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CAS No. : | 1256795-14-8 | MDL No. : | MFCD18260465 |
Formula : | C10H8BrN | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BQFFOKXBGUHZLJ-UHFFFAOYSA-N |
M.W : | 222.08 | Pubchem ID : | 121226474 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.1 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 54.41 |
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) : | -5.35 cm/s |
Log Po/w (iLOGP) : | 2.26 |
Log Po/w (XLOGP3) : | 3.25 |
Log Po/w (WLOGP) : | 3.31 |
Log Po/w (MLOGP) : | 2.85 |
Log Po/w (SILICOS-IT) : | 3.6 |
Consensus Log Po/w : | 3.05 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.88 |
Solubility : | 0.0292 mg/ml ; 0.000132 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.19 |
Solubility : | 0.142 mg/ml ; 0.000639 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.95 |
Solubility : | 0.00251 mg/ml ; 0.0000113 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.24 |
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 |
---|---|---|
25%; 20% | With sulfuric acid; sodium 3-nitrobenzenesulfonate; In water; at 120 - 130℃; for 1.5h; | The raw materials 3,5-difluoroaniline G-1 (5.6 g, 27 mmol) and sodium 3-nitrobenzenesulfonate (7.2 g, 32 mmol) Was added to a mixed solution of concentrated sulfuric acid (15 mL) and water (6 mL) After heating to an internal temperature of 120 C, glycerol (7.4 g, 80 mmol) After the addition was completed, the temperature was raised to 130 C and reacted for 1.5h, then cooled. The reaction was poured into crushed ice, concentrated ammonia water to adjust the pH to 5 ~ 6, the precipitated solid was filtered off, washed with water, After drying, column chromatography gave 3.82 g of white solid compound G-2 in 58% yield. A mixture of 6-bromo-7-methylquinoline (I-2) and 6-bromo-5-methylquinoline (J-1) was synthesized. Then separated by supercritical preparative chromatography (SFC), IC-H column, mobile phase: isopropanol / carbon dioxide = 18/82, detection wavelength: 254nm. The first fraction was collected as 6-bromo-7-methylquinoline (I-2) as a white solid, yield: 25%. The second fraction was collected as a 6-bromo-5-methylquinoline (J-1) white solid in a yield of 20% |
With sulfuric acid; sodium 3-nitrobenzenesulfonate; In water; at 110 - 140℃; | General procedure: 4-Bromo-3-fluoroaniline (D-1, 5.0 g, 26.3 mmol) and sodium 3-nitrobenzenesulfonate (7.1 g, 31.6 mmol)were added to the mixture of H2SO4 (20ml) and H2O (10ml). When the mixture was heated to 110C, Glycerin (7.27 g,78.9 mmol) was added slowly, then the reactionwas stirred at 140C overnight. After cooled to rt, the mixture was poured to alarge amount of ice water, concentrated ammonia water was added to adjust topH=8, then extracted with EtOAc, washed with brine and dried over anhydrous Na2SO4,then purified by flash column chromatography to afford6-bromo-7-fluoroquinoline as white solid (D-2,4.8 g, 81% yield). LC-MS (ESI): [M+H]+=226. 1H NMR (400MHz, CDCl3) delta 8.93 (dd, J1=4.4Hz, J2=1.6 Hz, 1H),8.12-8.02 (m, 2H), 7.81 (d, J=9.6 Hz, 1H), 7.41 (dd, J1=8.4 Hz, J2=4.4 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 4 h / 110 °C 2: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C 3: phosphorus tribromide / chloroform / 2 h / 0 °C / Reflux 4: potassium iodide / N,N-dimethyl-formamide / 2 h / 120 °C 5: hydrazine hydrate / ethanol / 2 h / Reflux 6: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 12 h / 180 °C / Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 4 h / 110 °C 2: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C 3: phosphorus tribromide / chloroform / 2 h / 0 °C / Reflux 4: potassium iodide / N,N-dimethyl-formamide / 2 h / 120 °C 5: hydrazine hydrate / ethanol / 2 h / Reflux 6: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 12 h / 180 °C / Sealed tube 7: 12 h / 150 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 4 h / 110 °C 2: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 4 h / 110 °C 2: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C 3: phosphorus tribromide / chloroform / 2 h / 0 °C / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 4 h / 110 °C 2: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C 3: phosphorus tribromide / chloroform / 2 h / 0 °C / Reflux 4: potassium iodide / N,N-dimethyl-formamide / 2 h / 120 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1: bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 4 h / 110 °C 2: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C 3: phosphorus tribromide / chloroform / 2 h / 0 °C / Reflux 4: potassium iodide / N,N-dimethyl-formamide / 2 h / 120 °C 5: hydrazine hydrate / ethanol / 2 h / Reflux 6: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 12 h / 180 °C / Sealed tube 7: 12 h / 150 °C 8: 1,1'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex; potassium carbonate / water; 1,4-dioxane / 4 h / 110 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1: bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 4 h / 110 °C 2: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C 3: phosphorus tribromide / chloroform / 2 h / 0 °C / Reflux 4: potassium iodide / N,N-dimethyl-formamide / 2 h / 120 °C 5: hydrazine hydrate / ethanol / 2 h / Reflux 6: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 12 h / 180 °C / Sealed tube 7: 12 h / 150 °C 8: 1,1'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex; potassium carbonate / water; 1,4-dioxane / 4 h / 110 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1: bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 4 h / 110 °C 2: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C 3: phosphorus tribromide / chloroform / 2 h / 0 °C / Reflux 4: potassium iodide / N,N-dimethyl-formamide / 2 h / 120 °C 5: hydrazine hydrate / ethanol / 2 h / Reflux 6: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 12 h / 180 °C / Sealed tube 7: 12 h / 150 °C 8: 1,1'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex; potassium carbonate / water; 1,4-dioxane / 4 h / 110 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1: bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 4 h / 110 °C 2: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C 3: phosphorus tribromide / chloroform / 2 h / 0 °C / Reflux 4: potassium iodide / N,N-dimethyl-formamide / 2 h / 120 °C 5: hydrazine hydrate / ethanol / 2 h / Reflux 6: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 12 h / 180 °C / Sealed tube 7: 12 h / 150 °C 8: 1,1'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex; potassium carbonate / water; 1,4-dioxane / 4 h / 110 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1: bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 4 h / 110 °C 2: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C 3: phosphorus tribromide / chloroform / 2 h / 0 °C / Reflux 4: potassium iodide / N,N-dimethyl-formamide / 2 h / 120 °C 5: hydrazine hydrate / ethanol / 2 h / Reflux 6: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 12 h / 180 °C / Sealed tube 7: 12 h / 150 °C 8: 1,1'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex; potassium carbonate / water; 1,4-dioxane / 4 h / 110 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1: bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 4 h / 110 °C 2: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C 3: phosphorus tribromide / chloroform / 2 h / 0 °C / Reflux 4: potassium iodide / N,N-dimethyl-formamide / 2 h / 120 °C 5: hydrazine hydrate / ethanol / 2 h / Reflux 6: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 12 h / 180 °C / Sealed tube 7: 12 h / 150 °C 8: 1,1'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex; potassium carbonate / water; 1,4-dioxane / 4 h / 110 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 4 h / 110 °C 2: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C 3: phosphorus tribromide / chloroform / 2 h / 0 °C / Reflux 4: potassium iodide / N,N-dimethyl-formamide / 2 h / 120 °C 5: hydrazine hydrate / ethanol / 2 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bis-triphenylphosphine-palladium(II) chloride In 1,4-dioxane at 110℃; for 4h; | General procedure: D-2(2.1 g, 9.3 mmol), 1-ethoxyvinyltri-n-butyltin (3.6 g, 10.1 mmol) and Pd(PPh3)2Cl2(0.3 g, 0.5 mmol) were added to dioxane (20 ml), the mixture was stirred at 110Cfor 4h. After cooled to rt, KF (2.0 g, 21.3 mmol) and water (4 ml) were added,then stirred at rt for 2 h, filtrated and washed with dioxane (5 ml×3). Conc. HCl (2 ml) was added to themother liquor and stirred at rt for 1 h. Then concentrated and added saturatedNa2CO3 aqueous (50 ml), extracted with EtOAc, washed withbrine and dried over anhydrous Na2SO4, then purified byflash column chromatography to afford 1-(7-fluoroquinolin-6-yl)ethan-1-one aspale white solid (D-3, 1.5 g, 87%yield). LC-MS (ESI): [M+H]+=190. 1H NMR (400 MHz, CDCl3)δ 8.99 (dd, J1=4.4 Hz, J2=1.6 Hz, 1H), 8.41 (d, J=8.0Hz, 1H), 8.26 (dd, J1=8.4Hz, J2=1.2 Hz, 1H), 7.81(d, J=12.0 Hz, 1H), 7.44 (dd, J1=8.4Hz, J2=4.4 Hz, 1H), 2.76(d, J=4.8 Hz, 3H). |
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