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CAS No. : | 30951-66-7 | MDL No. : | MFCD11870097 |
Formula : | C9H11BrO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ZRFMJMFYMQAUDO-UHFFFAOYSA-N |
M.W : | 215.09 | Pubchem ID : | 15072383 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.33 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 49.77 |
TPSA : | 20.23 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) : | -5.66 cm/s |
Log Po/w (iLOGP) : | 2.44 |
Log Po/w (XLOGP3) : | 2.75 |
Log Po/w (WLOGP) : | 2.57 |
Log Po/w (MLOGP) : | 2.91 |
Log Po/w (SILICOS-IT) : | 2.69 |
Consensus Log Po/w : | 2.67 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.24 |
Solubility : | 0.123 mg/ml ; 0.000571 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.83 |
Solubility : | 0.318 mg/ml ; 0.00148 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.5 |
Solubility : | 0.0674 mg/ml ; 0.000313 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.34 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
93% | Stage #1: at 6 - 20℃; for 3.66667 h; Stage #2: With hydrogenchloride In tetrahydrofuran; diethyl ether; water at 0℃; |
EXAMPLE 76; Preparation of N- [ (lS, 2R)-3- { [l- (3-bromophenyl)-l- methylethyl] amino}-1- (3, 5-difluorobenzyl)-2-hydroxypropyl] acetamide; 32 Scheme 8 O Br MeMgBr g NaN3 Br '°H Bu OMe OH Nh THF TFA THF 4 | kOH SOH 4 reflux H 19 H HOH H N, 1) TFA-0 zon F F 0 HCI 2) Ac-Im F 31 3) HCI 30 30 F 31 F NaOH HOH H Bu F 32 Step 1; Preparation of 2- (3-bromophenyl)-2-propanol 27; To 75 mmol of methylmagnesium bromide in 25 mL of ether stirring at 6 °C is added, dropwise over 10 min, a solution of methyl-3-bromobenzoate (4.3 g, 20 mmol) in 25 mL of dry THF. The mixture is then allowed to warm to ambient temperature and stirred for 3.5 h, then cooled to 0°C and quenched by dropwise addition of aqueous 10percent HC1. The acidified mixture is extracted twice with ethyl acetate, and the combined organic phases are washed with 1 N NaHC03 and with brine. The solution is dried over Na2SO4, concentrated, and chromatographed over silica gel, eluting with 15percent ethyl acetate in heptane, to afford 4.00 g (18.6 mmol, 93percent) of 2- (3-bromophenyl)-2- propanol 27 as a pale yellow oil |
14.9 g | at -78 - 20℃; for 2 h; | To a solution of methyl 3-bromobenzoate (15.0 g, 69.8 mmol) in THF (140 mL) at -78 °C was added dropwise a solution of MeMgBr/diethyl ether [3.0M] (58 mL). The reaction mixture was warmed up to room temperature and stirred for 2 h. The solution was poured to an aqueous saturated solution of ammonium chloride and the organic material was extracted with EtOAc. The organic layer was dried over Na2S04, filtered and concentrated to afford the corresponding alcohol (14.9 g) which was used without further purification. |
14.9 g | at -78 - 20℃; for 2 h; | To a solution of methyl 3-bromobenzoate (15.0 g, 69.8 mmol) in THF (140 mL) at −78° C. was added dropwise a solution of MeMgBr/diethyl ether [3.0M] (58 mL). The reaction mixture was warmed up to room temperature and stirred for 2 h. The solution was poured to an aqueous saturated solution of ammonium chloride and the organic material was extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and concentrated to afford the corresponding alcohol (14.9 g) which was used without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | at 0 - 20℃; for 4 h; | A solution of 3N METHYLMAGNESIUM bromide (6.53 mL, 19.59 mmol, 3 eq) in diethyl ether was cooled to 0 °C and treated with 3-bromoacetophenone (1.3 g, 6.53 MMOL). The reaction was stirred at room temperature for 4 h. The reaction was diluted with ethyl acetate and water. The layers were separated and the organic was washed with saturated sodium bicarbonate, 2N HCI, brine and dried over magnesium sulfate. The solvent was removed at reduced pressure and purified on the MPLC (Biotage) eluted with 5-10percent ethyl acetate-hexane to afford 1.2 g (90 percent) of the product. Rf = 0.22 (silica, ethyl acetate: hexanes, 1: 9) ; H-NMR (DMSO-D6) 8 7.63 (t, J = 1.8 Hz, 1H), 7.45 to 7.35 (m, 2H), 7.25 (t, J = 7.7, 1H), 5.15 (s, 1H), 1.39 (s, 6H). |
90% | Stage #1: at 0 - 20℃; for 4 h; Stage #2: With water In diethyl ether; ethyl acetate |
Example 22; Method H-15; Preparation of 2-(3-Bromo-phenyl)-propan-2-ol; A solution of 3N methylmagnesium bromide (6.53 mL, 19.59 mmol, 3 eq) in diethyl ether was cooled to 0 °C and treated with3-bromoacetophenone (1.3 g, 6.53 mmol). The reaction was stirred at room temperature for 4 h. The reaction was diluted with ethyl acetate and water. The layers were separated and the organic was washed with saturated sodium bicarbonate, 2N HCI, brine and dried over magnesium sulfate. The solvent was removed at reduced pressure and purified on the MPLC (Biotage) eluted with 5-10percent ethyl acetate-hexane to afford 1.2 g (90 percent) of the product. Rf = 0.22 (silica, ethyl acetate: hexanes, 1: 9) ; 1H-NMR (DMSO-d6) 6 7.63 (t, J = 1.8 Hz, 1H), 7.45 to 7.35 (m, 2H), 7.25 (t, J = 7. 7, 1H), 5.15 (s, 1H), 1.39 (s, 6H). |
90% | Stage #1: at 0℃; for 4 h; Stage #2: With water In diethyl ether; ethyl acetate |
Preparation of 2-(3-Bromo-phenvl)-propan-2-ol. A solution of 3N methylmagnesium bromide (6.53 mL, 19.59 mmol, 3 eq) in diethyl ether was cooled to 0 0C and treated with3-bromoacetophenone (1.3 g, 6.53 mmol). The reaction was stirred at room temperature for 4 h. The reaction was diluted with ethyl acetate and water. The layers were separated and the organic was washed with saturated sodium bicarbonate, 2N HCl, brine and dried over magnesium sulfate. The solvent was removed at reduced pressure and purified on theMPLC (Biotage) eluted with 5-10percent ethyl acetate - hexane to afford 1.2 g (90 percent) of the product. Rf = 0.22 (silica, ethyl acetate:hexanes, 1:9); 1H-NMR (DMSO-d6) 7.63 (t, J = 1.8 Hz, IH), 7.45 to 7.35 (m, 2H), 7.25 (t, J = 7.7, IH), 5.15 (s, IH), 1.39 (s, 6H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
4.98 g | Stage #1: With magnesium In diethyl etherReflux Stage #2: for 3 h; Reflux |
A solution of methylmagnesium iodide is prepared from 5.79 ml of methyl iodide and 2.2 g of magnesium turnings in refluxing ether. A solution of 5 g of methyl 3- bromobenzoate in 110 ml of ether is then added dropwise and the mixture is refluxed for 3 hours. The reaction mixture is poured onto ice/saturated NH4C1, the phases are separated by settling, the organic phase is washed with 10percent aHC03 solution and with saturated NaCl solution, and dried over MgS04, and the solvent is evaporated off under vacuum. 4.98 g of the expected compound are obtained. |
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