3-AMINO-6-BROMOPYRIDINE-2-CARBOXYLIC ACID METHYL ESTER CAS#: 866775-09-9; ChemWhat Code: 1256619
Identification
| Product Name | 3-AMINO-6-BROMOPYRIDINE-2-CARBOXYLIC ACID METHYL ESTER |
| IUPAC Name | methyl 3-amino-6-bromopyridine-2-carboxylate |
| Molecular Structure |  |
| CAS Registry Number | 866775-09-9 |
| EINECS Number | No data available |
| MDL Number | MFCD11656228 |
| Beilstein Registry Number | No data available |
| Synonyms | methyl 3-amino-6-bromopicolinatemethyl 3-amino-6-bromopyridine-2-carboxylate |
| Molecular Formula | C7H7BrN2O2 |
| Molecular Weight | 231.047 |
| InChI | InChI=1S/C7H7BrN2O2/c1-12-7(11)6-4(9)2-3-5(8)10-6/h2-3H,9H2,1H3 |
| InChI Key | FETASVOVQOWEBL-UHFFFAOYSA-N |
| Canonical SMILES | COC(=O)c1c(ccc(n1)Br)N |
| Patent Information | ||
| Patent ID | Title | Publication Date |
| US2013/210819 | QUINAZOLINE DERIVATIVES | 2013 |
| US2015/57260 | ALKYNYL ALCOHOLS AND METHODS OF USE | 2015 |
Physical Data
| Appearance | Yellow to peal yellow solid |
| Solubility | No data available |
| Flash Point | No data available |
| Refractive index | No data available |
| Sensitivity | No data available |
Spectra
| Description (NMR Spectroscopy) | Nucleus (NMR Spectroscopy) | Solvents (NMR Spectroscopy) | Frequency (NMR Spectroscopy), MHz | Original Text (NMR Spectroscopy) |
| Chemical shifts | 1H | chloroform-d1 | 400 | |
| Chemical shifts | 13C | chloroform-d1 | 100 | |
| Chemical shifts | 1H | chloroform-d1 | 400 | 1H NMR (400 MHz, CDCl3) δ=7.35 (d, J=8.4 Hz, 1H), 6.96 (d, J=8.4 Hz, 1H), 5.83 (br. s, 1H), 3.96 (s, 3H) |
| Chemical shifts | 1H | chloroform-d1 | 300 | 1H- NMR(300MHz,CDCl3)δ3.94(3H,s),5.81(2H,brs),6.93(1H,d,J=8.72Hz), 7.32(1H,d,J=8.71Hz) |
| Description (Mass Spectrometry) | Peak |
| electrospray ionisation (ESI), liquid chromatography mass spectrometry (LCMS), time-of-flight mass spectra (TOFMS), spectrum | |
| electrospray ionisation (ESI), spectrum | |
| liquid chromatography mass spectrometry (LCMS), electrospray ionisation (ESI), spectrum | 231 m/z, 233 m/z |
| liquid chromatography mass spectrometry (LCMS), electrospray ionisation (ESI), spectrum | |
| fast atom bombardment (FAB), spectrum | 232.9 m/z |
| 3-AMINO-6-BROMOPYRIDINE-2-CARBOXYLIC ACID METHYL ESTER CAS#: 866775-09-9 MASS |  |
Route of Synthesis (ROS)
| Conditions | Yield |
| With hydrogen In ethyl acetate at 20℃; under 7600.51 Torr; for 6h; Autoclave; | 99% |
| With 0.2C27H36N2*Pt; hydrogen In tetrahydrofuran at 60℃; under 3000.3 Torr; for 5h; chemoselective reaction; | 99% |
| With hydrogen In ethyl acetate under 760.051 Torr; for 2h; Heating; Flow reactor; Green chemistry; | 99% |
| With hydrogen; triethylamine In ethanol; water at 110℃; under 30003 Torr; for 24h; Autoclave; | 98% |
| With hydrogen In 2-methyltetrahydrofuran; water at 40℃; under 15001.5 Torr; for 24h; chemoselective reaction; | 98% |
| With sodium tetrahydroborate In water at 20℃; for 1.5h; chemoselective reaction; Experimental Procedure General procedure: In a typical experiment, 0.5mmol of nitroarene and 0.002g(2mol%) NiNPs/DNA were added to 2mL water and thenstirred for 2-3min for thoroughly mixing. Subsequently,1mmol of NaBH4was added to the reaction mixture undermagnetic stirring at room temperature. The extent of thereaction was monitored by thin layer chromatography.Reproducibility of the results was checked by repeating theruns at least three times and was found to be within acceptablelimits (± 3%). When the reaction was completed, thereaction mixture was diluted with ethyl acetate and the catalystwas recovered by centrifugation. The combined organicfractions were dried over Na2SO4and evaporated underreduced pressure. The crude product was purified by columnchromatography on silica gel with a mixture of ethyl acetateand n-hexane as the eluent, and the ratio of ethyl acetate andn-hexane was depended on the structure of the products.The structure of isolated products was verified by 1H NMR. | 97% |
Safety and Hazards
| GHS Hazard Statements | Not Classified |
Other Data
| Transportation | Under the room temperature and away from light |
| HS Code | No data available |
| Storage | Store at 2-8°C for long time. |
| Shelf Life | 1 year |
| Market Price | USD |
| Druglikeness | |
| Lipinski rules component | |
| Molecular Weight | 231.049 |
| logP | 1.294 |
| HBA | 4 |
| HBD | 1 |
| Matching Lipinski Rules | 4 |
| Veber rules component | |
| Polar Surface Area (PSA) | 65.21 |
| Rotatable Bond (RotB) | 2 |
| Matching Veber Rules | 2 |
| Use Pattern |
| 3-AMINO-6-BROMOPYRIDINE-2-CARBOXYLIC ACID METHYL ESTER CAS#: 866775-09-9 is used as the intermediate of API. |
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Approved Manufacturers | |
| Caming Pharmaceutical Ltd | http://www.caming.com/ |
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