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CAS No. : | 186593-42-0 | MDL No. : | MFCD08688606 |
Formula : | C6H5BrN2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | QWAOQTGMEGSRLN-UHFFFAOYSA-N |
M.W : | 217.02 | Pubchem ID : | 18458822 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.17 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 45.73 |
TPSA : | 58.71 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) : | -6.37 cm/s |
Log Po/w (iLOGP) : | 1.51 |
Log Po/w (XLOGP3) : | 1.77 |
Log Po/w (WLOGP) : | 2.06 |
Log Po/w (MLOGP) : | 1.2 |
Log Po/w (SILICOS-IT) : | 0.34 |
Consensus Log Po/w : | 1.38 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.64 |
Solubility : | 0.499 mg/ml ; 0.0023 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.62 |
Solubility : | 0.52 mg/ml ; 0.00239 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.65 |
Solubility : | 0.484 mg/ml ; 0.00223 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.01 |
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 |
---|---|---|
81% | Stage #1: With sodium hydride In diethyl ether at 15℃; for 0.0833333 h; Stage #2: at 26 - 114℃; for 1.5 h; Stage #3: With sulfuric acid In water for 8 h; Heating / reflux |
Step 3: To a cooled (15° C.) solution of diethyl malonate (8.8 mL; 58 mmol) in diethyl ether (110 mL) was added NaH (as a 60percent dispersion in oil; 2.32 g; 58 mmol) over 5 min and 3-bromo-2-chloro-5-nitropyridine (12.5 g; 52.6 mmol) in four portions over 15 min (an exotherm to 26° C. was observed), followed by removal of diethyl ether in vacuo to give a red oil. After stirring the resulting red oil at 114° C. for 1 h 15 min, H2SO4 (6M, 67 mL) was added. The resulting mixture was heated at reflux for 8 h then cooled to 0° C. and the pH value was adjusted to 7 with 25percent KOH aqueous solution (135 mL). The resulting mixture was stirred in an ice bath for 25 min and the crude product was collected and washed with water (50 mL) by filtration. The crude product was stirred in CH2Cl2 (350 mL) for 30 min and the impurity was removed by filtration. The organic layer was dried over Na2SO4, filtered and concentrated to give 11.1 g of the impure product as red oil. The red oil was dissolved in CH2Cl2 (100 mL) and hexanes (200 mL). The resulting mixture was filtered and the organic portion was concentrated to give 9.3 g of 3-bromo-2-methyl-5-nitropyridine as an orange crystalline solid (81percent yield). 1H NMR (CDCl3) δ 9.25 (d, J=2.3 Hz, 1H), 8.61 (d, J=2.3 Hz, 1H), 2.80 (s, 3H). |
81% | Stage #1: With sodium hydride In diethyl ether at 15℃; for 0.0833333 h; Stage #2: at 26 - 114℃; for 1.5 h; Stage #3: With sulfuric acid In diethyl ether; water for 8 h; Heating / reflux |
To a cooled (15° C.) solution of diethyl malonate (8.8 mL, 58.0 mmol) in diethyl ether (110 mL) was added NaH (60percent dispersion in oil, 2.32 g, 58.0 mmol) over 5 min and 3-bromo-2-chloro-5-nitropyridine (12.5 g, 52.6 mmol) in four portions over 15 min (an exotherm to 26° C. was observed), followed by removal of diethyl ether in vacuo to give a red oil. After stirring the resulting red oil at 114° C. for 1 h 15 min, H2SO4 (6M, 67.0 mL) was added. The resulting mixture was heated at reflux for 8 h then cooled to 0° C. and the pH value was adjusted to 7 with 25percent KOH aqueous solution (135 mL). The resulting mixture was stirred in an ice bath for 25 min and the crude product was collected and washed with water (50 mL) by filtration. The crude product was stirred in CH2Cl2 (350 mL) for 30 min and the impurity was removed by filtration. The organic layer was dried over Na2SO4, filtered and concentrated to give the impure product as red oil (11.1 g). The red oil was dissolved in CH2Cl2 (100 mL) and hexanes (200 mL). The resulting mixture was filtered and the organic portion was concentrated in vacuo to give 3-bromo-2-methyl-5-nitropyridine as an orange crystalline solid (9.30 g, 81percent yield). 1H NMR (CDCl3) δ 9.25 (d, J=2.3 Hz, 1H), 8.61 (d, J=2.3 Hz, 1H), 2.80 (s, 3H). |
