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CAS No. : | 80866-82-6 | MDL No. : | MFCD00004630 |
Formula : | C8H9BrO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HAOOGRLZVQWDBY-UHFFFAOYSA-N |
M.W : | 217.06 | Pubchem ID : | 612298 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.25 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 46.76 |
TPSA : | 29.46 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) : | -6.56 cm/s |
Log Po/w (iLOGP) : | 2.27 |
Log Po/w (XLOGP3) : | 1.5 |
Log Po/w (WLOGP) : | 1.8 |
Log Po/w (MLOGP) : | 1.95 |
Log Po/w (SILICOS-IT) : | 2.34 |
Consensus Log Po/w : | 1.97 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.4 |
Solubility : | 0.859 mg/ml ; 0.00396 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.73 |
Solubility : | 4.08 mg/ml ; 0.0188 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -3.21 |
Solubility : | 0.133 mg/ml ; 0.000611 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.39 |
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 |
---|---|---|
98% | With lithium bromide monohydrate; [bis(acetoxy)iodo]benzene In 2,2,2-trifluoroethanol at 20℃; for 0.166667 h; | General procedure: To a solution of alkoxybenzylalcohol 1 (0.2 mmol) in CF3CH2OH (1 mL) were added LiBr·H2O (0.2 mmol) and PhI(OAc)2 (0.2 mmol) atroom temperature. After completion of the reaction as indicated by TLC monitoring, saturated aq. Na2SO3 wasadded and the mixture was extracted with CH2Cl2. The combined organic layers were washed with brine, driedover anhydrous Na2SO4 and then concentrated in vacuo. The residue was purified by silica gel columnchromatography to afford pure monobrominated compounds 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With phosphorus tribromide In dichloromethane at 0℃; for 0.25 h; | 4-Bromo-2-(bromomethyl)-1-methoxybenzene. To a solution of (5-bromo-2-methoxyphenyl)methanol (1.0 g, 4.6 mmol) in dichloromethane (10 mL) at 0° C. was added tribromophosphine (1 M in dichloromethane, 9.2 mL, 9.2 mmol). The ice bath was removed and the reaction stirred for 15 min. The reaction was concentrated, poured onto cold saturated sodium bicarbonate, extracted with pentane, dried over magnesium sulfate, and concentrated to give 1.15 g (89percent) as a white crystalline solid. 1H NMR (500 MHz, CDCl3) δ ppm 7.44 (d, J=2.5 Hz, 1H), 7.38 (dd, J=8.9, 6.1 Hz, 1H), 4.47 (s, 2H), 3.87 (s, 3H); 13C NMR (126 MHz, CDCl3) δ ppm 156.7, 133.6, 132.8, 128.4, 112.8, 112.7, 56.0, 27.5. |
63% | With Oxalyl bromide; Triphenylphosphine oxide In chloroform for 7 h; | To a solution of Ph3PO (48.1 mg, 0.173 mmol) in CHCl3 (1.50 mL) was added oxalyl bromide (16.2 mL, 0.173 mmol) and the solution was stirred for 5 min. To the stirring solution was added 17 (250 mg, 1.15 mmol) in CHCl3 (1.00 mL) and oxalyl bromide (83.8 mL, 0.978 mmol) in CHCl3 (1.00 mL) over 7 hours via syringe pump. The solution was concentrated under reduced pressure and purification by flash chromatography (petroleum ether/EtOAc, 10:1) gave 18 (201 mg, 63percent) as a colourless solid, mp 114-116 °C, Rf 0.89 (petroleum ether/EtOAc, 10:1). IR: νmax (CHCl3) 3011, 2966, 2942, 2841, 1677, 1596, 1490, 1463, 1442, 1300, 1277, 1257, 1182, 1030 cm-1. 1H MNR: (400 MHz, CDCl3) δ 7.46 (1H, d, J=8.8, ArHmeta), 7.39 (1H, dd, J=8.8, 2.4, ArHmeta), 6.77 (1H, J=8.8, ArHortho), 4.49 (2H, s, ArCH2Br), 3.89 (3H, s, ArOCH3). 13C NMR: (100 MHz, CDCl3) δ 156.5 (Cq), 133.4 (CH), 132.7 (CH), 128.2 (Cq), 112.6 (Cq), 112.5 (CH), 55.8 (CH3), 27.5 (CH2). HRMS: (EI) m/z calculated for C8H8OBr2 277.8936, m/z found 277.8930. |
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