| Identification | More | [Name]
5-BROMO-2-METHOXY-NICOTINIC ACID | [CAS]
54916-66-4 | [Synonyms]
5-BROMO-2-METHOXY-3-PYRIDINECARBOXYLIC ACID
5-BROMO-2-METHOXY-NICOTINIC ACID
5-Bromo-2-methoxypyridine-3-carboxylic acid
5-Bromo-2-methoxynicotinic acid 98% | [Molecular Formula]
C7H6BrNO3 | [MDL Number]
MFCD06656771 | [Molecular Weight]
232.03 | [MOL File]
54916-66-4.mol |
| Chemical Properties | Back Directory | [Melting point ]
156-158 | [Boiling point ]
324.8±42.0 °C(Predicted) | [density ]
1.713 | [storage temp. ]
Keep Cold | [form ]
solid | [pka]
2.97±0.10(Predicted) | [Appearance]
White to off-white Solid | [InChI]
InChI=1S/C7H6BrNO3/c1-12-6-5(7(10)11)2-4(8)3-9-6/h2-3H,1H3,(H,10,11) | [InChIKey]
SJLXURQPRRMPIV-UHFFFAOYSA-N | [SMILES]
C1(OC)=NC=C(Br)C=C1C(O)=O | [CAS DataBase Reference]
54916-66-4(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Uses]
5-Bromo-2-methoxy-nicotinic acid is used as an intermediate in pharmaceutical synthesis and can be employed to prepare RXFP1 receptor agonists. Its synthetic products can selectively activate the RXFP1 receptor for the treatment of heart failure, with an EC50 value of approximately 6.3nM. | [Synthesis]
General procedure for the synthesis of 5-bromo-2-methoxynicotinic acid from 2-methoxynicotinic acid: 2-methoxynicotinic acid (20 g, 130.60 mmol) was dissolved in H2O (1500 mL) at room temperature, followed by slow addition of Br2 (20 mL, 375.45 mmol). The reaction mixture was stirred continuously at room temperature overnight. Upon completion of the reaction, the solid product was collected by filtration and washed thoroughly with deionized water and finally dried to afford 5-bromo-2-methoxynicotinic acid (25 g, 82% yield). The structure of the product was confirmed by 1H-NMR (DMSO-d6, 400 MHz) and mass spectrometry (MS): 1H-NMR δ 13.33 (br s, 1H), 8.47 (d, J = 2.4 Hz, 1H), 8.21 (d, J = 2.4 Hz, 1H), 3.90 (s, 3H); MS (M + H)+ m/z: 232/234. | [References]
[1] Patent: WO2013/33971, 2013, A1. Location in patent: Page/Page column 144
[2] Patent: US2014/213571, 2014, A1. Location in patent: Paragraph 0572 |
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