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CAS No. : | 29558-77-8 | MDL No. : | MFCD00059076 |
Formula : | C12H9BrO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ARUBXNBYMCVENE-UHFFFAOYSA-N |
M.W : | 249.10 | Pubchem ID : | 95093 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 61.6 |
TPSA : | 20.23 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -4.5 cm/s |
Log Po/w (iLOGP) : | 2.28 |
Log Po/w (XLOGP3) : | 4.67 |
Log Po/w (WLOGP) : | 3.82 |
Log Po/w (MLOGP) : | 3.75 |
Log Po/w (SILICOS-IT) : | 3.72 |
Consensus Log Po/w : | 3.65 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.89 |
Solubility : | 0.00317 mg/ml ; 0.0000127 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -4.82 |
Solubility : | 0.00375 mg/ml ; 0.0000151 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -5.2 |
Solubility : | 0.00158 mg/ml ; 0.00000635 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 1.38 |
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: |
* 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 |
---|---|---|
95.9% | With potassium carbonate In butanone for 8 h; Reflux | General procedure: A suspension of 4-bromo-4'-hydroxybiphenyl (13) (3.5 g, 14.11 mmol), 1-bromoheptane (3.75 g, 21.05 mmol) and K2CO3 (4.9 g, 35.28 mmol) in 2-butanone (25 mL) was refluxed for 8 h. After cooling, the reaction mixture was diluted by CH2Cl2 (50 mL). After filtration, the organic layer was washed by H2O (50 mL) and saturated brine (50 mL), dried over anhydrous Na2SO4, and filtrated. The solvent was condensed to 15 mL under reduced pressure, and the residue was collected and washed by cool hexane (0 °C) to afford 14c (4.6 g, yield 94.3percent) as white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With sodium hydroxide; tetrabutylammomium bromide In water | Alternative Preparation of 4-bromo-4'-pentyloxybiphenyl 1(a): 4-Bromo-4'-hydroxybiphenyl (12.5 g, 50.2 mmol) was added to a solution of NaOH (2.28 g, 97percent pure, 55.2 mmol) in deionized H2O (150 ml), followed by the addition of 1-iodopentane (11.9 g, 60.2 mmol) and tetrabutylammonium bromide (0.82 g, 2.5 mmol). The mixture was stirred at 90° C. for 3.75 h until the solids went into solution. Then, as the reaction proceeded, the desired product began to precipitate. The mixture was slowly cooled and then filtered to provide a solid which was washed with deionized water until the pH of the filtrate was neutral and then dried for 16 h in a vacuum oven at 30° C. Yield: 15.41 g (96percent) of 5a. Rf 0.5 (97:3 hexanes/EtOAc). 1H NMR: δ 0.93 (t, 3H, J=6.9 Hz); 1.41 (m, 4H); 1.79 (m, 2H); 3.97 (t, 2H, J=6.6 Hz); 6.98 (m, 2H); 7.23 (m,6H). 13C NMR: δ 14.03; 22.43; 28.22; 28.98; 68.12; 114.91; 120.71; 127.93; 128.27; 131.77; 132.24; 139.82; 159.03. MS(FAB+): m/z 320. IR(CHCl3): 2960, 2936, 2874, 1608, 1518, 1485, 1475 cm-1 Analysis for C17H19BrO: Calcd: C, 63.96; H. 6.00; Br, 25.0; Found: C, 64.10; H. 5.97; Br, 25.28. |
96% | With sodium hydroxide; tetrabutylammomium bromide In water | Alternative Preparation of 4-bromo-4'-pentyloxybiphenyl 1(a): 4-Bromo-4'-hydroxybiphenyl (12.5 g, 50.2 mmol) was added to a solution of NaOH (2.28 g, 97percent pure, 55.2 mmol) in deionized H2O (150 ml), followed by the addition of 1-iodopentane (11.9 g, 60.2 mmol) and tetrabutylammonium bromide (0.82 g, 2.51 mmol). The mixture was stirred at 90° C. for 3.75 h until the solids went into solution. Then, as the reaction proceeded, the desired product began to precipitate. The mixture was slowly cooled and then filtered to provide a solid which was washed with deionized water until the pH of the filtrate was neutral and then dried for 16 h in a vacuum oven at 30° C. Yield: 15.41 g (96percent) of 5a. Rf 0.5 (97:3 hexanes/EtOAc). 1H NMR: δ0.93 (t, 3H, J=6.9 Hz); 1.41 (m, 4H); 1.79 (m, 2H); 3.97 (t, 2H, J=6.6 Hz); 6.98 (m, 2H); 7.23 (m, 6H). 13C NMR: δ14.03; 22.43; 28.22; 28.98; 68.12; 114.91; 120.71; 127.93; 128.27; 131.77; 132.24; 139.82; 159.03. MS(FAB+): m/z 320. IR(CHC13): 2960, 2936, 2874, 1608, 1518, 1485, 1475 cm-1. Analysis for C17H19BrO: Calcd: C, 63.96; H. 6.00; Br, 25.0; Found: C, 64.10; H. 5.97; Br, 25.28. |