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CAS No. : | 33842-18-1 | MDL No. : | MFCD23701705 |
Formula : | C9H7BrO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LCYYWZCNOLIBQE-UHFFFAOYSA-N |
M.W : | 259.05 g/mol | Pubchem ID : | 71463973 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.22 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 51.48 |
TPSA : | 44.76 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) : | -6.26 cm/s |
Log Po/w (iLOGP) : | 2.47 |
Log Po/w (XLOGP3) : | 2.28 |
Log Po/w (WLOGP) : | 1.96 |
Log Po/w (MLOGP) : | 1.79 |
Log Po/w (SILICOS-IT) : | 2.4 |
Consensus Log Po/w : | 2.18 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.07 |
Solubility : | 0.222 mg/ml ; 0.000856 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.86 |
Solubility : | 0.36 mg/ml ; 0.00139 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.08 |
Solubility : | 0.214 mg/ml ; 0.000828 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.47 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
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* 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 |
---|---|---|
Rk. mit Cu(I)CN; | ||
Rk. mit HNO3; | ||
Hydrierung; |
Umsetzung mit Cu(I)CN, sowie HNO3 u. Hydrierung ?; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(1b), Brom in H2O/CHCl3; | ||
aus (1b), Brom in H2O/ CHCl3; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: thionyl chloride / 0 °C / Reflux; Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: bromine; acetic acid / 12 h / 20 °C 2: thionyl chloride / 0 °C / Reflux; Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; | Dibromomethane (3.2 mL, 45.3 mmol) was added dropwise into a mixture of the compound (17-2) (7.5 g, 30.2 mmol) obtained in Step 102 2 of Example 17 in 30 DMF (100 mL) as well as 67 K2CO3 (12.5 g, 95.0 mmol). A reaction mixture was heated at 100C overnight, after which a reaction thereof was completed with water. A water layer was extracted with EtOAc, after which a combined organic layer was washed with brine, such that the resulting product was dried over anhydrous MgSO4, filtered and concentrated under vacuum. A resulting residue was purified by means of a silica gel column chromatography, so as to obtain the 127 title compound (19-1) (7.6 g, 29.3 mmol, 97%). (0166) 1H NMR (400 MHz, CDCl3); delta 7.55 (d, J = 2.0 Hz, 1H), 7.08 (d, J = 1.6 Hz, 1H), 6.12 (s, 2H), 3.92 (s, 3H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With water; sodium hydroxide In tetrahydrofuran; methanol at 20℃; for 4h; | 19.2 Step 2. Synthesis of 6-bromobenzo[d][1,3]dioxol-4-carboxylic acid (19-2) A 1N-NaOH aqueous solution (58.7 mL) was added into the compound (19-1) (7.6 g, 29.3 mmol) in THF/MeOH (40 mL/80 mL) at room temperature. A reaction mixture was stirred at room temperature for 4 hours. After a reaction was completed, a volatile substance was removed under reduced pressure. A 1N-HCl aqueous solution was added into a residue to carry out acidification, during which a resulting mixture was stirred to precipitate a crude product. The crude product was filtered, washed with water and dried under high vacuum, so as to obtain the title compound (19-2) (7.2 g, 29.3 mmol, 99%). (0169) 1H NMR (400 MHz, CDCl3); δ 7.59 (d, J = 2.0 Hz, 1H), 7.13 (d, J = 2.0 Hz, 1H), 6.16 (s, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: potassium fluoride / N,N-dimethyl-formamide / 0.5 h 1.2: 30 h / 110 °C 2.1: acetic acid; sodium acetate; bromine / 12 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With bromine; sodium acetate; acetic acid at 20℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | With copper(l) iodide; ammonia; caesium carbonate In N,N-dimethyl-formamide; acetylacetone at 70℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: caesium carbonate; copper(l) iodide; ammonia / N,N-dimethyl-formamide; acetylacetone / 12 h / 70 °C 2: lithium hydroxide / methanol; water / 4 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
