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CAS No. : | 23003-35-2 | MDL No. : | MFCD06655956 |
Formula : | C6H6BrNO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | UHMANLXCLQNQJD-UHFFFAOYSA-N |
M.W : | 188.02 | Pubchem ID : | 11959101 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.17 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 38.93 |
TPSA : | 33.12 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) : | -6.08 cm/s |
Log Po/w (iLOGP) : | 1.78 |
Log Po/w (XLOGP3) : | 1.92 |
Log Po/w (WLOGP) : | 1.86 |
Log Po/w (MLOGP) : | 0.92 |
Log Po/w (SILICOS-IT) : | 2.02 |
Consensus Log Po/w : | 1.7 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.71 |
Solubility : | 0.368 mg/ml ; 0.00196 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.24 |
Solubility : | 1.08 mg/ml ; 0.00577 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.69 |
Solubility : | 0.383 mg/ml ; 0.00204 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.67 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
88.3% | With potassium carbonate In acetone | b. 2-Bromo-3-methoxy-6-methyl-pyridine. A stirred mixture of 2-bromo-3-hydroxy-6-methyl-pyridine (7.89 g, 42.0 mmol), potassium carbonate (11.60 g, 83.9 mmol) and iodomethane (8.93 g, 62.9 mmol, 3.92 mL) in acetone (100 mL) was heated under reflux overnight. The mixture was filtered, evaporated and purified on silica gel (hexane:ethyl acetate, 95:5 to 9:1) to give the desired product as a white solid (7.49 g, 88.3percent). 1H NMR (500 MHz, CDCl3): δ2.46 (s, 3 H), 3.87 (s, 3 H), 7.04 (s, 2 H). |
88.3% | With potassium carbonate In acetone | b. 2-Bromo-3-methoxy-6-methyl-pyridine A stirred mixture of 2-bromo-3-hydroxy-6-methyl-pyridine (7.89 g, 42.0 mmol), potassium carbonate (11.60 g, 83.9 mmol) and iodomethane (8.93 g, 62.9 mmol, 3.92 mL) in acetone (100 mL) was heated under reflux overnight. The mixture was filtered, evaporated and purified on silica gel (hexane:ethyl acetate, 95:5 to 9:1) to give the desired product as a white solid (7.49 g, 88.3percent). 1H NMR (500 MHz, CDCl3): δ2.46 (s, 3H), 3.87 (s, 3H), 7.04 (s, 2H). |
42% | With potassium carbonate In acetone for 2 h; Reflux | [0124] To 2-bromo-6-methylpyridin-3-ol (XXXXIV) were added 50 ml of acetone, potassium carbonate (K2CO3) (2.0 g, 14.66 mmol) and iodomethane (684 μl, 10.99 mmol), and the resulting mixture was stirred with reflux for 2 hrs. After TLC was conducted, the solvent was removed and the mixture was extracted with 60 ml of ethylacetate (EA) and 60 ml of water. The organic layer was treated with magnesium sulfate (MgSO4) and filtered, and the solution was concentrated and purified through silica gel chromatography (normal hexane : ethylacetate = 10 : 1, v/v) to give the title compound as pale yellow crystals (772 mg, 3.82 mmol, 42 percent). 1H NMR (400 MHz, CDCl3) δ 7.06 (s, 2H), 3.89 (s, 3H), 2.48 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53.1% | With bromine In pyridine; water | a. 2-Bromo-3-hydroxy-6-methyl-pyridine. To a solution of 5-hydroxy-2-methylpyridine (8.80 g, 80.6 mmol) in 125 mL of pyridine was added a solution of bromine (14.18 g, 88.7 mmol) in 50 mL pyridine dropwise. The temperature of the reaction mixture rose to 40° C. upon completion of addition. After 1 hour the pyridine was removed under vacuum and the resulting solid was suspended into water (200 mL) and stirred overnight. The solid was collected and dried to give the desire product as a brownish solid (8.05 g, 53.1percent yield). 1H NMR (500 MHz, CDCl3): δ2.21 (s, 3 H), 6.73 (d, J=8.1 Hz, 1 H), 6.94 (d, J=8.1 Hz, 1 H), 9.36 (brs, 1 H). |
53.1% | With bromine In pyridine; water | a. 2-Bromo-3-hydroxy-6-methyl-pyridine To a solution of 5-hydroxy-2-methylpyridine (8.80 g, 80.6 mmol) in 125 mL of pyridine was added a solution of bromine (14.18 g, 88.7 mmol) in 50 mL pyridine dropwise. The temperature of the reaction mixture rose to 40° C. upon completion of addition. After 1 hour the pyridine was removed under vacuum and the resulting solid was suspended into water (200 mL) and stirred overnight. The solid was collected and dried to give the desire product as a brownish solid (8.05 g, 53.1percent yield). 1H NMR (500 MHz, CDCl3): δ2.21 (s, 3H), 6.73 (d, J=8.1 Hz, 1H), 6.94 (d, J=8.1 Hz, 1H), 9.36 (brs, 1H). |
37% | at 20℃; cooling with ice | 2-methyl-5-hydroxypyridine (4.4 g, 40.3 mmol) was suspended in pyridine (85 mL) and cooled at ice-water. The bromine (7.1 g, 44.3 mmol) was slowly dropped into above cooled suspension. The ice-water bath was removed after finished bromine addition and the mixture was stirred overnight at room temperature. The pyridine was removed in vacuo. The residue was treated with water (100 mL) and stirred for 1 h. The solid product 48 (2.8 g, 37percent) was collected by filtration. |
31.3% | With bromine In pyridine; water | (1) Synthesis of 6-bromo-5-hydroxy-2-methylpyridine [R4=Br in Compound (XIV)] To a solution obtained by dissolving 5-hydroxypicoline (10 g, 0.0916 mol) in pyridine (30 ml) was added dropwise bromine (15.4 g, 0.0916*1.05 mol), followed by stirring at room temperature for 4 hours. Pyridine was then distilled off by an evaporator. To the residue was added water and the precipitate was filtered out, washed with water to obtain a white solid. Yield: 5.38 g, percent yield: 31.3percent, m.p.: 185-187° C. IR KBr cm-1: 2776, 1563, 1296, 1221, 1083, 831. 1H-NMR (60 MHz, d6-DMSO, δ): 2.26 (3H, s, CH3), 6.93 (1H, d, J=8 Hz, pyridine ring H), 7.1 (1H, d, J=8 Hz, pyridine ring H), 10.2 (1H, s OH). |
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