Methyl 6-amino-3-bromopicolinate manufacturers
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| | Methyl 6-amino-3-bromopicolinate Basic information |
| Product Name: | Methyl 6-amino-3-bromopicolinate | | Synonyms: | Methyl 6-amino-3-bromopicolinate;Methyl 6-amino-3-bromopyridine-2-carboxylate;methyl 6-amino-3-bromo-2-pyridinecarboxylate;6-Amino-3-bromo-pyridine-2-carboxylic acid methyl ester;2-Pyridinecarboxylic acid, 6-amino-3-bromo-, methyl ester;Methyl 6-amino-3-bromopicolinate ISO 9001：2015 REACH;2-Pyridinecarboxylic acid, 6-amino-3-bromo-, methyl ester (9CI, ACI);6-amino-3-bromo-2-Pyridinecarboxylic acid methyl ester (9CI ACI) | | CAS: | 178876-83-0 | | MF: | C7H7BrN2O2 | | MW: | 231.05 | | EINECS: | | | Product Categories: | blocks;Bromides;Carboxes;Pyridines | | Mol File: | 178876-83-0.mol |  |
| | Methyl 6-amino-3-bromopicolinate Chemical Properties |
| Boiling point | 333.4±37.0 °C(Predicted) | | density | 1.662±0.06 g/cm3(Predicted) | | storage temp. | Keep in dark place,Inert atmosphere,Room temperature | | pka | 1.12±0.10(Predicted) | | form | solid | | color | Off white | | InChI | InChI=1S/C7H7BrN2O2/c1-12-7(11)6-4(8)2-3-5(9)10-6/h2-3H,1H3,(H2,9,10) | | InChIKey | YJUKTIBOUBUOJH-UHFFFAOYSA-N | | SMILES | C1(C(OC)=O)=NC(N)=CC=C1Br |
| Hazard Codes | Xi | | HS Code | 2933399990 |
| | Methyl 6-amino-3-bromopicolinate Usage And Synthesis |
| Synthesis | General procedure for the synthesis of methyl 6-amino-3-bromopyridine-2-carboxylate and methyl 5-bromo-6-aminopyridine-2-carboxylate from methyl 6-aminopyridine-2-carboxylate:
(d) Synthesis of methyl 6-amino-5-bromopyridine-2-carboxylate: to a solution of methyl 6-aminopyridine-2-carboxylate (10 g, 66.0 mmol) in chloroform (450 mL) was slowly added a solution of bromine (3.4 mL, 66.0 mmol) in chloroform (100 mL) at room temperature, and the reaction mixture was stirred for 40 hours. After completion of the reaction, the reaction mixture was diluted with chloroform and washed sequentially with saturated sodium thiosulfate solution and water. The organic phase was dried with anhydrous sodium sulfate and concentrated under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography using ethyl acetate/hexane as eluent to afford methyl 6-amino-3-bromopyridine-2-carboxylate as a yellow solid (3.3 g, 22% yield). Mass spectrum (ESI) m/e: 231.0 [M+H]+. 1H NMR (CDCl3, 400MHz): δ (ppm) = 7.76 (d, J = 7.88Hz, 1H), 7.34 (d, J = 7.92Hz, 1H), 5.23 (s, 2H), 3.94 (s, 3H).
d) Isolation of methyl 6-amino-3-bromopyridine-2-carboxylate: In step d) above, the isomer methyl 6-amino-3-bromopyridine-2-carboxylate (3.0 g, 19% yield) was also isolated as a by-product. Mass spectrum (ESI) m/e: 231.2 [M+H]+. 1H NMR (CDCl3, 400MHz): δ (ppm) = 7.60 (d, J = 8.72Hz, 1H), 6.47 (d, J = 7.88Hz, 1H), 4.71 (s, 2H), 3.94 (s, 3H). | | References | [1] Journal of Organic Chemistry, 1996, vol. 61, # 14, p. 4623 - 4633
[2] Organic Process Research and Development, 2010, vol. 14, # 1, p. 263 - 271
[3] Tetrahedron Letters, 2010, vol. 51, # 38, p. 5035 - 5037
[4] Patent: US2011/190269, 2011, A1. Location in patent: Page/Page column 61-62
[5] Patent: WO2011/92272, 2011, A1. Location in patent: Page/Page column 129; 130 |
| | Methyl 6-amino-3-bromopicolinate Preparation Products And Raw materials |
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