17% | Stage #1: methyl 6-bromobenzo[d][1,3]dioxole-4-carboxylate With lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at -78℃; for 0.25h; Stage #2: methyl iodide In tetrahydrofuran; n-heptane; ethylbenzene at 20℃; for 1.5h; | 2 Methyl 6-bromo-7-methylbenzo[d][1,3]dioxole-4-carboxylate. To a solution of lithium diisopropyl amide (0.32 mL, 0.64 mmol, 1.1 eq, 2.0 M solution in THF/heptane/ethylbenzene) in THF (2 mL) at -78 °C was added methyl 6- bromobenzo[d][l,3]dioxole-4-carboxylate (150 mg, 0.58 mmol, 1 eq) dissolved in THF (1 mL) dropwise. The resulting solution was stirred at -78 °C for 15 min, after which time methyl iodide (0.11 mL, 1.74 mmol, 3 eq) was added dropwise. The resulting solution was slowly warmed to r.t. over 30 min, and stirred for 1 h at r.t. The reaction mixture was quenched with H2O, and diluted with DCM. 1M HC1 was then added, and the aqueous layer was extracted with DCM. The combined organic extracts were filtered through a phase separator and concentrated, and the crude residue was purified by column chromatography (3-50% EtOAc in hexanes) to give the title compound as a white solid (27 mg, 17%). 1H-NMR (400 MHz, CDCl3) d 7.61 (s, 1H), 6.11 (s, 2H), 3.90 (s, 3H), 2.27 (s, 3H). ES-MS [M+H]+ = 273.2, 275.2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / dimethyl sulfoxide / 0.17 h / 120 °C / Microwave irradiation; Sealed tube; Inert atmosphere 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate / 1,4-dioxane; water / 2 h / 90 °C / Sealed tube; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / dimethyl sulfoxide / 0.17 h / 120 °C / Microwave irradiation; Sealed tube; Inert atmosphere 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate / 1,4-dioxane; water / 2 h / 90 °C / Sealed tube; Inert atmosphere 3: lithium hydroxide / water; tetrahydrofuran; methanol / 1.5 h / 20 - 35 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / dimethyl sulfoxide / 0.17 h / 120 °C / Microwave irradiation; Sealed tube; Inert atmosphere 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate / 1,4-dioxane; water / 2 h / 90 °C / Sealed tube; Inert atmosphere 3: lithium hydroxide / water; tetrahydrofuran; methanol / 1.5 h / 20 - 35 °C 4: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane; ethylbenzene / 0.25 h / -78 °C 1.2: 1.5 h / 20 °C 2.1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 0.5 h / 120 °C / Microwave irradiation; Sealed tube; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane; ethylbenzene / 0.25 h / -78 °C 1.2: 1.5 h / 20 °C 2.1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 0.5 h / 120 °C / Microwave irradiation; Sealed tube; Inert atmosphere 3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate / 1,4-dioxane; water / 1 h / 90 °C / Sealed tube; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane; ethylbenzene / 0.25 h / -78 °C 1.2: 1.5 h / 20 °C 2.1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 0.5 h / 120 °C / Microwave irradiation; Sealed tube; Inert atmosphere 3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate / 1,4-dioxane; water / 1 h / 90 °C / Sealed tube; Inert atmosphere 4.1: lithium hydroxide / water; tetrahydrofuran / 3 h / 40 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane; ethylbenzene / 0.25 h / -78 °C 1.2: 1.5 h / 20 °C 2.1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 0.5 h / 120 °C / Microwave irradiation; Sealed tube; Inert atmosphere 3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate / 1,4-dioxane; water / 1 h / 90 °C / Sealed tube; Inert atmosphere 4.1: lithium hydroxide / water; tetrahydrofuran / 3 h / 40 °C 5.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In dimethyl sulfoxide at 120℃; for 0.166667h; Microwave irradiation; Sealed tube; Inert atmosphere; | 1 Methyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d][1,3]dioxole-4-carboxylate Methyl 6-bromobenzo[d][l,3]dioxole-4-carboxylate (250 mg, 0.97 mmol, 1 eq), bis(pinacolato)diboron (294 mg, 1.16 mmol, 1.2 eq), potassium acetate (284 mg, 2.90 mmol, 3 eq) and Pd(dppf)Cl2*DCM (24 mg, 0.029 mmol, 0.03 eq) were combined in a microwave vial which was sealed and placed under an inert atmosphere. DMSO (4.5 mL) was then added via syringe, and the resulting mixture was heated with microwave irradiation at 120 °C for 10 min, after which time the reaction mixture was diluted with EtOAc and H2O, and the aqueous layer was extracted with EtOAc. The combined organic extracts were dried with MgS04, and solvents were filtered and concentrated to give the title compound as a brown oil which was used directly without further purification. (295 mg, 100%). ES-MS [M+H]+ = 307.3. |
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