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CAS No. : | 1126824-44-9 | MDL No. : | MFCD11878499 |
Formula : | C10H8BrNO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OXTZDFDSYUFWNS-UHFFFAOYSA-N |
M.W : | 238.08 | Pubchem ID : | 71238226 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.1 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 55.94 |
TPSA : | 22.12 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) : | -5.73 cm/s |
Log Po/w (iLOGP) : | 2.43 |
Log Po/w (XLOGP3) : | 2.85 |
Log Po/w (WLOGP) : | 3.01 |
Log Po/w (MLOGP) : | 2.19 |
Log Po/w (SILICOS-IT) : | 3.1 |
Consensus Log Po/w : | 2.72 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.61 |
Solubility : | 0.0578 mg/ml ; 0.000243 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.97 |
Solubility : | 0.253 mg/ml ; 0.00106 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.69 |
Solubility : | 0.00489 mg/ml ; 0.0000206 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.73 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H320-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 |
---|---|---|
27% | Step 1 : 4.0g (0.02 mol) of 3-Bromo-5-methoxy-aniline, 4.6 g (0.05 mol) of glycerol, 2.46g (0.02 mol) of nitrobenzene and 12 ml of 75percent sulfuric acid were stirred for 3 h at 150°C. After this dark solution was poured onto 100 g of crushed ice, 100 ml of ethylacetate (EtOAc) and 30 ml of 30percent solution of NaOH. After 1 hour brown solid was filtered off and the organic layer was separated. After filtering through Si02 and evaporation of solvent 7-bromo-5- methoxy-quinoline and 5-bromo-7-methoxy-quinoline were separated as mixture approximately 60:40 (total 3.5g, 74percent) This mixture was separated to individual 7-bromo-5- methoxy-quinoline and 5-bromo-7-methoxy-quinoline with column chromatography on silica-gel with benzene-EtOAc (3: 1) as eluent. Yield of pure 7-bromo-5-methoxy-quinoline was 950 mg (27percent from mixture). | |
950 mg | With sulfuric acid; In water; nitrobenzene; at 150℃; for 3.0h; | 4.1.2. Synthesis of 5-hydroxy-7-bromo-quinoline from Scheme 2[0119]The title compound can be purchased by Shanghai Haoyuan Chemexpress Co., Ltd. CHINA or synthesized via known <strong>[16618-68-1]3-bromo-5-methoxyaniline</strong> (Liedholm, Brita. Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry (1984), B38(10), 877-84 or Hodgson, H. H.; Wignall, J. S Journal of the Chemical Society (1926)) in two steps. 3-Bromo-5-methoxy-aniline, 4.6 g (0.05 mol) of glycerol, 2.46 g (0.02 mol) of nitrobenzene and 12 ml of 75percent sulfuric acid were stirred for 3 h at 150???° C. After this dark solution was poured onto 100 g of crushed ice, 100 ml of ethylacetate (EtOAc) and 30 ml of 30percent solution of NaOH. After 1 hour brown solid was filtered off and the organic layer was separated. After filtering through SiO2 and evaporation of solvent 7-bromo-5-methoxy-quinoline and 5-bromo-7-methoxy-quinoline were separated as mixture approximately 60:40 (total 3.5 g, 74percent) This mixture was separated to individual 7-bromo-5-methoxy-quinoline and 5-bromo-7-methoxy-quinoline with column chromatography on silica-gel with benzene-EtOAc (3:1) as eluent. Yield of pure 7-bromo-5-methoxy-quinoline was 950 mg (27percent from mixture). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
7-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline A solution of <strong>[1126824-44-9]5-bromo-7-methoxyquinoline</strong> (0.407 g, 1.71 mmol, OxChem, Wood Dale, Ill., USA), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (0.912 g, 3.59 mmol), PdCl2(dppf) (0.051 g, 0.070 mmol), and potassium acetate (0.503 g, 5.13 mmol) in DMF (9 mL) was stirred at 90° C. for 1 h then at 100° C. for 45 min. The reaction mixture was diluted with EtOAc (100 mL), and washed with saturated, aqueous sodium bicarbonate (2*75 mL). The organic layer was separated, dried over anhydrous Na2SO4, and concentrated in vacuo. The crude product was adsorbed onto silica and purified via column chromatography (silica gel, 0-80percent heptane/EtOAc) to give 7-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline. MS (ESI, +ve) m/z: 286.1 (M+1)+. | ||
With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate; In N,N-dimethyl-formamide; at 90 - 100℃; for 1.75h; | A solution of <strong>[1126824-44-9]5-bromo-7-methoxyquinoline</strong> (0.407 g, 1.71 mmol, OxChem, Wood Dale, IL, USA), 4,4,4?,4?,5,5,5?,5?-octamethyl-2,2?-bi(1 ,3,2-dioxaborolane) (0.912 g, 3.59 mmol), PdC12(dppf) (0.05 1 g, 0.070 mmol), and potassium acetate (0.503 g, 5.13 mmol) in DMF (9 mL) was stirred at 90 °C for 1 h then at 100 °C for 45 mm. The reaction mixture was diluted with EtOAc (100 mL), and washed with saturated, aqueous sodium bicarbonate (2 x 75 mL). The organic layer was separated, dried over anhydrous Na2504, and concentrated in vacuo. The crude product was adsorbed onto silica and purified via column chromatography (silica gel, 0?80percent heptane/EtOAc) to give 7-methoxy-5-(4,4,5,5 -tetramethyl- 1 ,3,2-dioxaborolan-2- yl)quinoline. MS (ESI, +ve) m/z: 286.1 (M + 1). | |
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In N,N-dimethyl-formamide; at 90 - 100℃; for 1.75h; | 7-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline A solution of <strong>[1126824-44-9]5-bromo-7-methoxyquinoline</strong> (0.407 g, 1.71 mmol, OxChem, Wood Dale, Ill., USA), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (0.912 g, 3.59 mmol), PdCl2(dppf) (0.051 g, 0.070 mmol), and potassium acetate (0.503 g, 5.13 mmol) in DMF (9 mL) was stirred at 90° C. for 1 h then at 100° C. for 45 min. The reaction mixture was diluted with EtOAc (100 mL), and washed with saturated, aqueous sodium bicarbonate (2*75 mL). The organic layer was separated, dried over anhydrous Na2SO4, and concentrated in vacuo. The crude product was adsorbed onto silica and purified via column chromatography (silica gel, 0-80percent heptane/EtOAc) to give 7-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline. MS (ESI, +ve) m/z: 286.1 (M+1)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
4.4 g; 20.6 g | In methanol; N,N-dimethyl-formamide; at 60℃; for 2h; | Add <strong>[34522-69-5]5,7-dibromoquinoline</strong> (40.0 g, 0.139 mol),Methanol (300 mL) and DMF (200 mL), warm up to 60C, then add sodium methoxide (65.5 g, 1.21 mol) to react for 2 h,The reaction solution was poured into water, fully extracted with ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, spin-dried, concentrated, and purified by column chromatography (eluent: V (petroleum ether): V (ethyl acetate)) =20:1), the compounds 5-bromo-7-methoxyquinoline (20.6 g) and 7-bromo-5-methoxyquinoline (4.4 g) were obtained, and the total yield was 75%. |