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CAS No. : | 107224-21-5 | MDL No. : | MFCD22688808 |
Formula : | C9H5BrFN | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BEKXRHNEJQGHMH-UHFFFAOYSA-N |
M.W : | 226.05 | Pubchem ID : | 13792203 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 49.4 |
TPSA : | 12.89 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) : | -5.76 cm/s |
Log Po/w (iLOGP) : | 2.14 |
Log Po/w (XLOGP3) : | 2.7 |
Log Po/w (WLOGP) : | 3.56 |
Log Po/w (MLOGP) : | 2.98 |
Log Po/w (SILICOS-IT) : | 3.54 |
Consensus Log Po/w : | 2.98 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.56 |
Solubility : | 0.0624 mg/ml ; 0.000276 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.62 |
Solubility : | 0.538 mg/ml ; 0.00238 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.84 |
Solubility : | 0.00327 mg/ml ; 0.0000145 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.68 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312+P330-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P362-P403+P233-P405-P501 | 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 |
---|---|---|
15% | With sulfuric acid; In nitrobenzene; at 0 - 150℃; for 5.4h; | [0285] A solution of <strong>[656-64-4]3-bromo-4-fluoroaniline</strong> (20 g, 105.2 mmol) and glycerol (20.1 mL, 263.1 mmol) in nitrobenzene (10.8 mL, 105.2 mmol) was cooled to 0 C, and cone. H2S04 (48 mL, 2.4 vol per g) was added slowly over a period of 24 min. The reaction temperature was gradually increased to 150 C and the reaction mixture was stirred at 150 C for 5 hrs. Then the reaction mixture was allowed to cool down to r.t., poured into crushed ice, and extracted with Ethyl Acetate (3 x 500 mL). Combined organic layers were washed with water (300 mL), brine (300 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resultant crude compound was purified by column chromatography (100-200 silica) using 20% Ethyl Acetate in Hexane as eluent to afford 14 g (59% yield) isomeric mixture of 7-bromo-6-fluoroquinoline Int-6 and 8-bromo-7-fluoroquinoline Int-6A as a brown solid. The isomeric mixture of compound Int-6 and Int-6A (14 g) was separated by prep-HPLC purification to afford 3.6 g (15% yield) of compound Int-6. MS (ESI) m/z 227.95 [M+H]+. |
With sulfuric acid; sodium 3-nitrobenzenesulfonate; In water; at 150℃; for 2h; | Water (11.38 mL) was added to a solution consisting of <strong>[656-64-4]3-bromo-4-fluoroaniline</strong> (10 g, 53 mmol), sodium 3-nitrobenzenesulfonate (21 g, 95 mmol), and propane-1,2,3-triol (14 g, 0.15 mol). The resultant mixture was carefully treated with concentrated H2SO4 (21.1 mL), and then heated to 150 C. with stirring for 2 h before cooling to room temperature. The resultant mixture was carefully neutralized with 5 N sodium hydroxide, filtered through a pad of diatomaceous earth, and the pad was washed with dichloromethane (50 mL). The resultant mixture was extracted with dichloromethane (100 mL*3) and the combined organic extracts were dried over Na2SO4, filtered, and the filtrate concentrated to give a crude product, which was purified by FCC (petroleum ether: ethyl acetate=3:1) to afford the compounds 62a and 62a-1 (9.5 g, 80%). LCMS (ESI): RT=0.64, 0.68 min, mass calcd. for C9H5BrFN 224.96, m/z found 227.6 [M+H]+. 1H NMR (400 MHz, CDCl3) delta 8.96-8.87 (m, 2H), 8.55 (d, J=8.8 Hz, 1H), 8.39 (d, J=6.8 Hz, 1H), 8.15-8.07 (m, 2H), 7.60-7.42 (m, 4H). |