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CAS No. : | 81606-47-5 | MDL No. : | MFCD11036929 |
Formula : | C10H11BrO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PZQVCFYGWRPVLE-UHFFFAOYSA-N |
M.W : | 243.10 | Pubchem ID : | 12805128 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.3 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 55.18 |
TPSA : | 37.3 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.65 cm/s |
Log Po/w (iLOGP) : | 1.89 |
Log Po/w (XLOGP3) : | 3.01 |
Log Po/w (WLOGP) : | 2.81 |
Log Po/w (MLOGP) : | 2.99 |
Log Po/w (SILICOS-IT) : | 2.59 |
Consensus Log Po/w : | 2.66 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -3.45 |
Solubility : | 0.0857 mg/ml ; 0.000352 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.46 |
Solubility : | 0.0847 mg/ml ; 0.000348 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.45 |
Solubility : | 0.0859 mg/ml ; 0.000353 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.74 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
91% | Stage #1: With lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at 0℃; for 1.25 h; Stage #2: for 15.1667 h; Stage #3: With hydrogenchloride; water In tetrahydrofuran; n-heptane; ethylbenzene |
Step 2: To a solution of lithium diisopropylamide in tetrahydrofuran/n-heptane/ethylbenzene (1.8 M, 17 mL) at 0° C. is added a solution of 2-(3-bromo-phenyl)-propionic acid (3 g, 13.9 mmol) in tetrahydrofuran (5 mL) dropwise during 15 minutes. The mixture is stirred for 1 hour, followed by addition of methyl iodide (4.93 g, 34.8 mmol) in tetrahydrofuran (5 mL) dropwise during 10 min. The reaction mixture is stirred for 15 hours, quenched with 2 N HCl, concentrated in vacuo, and diluted with ether (150 mL). The ether layer is washed with 2 N HCl, extracted three times with 2 N NaOH (50 mL). The combined NaOH layers are acidified with 6 N HCl to pH=1 and extracted three times with ether (75 mL). The combined organic layers are washed with brine, dried over sodium sulfate and concentrated to obtain 2-(3-bromo-phenyl)-2-methyl-propionic acid as a solid (3.08 g, 91percent), which is used without further purification. LC/MS: 243 (M+H). |
91% | Stage #1: With lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at 0℃; for 1.25 h; Stage #2: for 15.1667 h; |
To a solution of LDA in THF/n-heptane/ethylbenzene (1.8 M, 17 mL) at O0C is added a solution of 2-(3-bromo-phenyl)-propionic acid [3 g, 13.9 mmol, Intermediate (69)] in THF (5 mL) dropwise during 15 minutes. Stir for 1 hour, followed by addition of methyl iodide (4.93 g, 34.8 mmol) in THF (5 mL) dropwise during 10 min. The reaction mixture is stirred for 15 hours, quenched with 2N hydrochloric acid, concentrated in vacuo, and diluted with ether (150 mL). The ether layer is washed with 2N hydrochloric acid, extracted three times with 2N sodium hydroxide (50 mL), Combined sodium hydroxide layers are acidified with 6 N hydrochloric acid to pH=l and extracted three times with ether (75 mL). Combined organic layers are washed with brine, dried over sodium <n="174"/>sulfate and concentrated to obtain 2-(3-bromo-phenyl)-2-methyl-propionic acid as a solid (3.08 g, 91percent yield), which is used without further purification. LC/MS: 243 (M+H) |
91% | Stage #1: With lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at 0℃; for 1.25 h; Stage #2: for 15.1667 h; |
To a solution of LDA in THF/n-heptane/ethylbenzene (1.8 M, 17 mL) at O0C is added a solution of 2-(3-bromo-phenyl)-propionic acid [3 g, 13.9 mmol, Intermediate (69)] in THF (5 mL) dropwise during 15 minutes. Stir for 1 hour, followed by addition of methyl iodide (4.93 g, 34.8 mmol) in THF (5 mL) dropwise during 10 min. The reaction mixture is stirred for 15 hours, quenched with 2N hydrochloric acid, concentrated in vacuo, and diluted with ether (150 mL). The ether layer is washed with 2N hydrochloric acid, extracted three times with 2N sodium hydroxide (50 mL), Combined sodium hydroxide layers are acidified with 6 N hydrochloric acid to pH=l and extracted three times with ether (75 mL). Combined organic layers are washed with brine, dried over sodium <n="174"/>sulfate and concentrated to obtain 2-(3-bromo-phenyl)-2-methyl-propionic acid as a solid (3.08 g, 91percent yield), which is used without further purification. LC/MS: 243 (M+H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | Stage #1: With lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at 0℃; for 1.25 h; Stage #2: for 15 h; |
b) Step 1. To a solution of LDA in THF/n-heptane/ethylbenzene (1.8 M, 17 mL) at 0°C is added a solution of 2-(3-bromo-phenyl)-propionic acid [3 g, 13.9 mmol, Intermediate (69)] in THF (5 mL) dropwise during 15 minutes. Stir for 1 hour, followed by addition of methyl iodide (4.93 g, 34.8 mmol) in THF (5 mL) dropwise during 10 min. The reaction mixture is stirred for 15 hours, quenched with 2N hydrochloric acid, concentrated in vacuo, and diluted with ether (150 mL). The ether layer is washed with 2N hydrochloric acid, extracted three times with 2N sodium hydroxide (50 mL), Combined sodium hydroxide layers are acidified with 6 N hydrochloric acid to pH=l and extracted three times with ether (75 mL). Combined organic layers are washed with brine, dried over sodium sulfate and concentrated to obtain 2-(3 -bromo-phenyl)-2-methyl-propionic acid as a solid (3.08 g, 91percent yield), which is used without further purification. LC/MS: 243 (M+H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | Stage #1: With methanol; sodium hydroxide In tetrahydrofuran for 2 h; Reflux Stage #2: With hydrogenchloride In water |
INTERMEDIATE 82-(3 -Bromophenyl)-2-methylpropionic acidSodium hydroxide (2M, 20 mL) was added to a solution of Intermediate 7 (6.5 g) in MeOH (20 mL) and THF (20 mL). The resulting mixture was refluxed for 2 h. The mixture was evaporated, and the residue partitioned between water and DCM (100 mL each). The aqueous phase was acidified (2M hydrochloric acid) and extracted with DCM (100 mL then 50 mL). The combined organic phases were dried (MgSO4) and the solvent removed in vacuo to give the title compound (4.55 g, 68percent over two steps) as a cream solid. δH (CDCl3) 7.54 (s, IH), 7.40 (d, IH), 7.33 (d, IH), 7.21 (t, IH), 1.59 (s, 6H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | Stage #1: Heating / reflux Stage #2: With hydrogenchloride In water |
A6.1c: 2-(3-bromophenyl)-2-methylpropanoic acid; To a solution of A6.1b (22 g, 0.081 mol) in ethanol (220 ml) was added sodium hydroxide (9.7 g, 0.405 mol) and heated to reflux over night. The reaction mixture was concentrated to remove ethanol. The crude product was dissolved in water (200 ml) and washed with ether (2.x.150 ml). The aqueous later was acidified with 6N HCl and extracted with ethyl acetate. Combined organic layer was washed with water, brine, dried over anhydrous sodium sulfate and concentrated to give 17 g (86percent) of A6.1c as white solid. 1H NMR (300 MHz, CDCl3) 1.6 (s, 6H), 7.27 (dd, 1H), 7.35 (d, 1H), 7.4 (d, 1H), 7.55 (s, 1H). |
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