5-Bromo-2-hydroxynicotinic acid CAS 104612-36-4
5-Bromo-2-hydroxynicotinic acid Basic information
| Product Name: | 5-Bromo-2-hydroxynicotinic acid |
| Synonyms: | 2-Hydroxy-5-bromonicotinic acid;5-BROMO-2-HYDROXYNICOTINIC ACID HPLC 99%;3-Pyridinecarboxylic acid, 5-bromo-2-hydroxy-;5-Bromo-2-hydroxynicotinic acid ,98%;5-Bromo-2-hydroxynic;5-BroMo-2-hydroxynicotini...;5-Bromo-2-hydroxypyridine-3-carboxylic acid, 5-Bromo-3-carboxy-2-hydroxypyridine;5-broMo-2-hydroxypyridin-3-carboxylic acid |
| CAS: | 104612-36-4 |
| MF: | C6H4BrNO3 |
| MW: | 218 |
| EINECS: | 692-269-1 |
| Product Categories: | pharmacetical;Carboxylic Acids;Pyridine;blocks;Bromides;Carboxes;Pyridines;Carboxylic Acids |
| Mol File: | 104612-36-4.mol |
5-Bromo-2-hydroxynicotinic acid Chemical Properties
| Melting point | 287°C |
| Boiling point | 354.7±42.0 °C(Predicted) |
| density | 2.015±0.06 g/cm3(Predicted) |
| Fp | 287°C |
| storage temp. | Inert atmosphere,Room Temperature |
| pka | 2.09±0.20(Predicted) |
| form | powder to crystal |
| color | Light orange to Yellow to Green |
| Decomposition | 287 ºC |
| InChI | InChI=1S/C6H4BrNO3/c7-3-1-4(6(10)11)5(9)8-2-3/h1-2H,(H,8,9)(H,10,11) |
| InChIKey | GYXOTADLHQJPIP-UHFFFAOYSA-N |
| SMILES | C1(=O)NC=C(Br)C=C1C(O)=O |
| CAS DataBase Reference | 104612-36-4(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xi |
| Hazard Note | Irritant/Keep Cold |
| HazardClass | IRRITANT |
| HS Code | 29333990 |
| Chemical Properties | white to light yellow crystal |
| Synthesis Reference(s) | Synthetic Communications, 19, p. 553, 1989 DOI: 10.1080/00397918908050699 Synthesis, p. 528, 2002 DOI: 10.1055/s-2002-20959 |
| Synthesis | 609-71-2 104612-36-4 General procedure for the synthesis of 5-bromopyridine-3-carboxylic acid-2-one from 2-hydroxynicotinic acid: the compound was prepared according to the method of Y.S. Lo (Synthetic Communications, 1989, 553). Bromine (0.77 eq.) was slowly added dropwise to a stirred solution of 50% NaOH (2.4 eq.) in water (1 M solution) at 0 °C. After 5 min, 50% NaOH (3 eq.) was appended to the mixture, followed by the addition of solid 2-hydroxynicotinic acid (1 eq.) and the resultant solution was stirred continuously at 50 °C. After 20 h, a mixture of bromine ( 0.38 eq.) and a pre-prepared solution of 50% NaOH (1.2 eq.) in water (1 M solution) and continued stirring at 50 °C for 24 hours. Upon completion of the reaction, the mixture was cooled to 0 °C and acidified to pH 2 with concentrated hydrochloric acid to precipitate the solid product. The solid was separated by filtration, washed sequentially with warm water/isopropanol (3:1) and ether, and dried to give 5-bromo-2-hydroxynicotinic acid in 87% yield as an off-white solid. The product characterization data were as follows: 1H NMR (400 MHz, DMSO) δ 8.25 (1H, d, J = 2.7 Hz), 8.33 (1H, d, J = 2.7 Hz), 13.84 (2H, bs); 13C NMR (400 MHz, DMSO) δ 99.45, 117.97, 142.01, 147.42, 163.22, 163.88; MS (ES-) m/z 218-216 (M-H)-. |
| References | [1] Patent: WO2004/110442, 2004, A1. Location in patent: Page 17; 18 [2] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 9, p. 2566 - 2569 [3] Patent: US2002/161000, 2002, A1 [4] Patent: US2006/287292, 2006, A1. Location in patent: Page/Page column 26 [5] Organic Process Research and Development, 2008, vol. 12, # 4, p. 603 - 613 |
5-Bromo-2-hydroxynicotinic acid Preparation Products And Raw materials
| Raw materials | 2-Hydroxynicotinic acid-->Hydrochloric acid-->Sodium hydroxide |
| Preparation Products | 5-Bromo-2-chloronicotinic acid-->5-BROMO-2-CHLORO-N,N-DIMETHYL-3-PYRIDINECARBOXAMIDE |
