| Identification | Back Directory | [Name]
3-Bromo-1,5-naphthyridine | [CAS]
17965-71-8 | [Synonyms]
3-broMo-1
5-naphthyridine
3-Bromo-1,5phthyridine
3-bromo-1, 5-naphthidine
3-bromo-1,5-naphthyridine
1,5-Naphthyridine,3-bromo- | [Molecular Formula]
C8H5BrN2 | [MDL Number]
MFCD11858569 | [MOL File]
17965-71-8.mol | [Molecular Weight]
209.04 |
| Chemical Properties | Back Directory | [Boiling point ]
289 °C | [density ]
1.656 | [Fp ]
129 °C | [storage temp. ]
Sealed in dry,Room Temperature | [pka]
1.43±0.10(Predicted) | [Appearance]
Brown to black Solid | [InChI]
InChI=1S/C8H5BrN2/c9-6-4-8-7(11-5-6)2-1-3-10-8/h1-5H | [InChIKey]
DQTDPFYKQAQVJU-UHFFFAOYSA-N | [SMILES]
N1C2C(=NC=CC=2)C=C(Br)C=1 |
| Hazard Information | Back Directory | [Synthesis]
General procedure for the synthesis of 3-bromo-1,5-naphthyridine from 1,5-naphthyridine: To a 10 mL solution of glacial acetic acid containing compound 4 (2.7 g, 20.76 mmol) and NaOAc (3.41 g, 41.52 mmol), stirred at 85 °C, 1 M of bromine in acetic acid (35 mL) was slowly added, and the reaction lasted for 5 hours. Upon completion of the reaction, the mixture was cooled to room temperature and the acetic acid was removed by vacuum concentration. The product was purified by column chromatography (petroleum ether/ethyl acetate = 2:1) to give compound 5 (2.36 g, 55% yield) as a white solid. Melting point: 107-108 °C (literature value: 108-109 °C).1H NMR (400 MHz, CDCl3): δ 8.96 (d, J = 2.1 Hz, 2H), 8.56 (s, 1H), 8.36 (d, J = 8.5 Hz, 1H), 7.69-7.56 (m, 1H). | [References]
[1] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 16, p. 3251 - 3255
[2] Patent: WO2011/149937, 2011, A1. Location in patent: Page/Page column 39; 75
[3] Patent: WO2013/78441, 2013, A1. Location in patent: Paragraph 00143; 00305
[4] Patent: WO2008/82487, 2008, A2. Location in patent: Page/Page column 108
[5] Patent: WO2011/15343, 2011, A1. Location in patent: Page/Page column 40 |
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