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CAS No. : | 30683-23-9 | MDL No. : | MFCD01320380 |
Formula : | C6H4BrNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KBDIRPOTVAODSA-UHFFFAOYSA-N |
M.W : | 202.01 | Pubchem ID : | 2050129 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 38.9 |
TPSA : | 50.19 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) : | -6.54 cm/s |
Log Po/w (iLOGP) : | 1.13 |
Log Po/w (XLOGP3) : | 1.4 |
Log Po/w (WLOGP) : | 1.54 |
Log Po/w (MLOGP) : | -0.34 |
Log Po/w (SILICOS-IT) : | 1.43 |
Consensus Log Po/w : | 1.03 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -2.35 |
Solubility : | 0.897 mg/ml ; 0.00444 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.06 |
Solubility : | 1.77 mg/ml ; 0.00875 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.26 |
Solubility : | 1.12 mg/ml ; 0.00555 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.37 |
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 |
---|---|---|
82% | With sulfuric acid In methanol at 20℃; for 12 h; | a) To the methanol solution of compound 16a (1 g, 4.9 mmol, Matrix) at room temperature was added a few drops of concentrated sulfuric acid. The mixture was stirred for 12 hours. After removal of MeOH, the crude residue was purified on silica gel column on CombiFlash.(R). with 20-50percent EtOAc in hexane to provide compound 16b (450 mg, 41percent). Compound 17 (yield 82percent) was synthesized following the procedure described in Example 1 for preparing compound 4 starting from compound 16b. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | Stage #1: With sodium hydride In DMF (N,N-dimethyl-formamide) at 0℃; for 0.833333 h; Stage #2: at 0 - 20℃; for 48 h; |
Sodium hydride (0.238 g of a 60percent dispersion in mineral oil, 5.95 mmol) was added to a stirred solution of 3-bromopyridine-2-carboxylic acid (1.00 g, 4.95 mmol) in DMF (18mL) at 0° C. under nitrogen. The mixture was stirred for 50 min and methyl iodide (0.31 mL, 4.98 mmol) was then added dropwise. The mixture was allowed to warm up gradually to room temperature and was stirred for 2 days. Water was added and the mixture evaporated in vacuo. The residue was partitioned between dichloromethane and water and the aqueous layer separated and re-extracted with dichloromethane (.x.2). The combined organic layers were dried (MgSO4) and evaporated in vacuo and the residue purified by flash chromatography on silica gel, eluting with 80percent ethyl acetate in hexane, to give the title-ester (0.77 g, 72percent), 1H NMR (400 MHz, CDCl3) δ8.62 (1H, dd, J=4.6 and 1.4 Hz), 8.01 (1H, dd, J=8.2 and 1.4 Hz), 7.31 (1H, dd, J=8.2 and 4.6 Hz), 4.02 (3H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | Heating / reflux | A mixture of 5.45 g of 3-bromo-2-pyridine carboxylic acid (27.0 mmol, 1 eq.), obtained in example 3b), in 100 ml of methanol is reflux heated in the presence of 8 ml of sulfuric acid. The reaction mixture is allowed to return to ambient temperature and poured into water. It is extracted 3 times with ethyl acetate, the organic phase is dried on Na2SO4 and vacuum evaporated. 2.48 g (42percent) of esterified product is obtained. NMR (1H, CDCl3): 4.02 (s; 3H), 7.34 (dd, J=8.2, 2.8 Hz; 1H), 8.04 (d, J=8.2 Hz; 1H), 8.64 (d, J=2.8 Hz; 1H). |
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