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CAS No. : | 134168-97-1 | MDL No. : | MFCD07779529 |
Formula : | C6H5BrFN | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NGZAVSDIXFIWHJ-UHFFFAOYSA-N |
M.W : | 190.01 | Pubchem ID : | 15020155 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 38.5 |
TPSA : | 26.02 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.02 cm/s |
Log Po/w (iLOGP) : | 1.71 |
Log Po/w (XLOGP3) : | 2.03 |
Log Po/w (WLOGP) : | 2.6 |
Log Po/w (MLOGP) : | 2.67 |
Log Po/w (SILICOS-IT) : | 2.25 |
Consensus Log Po/w : | 2.25 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.79 |
Solubility : | 0.308 mg/ml ; 0.00162 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.2 |
Solubility : | 1.19 mg/ml ; 0.00625 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.17 |
Solubility : | 0.128 mg/ml ; 0.000673 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.51 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302+H312+H332-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 |
---|---|---|
75% | Stage #1: at 100℃; for 1 h; Stage #2: With sodium hydroxide In water at 20℃; |
Intermediate 180: 3-Bromo-5-fluoroanilineTo a solution of N-(3-bromo-5-fluorophenyl)acetamide (Intermediate 181, 8.7 g, 37.4 mmol) in ethanol (30 niL) was added concentrated hydrochloric acid (80 mL). The reaction was heated to 100 0C for 1 hr. It was cooled to room temperature and neutralized with 5Ν sodium hydroxide. The crude product was extracted with ethyl acetate (2x 100 mL), the combined organic layers were washed with brine, dried over magnesium sulfate, filtered, and concentrated to dryness. Chromatography on silica gel with a gradient of 5-10percent ethyl acetate in hexanes gave 5.3 g (75percent) of the product as a yellow oil.MS (ES^): 190, 192 (MH+) for C6H5BrFN 'H NMR fDMSO-D) δ 5.46 - 6.00 (m, 2H); 6.24 - 6.37 (m, IH); 6.44 - 6.53 (m, IH);6.54 - 6.61 (m, IH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | Stage #1: With hydrogenchloride; sodium nitrite In acetic acid at 0℃; for 0.333333 h; Cooling with ice Stage #2: With sodium hydrogensulfite; copper dichloride In acetic acid at 20℃; for 2.5 h; |
Intermediate S2: 3-bromo-5-fluorobenzene-1-sulfonyl chloride To a solution of 3-bromo-5-fluoroaniline (0.500 g, 2.63 mmol) in glacial acetic acid (0.70 mL) cooled in an ice bath, concentrated hydrochloric acid (2.15 mL) was added. Then, a solution of sodium nitrite (0.199 g, 2.89 mmol) in water (0.45 mL) was slowly added maintaining the temperature around 0° C. After completion of the addition, the reaction mixture was further stirred for 20 min. The resulting solution was slowly added to a freshly prepared mixture of aqueous ˜40percent sodium bisulfite solution (1.915 mL, 7.36 mmol), copper chloride (0.052 g, 0.526 mmol), glacial acetic acid (5.0 mL) and concentrated hydrochloric acid (1 mL) at room temperature and the reaction was stirred at RT for 2.5 h. The mixture was then cooled to 0° C., additional sodium nitrite (0.5 eq) was added and the stirring was continued at r.t. for 1 h. The mixture was extracted with EtOAc and the organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure to afford title compound which was used without any additional purification (0.450 g, 1.65 mmol, 63percent yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.54-7.58 (m, 1H), 7.50-7.54 (m, 1H), 7.30-7.36 (m, 1H). |