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CAS No. : | 4487-57-4 | MDL No. : | MFCD09832226 |
Formula : | C5H2Br2N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | RZZGFCFQBVRQSX-UHFFFAOYSA-N |
M.W : | 281.89 | Pubchem ID : | 16099850 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 48.46 |
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) : | -6.32 cm/s |
Log Po/w (iLOGP) : | 1.44 |
Log Po/w (XLOGP3) : | 2.4 |
Log Po/w (WLOGP) : | 2.51 |
Log Po/w (MLOGP) : | 1.63 |
Log Po/w (SILICOS-IT) : | 0.66 |
Consensus Log Po/w : | 1.73 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.44 |
Solubility : | 0.103 mg/ml ; 0.000365 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.27 |
Solubility : | 0.15 mg/ml ; 0.000531 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.11 |
Solubility : | 0.221 mg/ml ; 0.000783 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 3.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.3 |
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 |
---|---|---|
75% | With phosphorus(V) oxybromide In acetonitrile at 20℃; for 3 h; Heating / reflux | Step 2.2, 4-Dibromo-5-nitropyridine Phosphorous oxybromide (5.73 g, 20 mmol) was added to a suspension of the product from Step 1 (1.70 g, 10 mmol) in acetonitrile (20 mL) at rt then heated to reflux for 3 h. The reaction mixture was cooled and carefully poured onto ice and sat. aq. K2C03 then extracted with EtOAc. The organic extracts were combined, washd with water and brine, dried (MgS04), filtered and concentrated to dive the title compound (2.1 g, 75 percent) as a dark solid. |
75% | With phosphorus(V) oxybromide In acetonitrile at 20℃; for 3 h; Heating / reflux | Step 2.2, 4-Dibromo-5-nitropyridine Phosphorous oxybromide (5.73 g, 20 mmol) was added to a suspension of the product from Step 1 (1.70 g, 10 mmol) in acetonitrile (20 mL) at rt then heated to reflux for 3 h. The reaction mixture was cooled and carefully poured onto ice and sat. aq. K2C03 then extracted with EtOAc. The organic extracts were combined, washd with water and brine, dried (MgS04), filtered and concentrated to dive the title compound (2.1 g, 75 percent) as a dark solid. |
66% | With phosphorus(V) oxybromide In acetonitrile at 90℃; for 4 h; | To a solution of 2-hydroxy-4-methoxy-5-nitropyridine (10 g, 59 mmole) in acetonitrile (60 mL) was added POBr3 (33.7 g, 117.6 mmole). The reaction mixture was heated to 9O0C for 4 h. The mixture was allowed to cool to RT and then poured onto saturated K2CO3ZiCe water. The product was extracted with EtOAc (2 x 250 mL), washed with brine and dried over Na2SO4. Concentration of the EtOAc solution under vacuum provided a light brown solid (10.9 g, 66percent) which was used without further purification: LC/MS: m/z 283 [M+H]+, single component. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41.1% | With phosphorus(V) oxybromide In acetonitrile at 80℃; for 2 h; Inert atmosphere | Into a 250 mL 3 -necked round-bottom flask purged and maintained with nitrogen was added a solution of 4-chloro-5-nitropyridin-2-ol (1 1.5 g, 65.9 mmol) in CH3CN (1 10 mL), followed by addition of POBr3 (23.1 g). The resulting solution was stirred at 80 °C for 2 hours. The solids were filtered out and the filtrate was concentrated under vacuum. The residue was suspended in 500 mL of ice water. The resulting solids were collected by filtration and dried under vacuum to afford 2,4- dibromo-5-nitropyridine (7.66 g, 41.1percent) as a light yellow solid, which was carried forward without purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With ammonia; triethylamine In tetrahydrofuran; methanol at 20℃; for 50 h; | Step 1. 2-bromo-5-nitro-4-pyridinamine Under nitrogen, to a solution of 2, 4-dibromo-5-nitropyridine in THF (150 mL), was added ammonia (2. OM in MeOH), followed with triethylamine (5mL). This mixture was then stirred at rt for 50 h. The reaction mixture was concentrated, taken up in EtOAC, filtered through a silica gel pad, and then concentrated in vacuo to afford the title compound (3.67 g, 95percent). |
95% | With ammonia; triethylamine In tetrahydrofuran; methanol at 20℃; for 50 h; | Step 1. 2-bromo-5-nitro-4-pyridinamine Under nitrogen, to a solution of 2, 4-dibromo-5-nitropyridine in THF (150 mL), was added ammonia (2. OM in MeOH), followed with triethylamine (5mL). This mixture was then stirred at rt for 50 h. The reaction mixture was concentrated, taken up in EtOAC, filtered through a silica gel pad, and then concentrated in vacuo to afford the title compound (3.67 g, 95percent). |
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