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CAS No. : | 22090-26-2 | MDL No. : | MFCD04112480 |
Formula : | C10H12BrN | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BVEGBJXZICCEQW-UHFFFAOYSA-N |
M.W : | 226.11 | Pubchem ID : | 7016457 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.4 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 58.78 |
TPSA : | 3.24 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -4.66 cm/s |
Log Po/w (iLOGP) : | 2.58 |
Log Po/w (XLOGP3) : | 4.25 |
Log Po/w (WLOGP) : | 2.67 |
Log Po/w (MLOGP) : | 3.07 |
Log Po/w (SILICOS-IT) : | 3.02 |
Consensus Log Po/w : | 3.12 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.22 |
Solubility : | 0.0135 mg/ml ; 0.0000598 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -4.03 |
Solubility : | 0.0211 mg/ml ; 0.0000934 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -3.7 |
Solubility : | 0.0449 mg/ml ; 0.000199 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 1.27 |
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 |
---|---|---|
46% | With caesium carbonate In N,N-dimethyl-formamide at 60℃; | Step 82a: l-(4-Bromophenyl)pyrrolidine (Compound 0601-155)A mixture of 4-bromoaniline (1 g, 5.81 mmol), Cs2C03 (5.68 g, 17.44 mmol), 1,4- dibromobutane (1.88 g, 8.72 mmol) in DMF (20 mL) was stirred at 60 °C overnight. After cooled to room temperature, the mixture was diluted with water (200 mL) and extracted with ethyl acetate (2 x 100 mL). The organic layer was washed with water (3 x 100 mL) and brine (100 mL), dried over Na2S04, concentrated and purified by columnchromatography on silica gel (petroleum ether) to give compound 0601-155 (720 mg, 46percent) as a colorless oil. LCMS: 226 [M+l]+. 1H NMR (400 MHz, DMSO-<3/4) δ 1.94 (t, J= 6.4 Hz, 4H), 3.18 (t, J= 6.4 Hz, 4H), 6.47 (d, J= 9.2 Hz, 1H), 7.27 (d, J= 9.2 Hz, 1H). |
46% | With caesium carbonate In N,N-dimethyl-formamide at 60℃; | Step 82a: 1-(4-Bromophenyl)pyrrolidine (Compound 0601-155)[0550]A mixture of 4-bromoaniline (1 g, 5.81 mmol), Cs2CO3 (5.68 g, 17.44 mmol), 1,4-dibromobutane (1.88 g, 8.72 mmol) in DMF (20 mL) was stirred at 60° C. overnight. After cooled to room temperature, the mixture was diluted with water (200 mL) and extracted with ethyl acetate (2×100 mL). The organic layer was washed with water (3×100 mL) and brine (100 mL), dried over Na2SO4, concentrated and purified by column chromatography on silica gel (petroleum ether) to give compound 0601-155 (720 mg, 46percent) as a colorless oil. LCMS: 226 [M+1]+. 1H NMR (400 MHz, DMSO-d6) δ 1.94 (t, J=6.4 Hz, 4H), 3.18 (t, J=6.4 Hz, 4H), 6.47 (d, J=9.2 Hz, 1H), 7.27 (d, J=9.2 Hz, 1H). |
46% | With caesium carbonate In N,N-dimethyl-formamide at 60℃; | DMF (20mL) in, 4-bromo-aniline (1g, 5.81mmol), Cs2CO3 (5.68g, 17.44mmol), 1,4- dibromobutane (1.88g, 8.72mmol) was stirred overnight in a mixture of 60 of, after cooling to room temperature, the mixture was diluted with water (200mL), and extracted with ethyl acetate (2x100mL). The organic layer was washed with water (3 × 100 mL) and brine (100 mL), dried over Na2SO4, and purified by column chromatography on silica gel (petroleum ether) and concentrated to give the compound 0601-155 as a colorless oil It was (720mg, 46percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86%. | With N-Bromosuccinimide In tetrahydrofuran at 20 - 30℃; for 4 h; | Reference Example 5 N-(4-bromophenyl)pyrrolidine To a solution of N-phenylpyrrolidine (73.8 g, 0.501 moL) in tetrahydrofuran (500 mL) was added N-bromosuccinimide (124.8 g, 1.4 equivalents) at 20°C to 30°C, and the mixture was stirred at the same temperature for 4 hr. 1 mol/L Aqueous sodium hydroxide solution (300 mL) was added to the mixture at 27°C, and the mixture was partitioned. The organic layer was dried over anhydrous magnesium sulfate and filtered naturally, and the filtrate was concentrated under reduced pressure. The residue was recrystallized from methanol to give the title compound (97.4 g, brown crystals). yield 86percent. melting point 88.1°C. 1H-NMR (300 MHz, CDCl3, TMS) δ: 1.94-2.02 (m, 4H), 3.19-3.26 (m, 4H), 6.39(d, J = 8 Hz, 2H), 7.25(d, J = 8 Hz, 2H). 13C-NMR (75 MHz, CDCl3, CDCl3) δ: 25.95, 48.14, 113.66, 132.15. mass spectrometry (EI-MS) Found; 225 [M]+, 224 [M-H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | Stage #1: With n-butyllithium In tetrahydrofuran at -70℃; for 0.333333 h; Inert atmosphere Stage #2: at -70℃; for 2 h; |
Reaction flask was added 0.1mol compound 1-a (reactants), 120ml of tetrahydrofuran (solvent), the sealing installation stirring, nitrogen replacement air, cooled to -70 deg.] C, at a concentration of 0.1mol dropwise 2.5M butyllithium ( reactant) added after 20 minutes, dry carbon dioxide gas is passed through (reactant) to saturation, the reaction at this temperature for 2 hours, the reaction solution was poured into 20ml of concentrated hydrochloric acid has (PH value adjustment) and water 100ml beaker hydrolysis, separated, and extracted with 50ml of ethyl acetate (solvent) aqueous phase was extracted once, and the combined organic phase was washed with brine until neutral, dried over anhydrous sodium sulfate (desiccant) sulfate, and the solvent was concentrated divisible, to give a pale yellow solid of toluene and twice with ethyl acetate twice (solvent) and recrystallized again to give white crystals 3-b, 90percent yield, HPLC purity was 98.0percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxaneReflux; Inert atmosphere | An argon-purged 1,4-dioxane (30 mL) wasadded to a flask containing bromophenylpyrrolidine 5b (722mg, 3.19mmol), (BPin)2 (= bis(pinacolato)diboron (1.21 g,4.78mmol), AcOK (939 mg, 9.56mmol), and PdCl2(dppf )(dppf = 1,1-bis(diphenylphosphino)ferrocene, 79 mg, 0.097mmol) and the mixture was refluxed under argon for 14 h.The reaction mixture was extracted with hexane, which wasdried over Na2SO4 and evaporated. The obtained residuewas chromatographed (SiO2, hexane/AcOEt = 17:3) to affordblack-red needles (575 mg, 2.10mmol, 66percent). TLC (SiO2,CHCl3): Rf = 0.60. 1H NMR (CDCl3): δ (ppm) = 1.32 (12H,s), 1.92.1(4H, m), 3.23.4(4H, m), 6.53 (2H, dd, J = 6.5,1.8 Hz), 7.67 (2H, dd, J = 6.5, 1.8 Hz). APCI-MS (CHCl3):m/z calcd for C16H25BNO2 ([MH]+), 274.1973; found,274.2256 |
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