| Identification | More | [Name]
1,5-NAPHTHYRIDINE | [CAS]
254-79-5 | [Synonyms]
1,5-DIAZANAPHTHALENE
1,5-NAPHTHYRIDINE
PYRIDO[1,5-B]PYRIDINE
1,5-Pyridopyridine
1,5-Naphthyridine(6CI,8CI,9CI)
Pyrido[3,2-b]pyridine | [Molecular Formula]
C8H6N2 | [MDL Number]
MFCD00039727 | [Molecular Weight]
130.15 | [MOL File]
254-79-5.mol |
| Chemical Properties | Back Directory | [Melting point ]
69-75 °C | [Boiling point ]
152 °C / 54mmHg | [density ]
1.25 | [refractive index ]
1.6231 (estimate) | [storage temp. ]
Sealed in dry,Room Temperature | [form ]
Solid | [pka]
2.90±0.10(Predicted) | [color ]
Off-white | [InChI]
InChI=1S/C8H6N2/c1-3-7-8(9-5-1)4-2-6-10-7/h1-6H | [InChIKey]
VMLKTERJLVWEJJ-UHFFFAOYSA-N | [SMILES]
N1C2C(=NC=CC=2)C=CC=1 | [CAS DataBase Reference]
254-79-5(CAS DataBase Reference) | [NIST Chemistry Reference]
1,5-Naphthyridine(254-79-5) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R41:Risk of serious damage to eyes.
R37/38:Irritating to respiratory system and skin .
R22:Harmful if swallowed. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S39:Wear eye/face protection . | [WGK Germany ]
3 | [HS Code ]
29339900 |
| Hazard Information | Back Directory | [Chemical Properties]
off-whtie solid | [Definition]
ChEBI: 1,5-naphthyridine is a naphthyridine. | [Synthesis]
Synthesis of 1,5-naphthyridine (4): To a round bottom flask was added 3-aminopyridine (1 g, 10.63 mmol), sodium m-nitrobenzenesulfonate (3.59 g, 15.95 mmol), glycerol (3.33 mL, 46.85 mmol), concentrated sulfuric acid (5.92 mL, 111.53 mmol) and water (3 mL). The reaction mixture was heated to 150 °C and stirred continuously for 2.5 hours. Upon completion of the reaction, it was cooled to room temperature and the pH was adjusted to 8 with 4 M sodium hydroxide solution, followed by extraction with ethyl acetate (5 x 30 mL). The organic phases were combined, washed with saturated saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by column chromatography (petroleum ether/ethyl acetate=1:1) afforded the target product 1,5-naphthyridine (622 mg, 45% yield) as a yellow solid. Melting point: 74~75°C (literature value 75°C). 1H NMR (400MHz, CDCl3): δ9.04-8.96 (m, 2H), 8.43 (d, J=8.4Hz, 2H), 7.66 (dd, J=8.4,4.1Hz, 2H). | [Purification Methods]
Purify 1,5-naphthyridine by repeated sublimation. The picrate crystallises from EtOH with m 200o(dec). [UV: Armarego Physical Methods in Heterocyclic Chemistry (Ed Katritzky, Academic Press) Vol III 133 1971, Beilstein 23 II 178, 23 III/IV 1235.] | [References]
[1] Synthetic Communications, 2011, vol. 41, # 12, p. 1843 - 1851
[2] Tetrahedron Letters, 2002, vol. 43, # 20, p. 3747 - 3750
[3] Organic Letters, 2000, vol. 2, # 7, p. 875 - 878
[4] Chemistry - A European Journal, 2017, vol. 23, # 53, p. 13046 - 13050
[5] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 16, p. 3251 - 3255 |
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