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| | 2,6-Dibromopyridine-4-carboxylic acid Basic information |
| Product Name: | 2,6-Dibromopyridine-4-carboxylic acid | | Synonyms: | 2,6-Dibromo-4-pyridinecarboxylic acid;2,6-Dibromoopyridine-4-carboxylic acid;2,6-Dibromopyridine-4-carboxylic acid;Isonicotinicacid, 2,6-dibromo- (6CI,7CI,8CI);2,6-DibroMopyridine-4-car...;DibroMopyridine-4-carboxylic acid;2,6-Dibromopyridine-4-carboxylic acid, 4-Carboxy-2,6-dibromopyridine;2,6-DibroMoisonicotinic acid, 95+% | | CAS: | 2016-99-1 | | MF: | C6H3Br2NO2 | | MW: | 280.9 | | EINECS: | 640-910-0 | | Product Categories: | Pyridines;pharmacetical | | Mol File: | 2016-99-1.mol |  |
| | 2,6-Dibromopyridine-4-carboxylic acid Chemical Properties |
| Melting point | 184-185 °C(Solv: water (7732-18-5)) | | Boiling point | 487.5±45.0 °C(Predicted) | | density | 2.202±0.06 g/cm3(Predicted) | | storage temp. | under inert gas (nitrogen or Argon) at 2-8°C | | form | solid | | pka | 2.59±0.10(Predicted) | | color | White to off white | | InChI | InChI=1S/C6H3Br2NO2/c7-4-1-3(6(10)11)2-5(8)9-4/h1-2H,(H,10,11) | | InChIKey | AULQTVXAKNKCCA-UHFFFAOYSA-N | | SMILES | C1(Br)=NC(Br)=CC(C(O)=O)=C1 |
| Hazard Codes | Xi | | HS Code | 2933399990 |
| | 2,6-Dibromopyridine-4-carboxylic acid Usage And Synthesis |
| Chemical Properties | Pale yellow solid | | Uses | 2,6-Dibromopyridine-4-carboxylic Acid is an analog of 2,6-Dichloroisonicotinic acid which binds and inhibits tobacco catalase activity. | | Synthesis | General procedure for the synthesis of 2,6-dibromopyridine-4-carboxylic acid from citrazinic acid: Citrazinic acid (2.33 g, 0.015 mol) was mixed with phosphorus tribromide and heated to 180 °C under nitrogen protection for 3 hours. After completion of the reaction, the reaction mixture was cooled and quenched carefully with ice water. The reaction mixture was filtered and the aqueous phase was extracted with dichloromethane (4 x 40 ml). The solid fraction was continuously extracted in a Soxhlet extractor using dichloromethane for 12 hours. The directly extracted organic phase was dried with anhydrous sodium sulfate, filtered and concentrated to give 2.2 g of slightly red solid. The organic phase of Soxhlet extraction was similarly dried with anhydrous sodium sulfate, filtered and concentrated to give 0.5 g of a slightly red solid. The two fractions of 2,6-dibromoisonicotinic acid (64% total yield) were combined after confirmation of structural identity by NMR hydrogen spectroscopy (CDCl3, δ 8.04, 2H, s). | | References | [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 12, p. 5079 - 5093
[2] Tetrahedron, 2007, vol. 63, # 2, p. 291 - 298
[3] Organic and Biomolecular Chemistry, 2005, vol. 3, # 8, p. 1460 - 1467
[4] Patent: WO2005/84439, 2005, A1. Location in patent: Page/Page column 35
[5] Synthesis, 2000, # 8, p. 1138 - 1142 |
| | 2,6-Dibromopyridine-4-carboxylic acid Preparation Products And Raw materials |
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