81% | Stage #1: With sodium hydride In diethyl ether at 15℃; for 0.0833333 h; Stage #2: at 26 - 114℃; for 1.5 h; Stage #3: With sulfuric acid In water for 8 h; Heating / reflux |
Step 3: To a cooled (15° C.) solution of diethyl malonate (8.8 mL, 58 mmol) in diethyl ether (110 mL) was added NaH (as a 60percent dispersion in oil, 2.32 g, 58 mmol) over 5 min and 3-bromo-2-chloro-5-nitropyridine (12.5 g, 52.6 mmol) was added in four portions over ~15 min (an exotherm to 26° C. was observed), followed by removal of diethyl ether in vacuo to give a red oil. After stirring the resulting red oil at 114° C. for 1 h 15 min, H2SO4 (6M, 67 mL) was added. The resulting mixture was heated at reflux for 8 h then cooled to 0° C. and the pH value was adjusted to 7 with 25percent KOH aqueous solution (135 mL). The resulting mixture was stirred in an ice bath for 25 min and the crude product was collected and washed with water (50 mL) by filtration. The crude product was stirred in CH2Cl2 (350 mL) for 30 min and the impurity was removed by filtration. The organic layer was dried over Na2SO4, filtered and concentrated to give 11.1 g of the impure product as red oil. The red oil was dissolved in CH2Cl2 (100 mL) and hexanes (200 mL). The resulting mixture was filtered and the organic portion was concentrated to give 9.3 g of 3-bromo-2-methyl-5-nitropyridine as an orange crystalline solid (81percent yield). 1H NMR (CDCl3) δ 9.25 (d, J=2.3 Hz, 1H), 8.61 (d, J=2.3 Hz, 1H), 2.80 (s, 3H). |
81% | Stage #1: With sodium hydride In diethyl ether at 15 - 114℃; for 1.58333 h; Stage #2: With sulfuric acid In water |
To a cooled (15° C.) solution of diethyl malonate (8.8 mL; 58.0 mmol) in diethyl ether (110 mL) was added NaH (as a 60percent dispersion in oil; 2.32 g; 58.0 mmol) over 5 min and 3-bromo-2-chloro-5-nitropyridine (12.5 g; 52.6 mmol) in four portions over 15 min (an exotherm to 26° C. was observed), followed by removal of diethyl ether in vacuo to give a red oil. After stirring the resulting red oil at 114° C. for 1 h 15 min, H2SO4 (6M, 67.0 mL) was added. The resulting mixture was heated at reflux for 8 h then cooled to 0° C. and the pH value was adjusted to 7 with 25percent KOH aqueous solution (135 mL). The resulting mixture was stirred in an ice bath for 25 min and the crude product was collected and washed with water (50 mL) by filtration. The crude product was stirred in CH2Cl2 (350 mL) for 30 min and the impurity was removed by filtration. The organic layer was dried over Na2SO4, filtered and concentrated to give 11.1 g of the impure product as red oil. The red oil was dissolved in CH2Cl2 (100 mL) and hexanes (200 mL). The resulting mixture was filtered and the organic portion was concentrated to give 9.30 g of 3-bromo-2-methyl-5-nitropyridine as an orange crystalline solid (81percent). 1H NMR (CDCl3) δ 9.25 (d, J=2.3Hz, 1H), 8.61 (d, J=2.3Hz, 1H), 2.80 (s, 3H). |
0.65 mg | Stage #1: With sodium hydroxide In diethyl ether for 0.0833333 h; Stage #2: With sulfuric acid In diethyl ether for 8 h; Reflux |
intothe mixture of Diethyl ether (30 ml) solution having diethyl Malonate (5 mmol)was added into the Sodium hydroxide (5 mmol)and stirred for 5mins. Again slowlyadded 3-bromo-2-cholro - 5- Nitropyridine (4.2mmol)and after stirring for 5 min the solvent was removed to give ared oily compound. At 114 ° C the oily mixture was stirred for 1.5 hours, 6Msulfuric acid (5.8 ml) and at reflux stirred for 8 hours. After cooling to 0 °C, with 25percent aqueous potassium hydroxide solution adjusted pH to 7 .theresulting precipitate was collected by filtration then it was washed with water and dried to give 0.65 g ofthe title compound |
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