioxane was added. The mixture was stirred for 4 h at room temperature and a further 2.42 g (19.509 mmol) of 2,3-dihydroxy-l,4-dioxane was added. After stirring for 24 h at room temperature, the mixture was concentrated in a rotary evaporator and the residue was purified by silica-gel chromatography (eluent: dichloromethane/methanol = 30:1). We obtained 3.60 g (80percent of theor.) of the target compound.LC-MS (method 1): R, = 1.79 min; MS (EIpos): m/z = 227 [M+H]+.1H-NMR (400 MHz, DMSO-D5): δ [ppm] = 8.06 (dd, IH), 8.24 (t, IH), 9.05 (d, IH), 9.07 (d, IH). |